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108-67-8 Usage

Chemical Description

Mesitylene and pentamethylbenzene are both steric hindered aromatic compounds, which means they have bulky substituents that affect their reactivity.

Outline

The molecular structure of mesitylene (also known as mesitylene, molecular formula is C9H12) is σ bond which formed by benzene ring C atoms by means of sp2 hybrid orbital, other C atoms form σ bond by means of sp3 hybrid orbital, it is functional group in the presence of many multi organic compounds. It is aromatic hydrocarbon which obtained by three hydrogens symmetrically-substituted by three methyl in benzene ring.It is widespread in coal tar and certain petroleum. It is colorless liquid, toxic, flammable and explosive. The freezing point is-44.72 ℃, melting point is-44.7 ℃, boiling point is 164.7 ℃, the relative density is 0.8652 (20/4℃). Mesitylene can generate trimesic acid with the oxidation of dilute nitric acid. Pure mesitylene is made by acetone in vapor phase catalytic dehydrationthe at 300~500℃. Mesitylene is important organic chemical raw material, the use of mesitylene can develop three toluene, trimesic acid, benzoic anhydride and other dye intermediates, it can also be used for the production of antioxidants, polyester resin curing agent, stabilizer, alkyd resins and plasticizers. Since mesitylene is a good solvent, and it is flammable, irritant, and it has low freezing point. In the electronics industry, it is used as developer of photosensitive sheet silicone. Mesitylene is also common volatile organic compound (VOC) in city, this is mainly generated by the combustion. It plays an important role (including aerosol and tropospheric ozone generation) in many chemical reactions in the atmosphere. Since the three hydrogens on the aromatic ring have the same chemical environment, in the mesitylene magnetic resonance spectrum hydrogen spectrum only has a single peak which peak area is corresponding to three hydrogen in the vicinity of 6.8ppm. Therefore, mesitylene is sometimes used as internal standard substance in proton nuclear magnetic resonance method which comprises aromatic organic samples. The annual demand of mesitylene is about 100,000 tons in current domestic market. The above information is edited by the lookchem of Wang Xiaodong.

Chemical Properties

Different sources of media describe the Chemical Properties of 108-67-8 differently. You can refer to the following data:
1. It is colorless transparent liquid. It is insoluble in water, soluble in ethanol, it can dissolve in benzene, ether, acetone in any proportion.
2. colourless liquid with an aromatic odour
3. Mesitylene is a clear, colorless liquid. Distinctive, aromatic odor.

Uses

Different sources of media describe the Uses of 108-67-8 differently. You can refer to the following data:
1. It can be used for the production of trimesic acid and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizers and dyes etc. It can be used as raw material of organic synthesis, it can be used in the preparation of trimesic acid, and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizer, 2,4,6-trimethyl aniline reactive brilliant blue, K-3R and other dye. It can be used as analytical reagents, solvents, it can be also used in organic synthesis, etc.
2. Intermediate, including anthraquinone vat dyes, UV oxidation stabilizers for plastics.
3. Mesitylene is used to make plastics and dyes. It acts as a solvent, ligand in organometallic chemistry and precursor to 2,4,6-trimethylaniline. It is also used as a developer for photopatternable silicones due to its solvent properties in the electronics industry. It is used as an internal standard in nuclear magnetic resonance (NMR) samples due to the presence of three equivalent protons in it. It is involved in the production of trimesic acid and antioxygen, epoxy firming agent and polyester resin stabilizers. Further, it is used as an additive and component in aviation gasoline blends.

Production method

1. It is derived by the separation of C9 aromatic hydrocarbon. 2. In the reforming of heavy aromatics the amount of mesitylene is about 11.8%. However, due to its boiling point (164.7 ℃) is extremely close to the boiling point of O-methyl benzene (165.15 ℃), it is difficult to separate for using distillation method. 3.The isomerization method with partial three toluene as raw material can fractionate, and can get mesitylene which the one way yield is 21.6%, the purity is more than 95%, while 4%-7% of by-product is durene, xylene is 9%. The average temperature of reactor bed is 260℃, pressure is 2.35MPa, empty the entire is 1.0h-1, molar ratio of reforming hydrogen and oil is 10: 1, the catalyst is mordenite which lack of aluminum hydrogen form: Cu: Ni: binder = 85.2: 0.5: 15. Under these conditions, the conversion rate of partial three toluene is 46%, selectivity is 47% , one way yield of mesitylene is 21.6%. HF-BF3 is xylene separated and through the method of isomerization by Japanese Mitsubishi Gas Company, by-products contain high concentration of mesitylene of high boiling, the goods can be get by distilled and refined. 4. Acetone in sulfuric acid-catalyzed goes through dehydration synthesis can obtain this goods with the yield of 13%-15%. 4600g (79mol) of industrial acetone is cooled to 0-5℃, and 4160ml concentrated sulfuric acid is added with stirring, the temperature can not exceed 10℃. After addition is completed, cntinue stirring 3-4h, place at room temperature for 18-24h. The product is subjected to steam distillation, mesitylene is separated, then it is washed with alkali, water, and then collect distillation fraction of 210℃, 15g sodium metal is added into this fraction, it is heated to near the boiling point, 2/3 liquid is evaporated. the residue is distilled to 210℃, efficient fractionation collection is done for the 163-167℃ distillate, 430-470g1,3,5-mesitylene can be obtained.

Category

It is flammable liquid.

Toxicity grading

Low toxicity.

Acute toxicity

Inhalation-rat LC50: 24000 mg/m/4 hours.

Stimulus data

Skin-Rabbit 20 mg/24 hours of moderate; Eyes-rabbit 500 mg/24 hr mild.

Flammability hazard characteristics

It is inflammable in case of fire, heat, oxidants; when burning stimulated smoke can generate.

Storage characteristics

Treasury should have ventilation and be low-temperature drying; and it should stored separately with oxidants.

Extinguishing agent

Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Professional standards

TWA 120 mg/m3; STEL 170 mg/m.

Physical properties

Colorless liquid with a peculiar odor. An odor threshold concentration of 170 ppbv was reported by Nagata and Takeuchi (1990).

Definition

ChEBI: A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 3232, 1970 DOI: 10.1021/ja00713a078The Journal of Organic Chemistry, 19, p. 923, 1954 DOI: 10.1021/jo01371a008

General Description

A colorless liquid with a peculiar odor. Insoluble in water and less dense than water. Flash point near 123°F. May be toxic by ingestion and inhalation. Used to make plastics and dyes.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

TRIMETHYLBENZENE is incompatible with the following: Oxidizers, nitric acid .

Hazard

Moderate fire hazard. Toxic by inhalation. Central nervous system impairment, asthma, and hematologic effects.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by inhalation. Moderately toxic by intraperitoneal route. Human systemic effects by inhalation: sensory changes involving peripheral nerves, somnolence (general depressed activity), and structural or functional change in trachea or bronchi. Reports of leukopenia and thrombocytopenia in experimental animals. A mild skin and eye irritant. A flammable liquid when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with HNO3. To fight fire, use water spray, fog, foam, CO2. Emitted from modern buildmg materials (CENEAR 69,22,91). When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Mesitylene is used as raw material in chemical synthesis and as ultraviolet stabilizer; as a paint thinner, solvent, and motor fuel component; as an intermediate in organic chemical manufacture.

Source

Detected in distilled water-soluble fractions of 87 octane gasoline (0.34 mg/L), 94 octane gasoline (1.29 mg/L), Gasohol (0.48 mg/L), No. 2 fuel oil (0.08 mg/L), jet fuel A (0.09 mg/L), diesel fuel (0.03 mg/L), and military jet fuel JP-4 (0.09 mg/L) (Potter, 1996). Schauer et al. (1999) reported 1,3,5-trimethylbenzene in a diesel-powered medium-duty truck exhaust at an emission rate of 260 μg/km. California Phase II reformulated gasoline contained 1,3,5-trimethylbenzene at a concentration of 7.45 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 1.98 and 210 mg/km, respectively (Schauer et al., 2002). Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average 1,3,5-trimethylbenzene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 333, 86, and 13 μg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average 1,3,5- trimethylbenzene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were greater, i.e., 441, 91, and 27 μg/L, respectively. Drinking water standard: No MCLGs or MCLs have been proposed (U.S. EPA, 2000).

Environmental fate

Biological. In anoxic groundwater near Bemidji, MI, 1,3,5-trimethylbenzene anaerobically biodegraded to the intermediate tentatively identified as 3,5-dimethylbenzoic acid (Cozzarelli et al., 1990). Photolytic. Glyoxal, methylglyoxal, and biacetyl were produced from the photooxidation of 1,3,5-trimethylbenzene by OH radicals in air at 25 °C (Tuazon et al., 1986a). The rate constant for the reaction of 1,3,5-trimethylbenzene and OH radicals at room temperature was 4.72 x 10-11 cm3/molecule?sec (Hansen et al., 1975). A rate constant of 2.97 x 10-8 L/molecule?sec was reported for the reaction of 1,3,5-trimethylbenzene with OH radicals in the gas phase (Darnall et al., 1976). Similarly, a room temperature rate constant of 6.05 x 10-11 cm3/molecule?sec was reported for the vapor-phase reaction of 1,3,5-trimethylbenzene with OH radicals (Atkinson, 1985). At 25 °C, a rate constant of 3.87 x 10-11 cm3/molecule?sec was reported for the same reaction (Ohta and Ohyama, 1985). Chemical/Physical. 1,3,5-Trimethylbenzene will not hydrolyze because it does not contain a hydrolyzable functional group (Kollig, 1993).

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Purification Methods

Dry it with CaCl2 and distil it from Na in a glass helices-packed column. Treat it with silica gel and redistil it. Alternative purifications include vapour-phase chromatography, or fractional distillation followed by azeotropic distillation with 2-methoxyethanol (which is subsequently washed out with H2O), drying and fractional distilling. More exhaustive purification uses sulfonation by dissolving in two volumes of conc H2SO4, precipitating with four volumes of conc HCl at 0o, washing with conc HCl and recrystallising from CHCl3. The mesitylene sulfonic acid is hydrolysed with boiling 20% HCl and steam distilled. The separated mesitylene is dried (MgSO4 or CaSO4) and distilled. It can also be fractionally crystallised from the melt at low temperatures. [Beilstein 5 IV 1016.]

Incompatibilities

Vapors forms explosive mixture with air. Violent reaction with nitric acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 108-67-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 108-67:
(5*1)+(4*0)+(3*8)+(2*6)+(1*7)=48
48 % 10 = 8
So 108-67-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3

108-67-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T0470)  1,3,5-Trimethylbenzene  >97.0%(GC)

  • 108-67-8

  • 25mL

  • 120.00CNY

  • Detail
  • TCI America

  • (T0470)  1,3,5-Trimethylbenzene  >97.0%(GC)

  • 108-67-8

  • 500mL

  • 395.00CNY

  • Detail
  • Alfa Aesar

  • (A11323)  Mesitylene, 98+%   

  • 108-67-8

  • 100ml

  • 311.0CNY

  • Detail
  • Alfa Aesar

  • (A11323)  Mesitylene, 98+%   

  • 108-67-8

  • 500ml

  • 496.0CNY

  • Detail
  • Alfa Aesar

  • (A11323)  Mesitylene, 98+%   

  • 108-67-8

  • 2500ml

  • 1643.0CNY

  • Detail
  • Sigma-Aldrich

  • (61927)  Mesitylene  certified reference material, TraceCERT®

  • 108-67-8

  • 61927-100MG

  • 816.66CNY

  • Detail
  • Supelco

  • (41103)  1,3,5-Trimethylbenzenesolution  certified reference material, 5000 μg/mL in methanol

  • 108-67-8

  • 000000000000041103

  • 524.16CNY

  • Detail
  • Sigma-Aldrich

  • (63908)  Mesitylene  analytical standard

  • 108-67-8

  • 63908-5ML

  • 2,033.46CNY

  • Detail
  • Sigma-Aldrich

  • (M7200)  Mesitylene  98%

  • 108-67-8

  • M7200-5ML

  • 398.97CNY

  • Detail
  • Sigma-Aldrich

  • (M7200)  Mesitylene  98%

  • 108-67-8

  • M7200-100ML

  • 522.99CNY

  • Detail
  • Sigma-Aldrich

  • (M7200)  Mesitylene  98%

  • 108-67-8

  • M7200-500ML

  • 1,021.41CNY

  • Detail
  • Sigma-Aldrich

  • (M7200)  Mesitylene  98%

  • 108-67-8

  • M7200-2.5L

  • 2,331.81CNY

  • Detail

108-67-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3,5-trimethylbenzene

1.2 Other means of identification

Product number -
Other names 2,4,6-Me3-Ph

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fuels and fuel additives,Intermediates,Paint additives and coating additives not described by other categories,Solvents (for cleaning or degreasing),Solvents (which become part of product formulation or mixture)
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-67-8 SDS

108-67-8Synthetic route

(2,4,6-trimethylphenyl) phenyl sulfone
3112-82-1

(2,4,6-trimethylphenyl) phenyl sulfone

A

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide for 2h; Ambient temperature;A 99%
B 100%
C31H38OSi
85656-15-1

C31H38OSi

A

1,2,3,3-tetramethyl-1H-indene
4705-87-7

1,2,3,3-tetramethyl-1H-indene

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
electrlysis, at 1.5 V, electrolyte: tetrabutylammonium perchlorate, in CH2Cl2;A 100%
B 166 %
In dichloromethane electrolysis, at 1.5 V; electrolyte: tetrabutylammonium perchlorate;A 100%
B 166 %
morpholine
110-91-8

morpholine

mesitylcopper(I)
75732-01-3

mesitylcopper(I)

A

C4H8NO(1-)*Cu(1+)
77590-49-9

C4H8NO(1-)*Cu(1+)

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of amine;; evapd. or filtered; elem. anal.;;A n/a
B 100%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

ammonia
7664-41-7

ammonia

A

amino-copper
77590-45-5

amino-copper

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of NH3;; evapd. or filtered; elem. anal.;;A n/a
B 100%
2,4,6-trimethylphenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-43-1

2,4,6-trimethylphenyl(m-carboran-9-yl)iodonium tetrafluoroborate

sodium chloride
7647-14-5

sodium chloride

A

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

B

9-chloro-m-carborane
17819-85-1

9-chloro-m-carborane

C

iodomesitylene
4028-63-1

iodomesitylene

D

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 2.5 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 0%
B 100%
C 100%
D 0%
hexyl 2,4,6-trimethylbenzenesulfonate
82965-02-4

hexyl 2,4,6-trimethylbenzenesulfonate

A

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene Product distribution; Mechanism; further solvents;A 85%
B 99%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran; water at 80℃; for 8h; Time; Schlenk technique; Sealed tube; Inert atmosphere;99%
With [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride; isopropyl alcohol; sodium t-butanolate at 100℃; for 48h; Inert atmosphere; Sealed tube; Green chemistry;89%
With isopropyl alcohol at 20℃; for 24h; UV-irradiation; chemoselective reaction;88%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

N-butylamine
109-73-9

N-butylamine

A

copper(I) n-butylamide
77590-46-6

copper(I) n-butylamide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of amine;; evapd. or filtered; elem. anal.;;A n/a
B 98%
dimesityl sulfone
3112-79-6

dimesityl sulfone

A

2,4,6-trimethylbenzenesulphinic acid
59057-35-1

2,4,6-trimethylbenzenesulphinic acid

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide for 2h; Ambient temperature;A 92%
B 97%
p-benzoquinone
106-51-4

p-benzoquinone

2-mesitylmagnesium bromide
2633-66-1

2-mesitylmagnesium bromide

A

4-hydroxy-4-(2,4,6-trimethylphenyl)-2,5-cyclohexadiene

4-hydroxy-4-(2,4,6-trimethylphenyl)-2,5-cyclohexadiene

B

hydroquinone
123-31-9

hydroquinone

C

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran Grignard reaction;A 97%
B 3%
C 4%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

dibutylamine
111-92-2

dibutylamine

A

copper(I) N,N-di-n-butylamide
77590-48-8

copper(I) N,N-di-n-butylamide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., stirring overnight;; evapd. in vac., washed with hexane, dried in vac., crystd. from hexane at -15°C; elem. anal.;;A n/a
B 95%
2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

mesitylboronic acid
5980-97-2

mesitylboronic acid

A

2,2',4,6-tetramethylbiphenyl
89970-02-5

2,2',4,6-tetramethylbiphenyl

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In toluene at 90℃; for 37h; Suzuki cross-coupling; Title compound not separated from byproducts.;A 93%
B 5%
ethylmesitylsilane

ethylmesitylsilane

A

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

B

ethyl iodosilane

ethyl iodosilane

Conditions
ConditionsYield
With hydrogen iodide at -35℃; for 168000h; sealed tube;A n/a
B 92%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

diethylamine
109-89-7

diethylamine

A

copper(I) N,N-diethylamide
71426-07-8

copper(I) N,N-diethylamide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of amine;; evapd. or filtered; elem. anal.;;A n/a
B 92%
mesitylenecarboxylic acid
480-63-7

mesitylenecarboxylic acid

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 140℃; for 20h;90%
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction;90%
With Nafion-H In toluene at 100℃; for 12h;80%
piperidine
110-89-4

piperidine

mesitylcopper(I)
75732-01-3

mesitylcopper(I)

A

copper piperidide
73680-02-1

copper piperidide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of amine;; evapd. or filtered; elem. anal.;;A n/a
B 90%
hexyl 2,4,6-trimethylbenzenesulfonate
82965-02-4

hexyl 2,4,6-trimethylbenzenesulfonate

A

lithium 2,4,6-trimethylbenzenesulfinate
145385-15-5

lithium 2,4,6-trimethylbenzenesulfinate

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

C

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In 1,4-dioxane; toluene Product distribution; Mechanism; further solvents;A 21%
B 61%
C 88%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

aniline
62-53-3

aniline

A

copper(I) anilide
77590-50-2

copper(I) anilide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of aniline;; evapd. or filtered; elem. anal.;;A n/a
B 88%
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

tert-butylamine
75-64-9

tert-butylamine

A

copper(I) t-butylamide
77590-47-7

copper(I) t-butylamide

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran THF, ambient temp., excess of amine;; evapd. or filtered; elem. anal.;;A n/a
B 87%
hexyl 2,4,6-trimethylbenzenesulfonate
82965-02-4

hexyl 2,4,6-trimethylbenzenesulfonate

A

2,4,6-trimethylbenzenesulphinic acid
59057-35-1

2,4,6-trimethylbenzenesulphinic acid

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

C

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In 1,4-dioxane at 23℃; for 2h;A 69%
B 10%
C 85%
C23H26BF6O(1-)*K(1+)

C23H26BF6O(1-)*K(1+)

A

C5H3F5
1547-23-5

C5H3F5

B

1,1,1-trifluoro-2-trifluoromethyl-2-butene
21223-06-3

1,1,1-trifluoro-2-trifluoromethyl-2-butene

C

4,4,4-Trifluoro-3-trifluoromethyl-but-1-ene

4,4,4-Trifluoro-3-trifluoromethyl-but-1-ene

D

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In solid at 200℃; under 0.07 Torr; for 0.0125h;A 11%
B 48%
C 3%
D 83%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

trimethylstannane
1631-73-8

trimethylstannane

A

n-butyltrimethyltin
1527-99-7

n-butyltrimethyltin

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With n-butyllithium In hexane 2-bromomesitylene (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 5 h at reflux temp., quenched with water; analyzed by GC;A 83%
B 38%
With n-butyllithium In hexane 2-bromomesitylene (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;A 33%
B 11%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

A

1-fluoro-2,4,6-trimethylbenzene
392-69-8

1-fluoro-2,4,6-trimethylbenzene

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
Stage #1: 2,4,6-trimethylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Flow reactor;
Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at 0℃; Reagent/catalyst; Flow reactor;
A 82%
B 10%
cyanomesitylene
2571-52-0

cyanomesitylene

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In ethyl-cyclohexane at 160℃; for 15h; Inert atmosphere;81%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 160℃; for 15h; Inert atmosphere;81%
1-fluoro-2,4,6-trimethylbenzene
392-69-8

1-fluoro-2,4,6-trimethylbenzene

potassium enolate of acetone
128190-66-9, 25088-58-8

potassium enolate of acetone

A

1-(2,4,6-trimethylphenyl)-2-propanone
42797-68-2

1-(2,4,6-trimethylphenyl)-2-propanone

B

1-(2,4,6-Trimethylphenyl)-2-propanol
27645-30-3

1-(2,4,6-Trimethylphenyl)-2-propanol

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

D

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With ammonia; potassium amide at -33℃; Product distribution; Rate constant;A 2.8%
B 5.6%
C 11.7%
D 80%
With ammonia; potassium amide at -33℃;A 1.8 % Chromat.
B 3.1 % Chromat.
C 18.2 % Chromat.
D 77 % Chromat.
With ammonia; potassium amide at -33℃;A 2.8 % Chromat.
B 5.6 % Chromat.
C 11.7 % Chromat.
D 80 % Chromat.
bis(mesityl)(η8-cyclo-octatetraene)zirconium(IV)*0.5Et2O

bis(mesityl)(η8-cyclo-octatetraene)zirconium(IV)*0.5Et2O

A

bis{zirconium(IV)(η8-cyclooctatetraene)(μ-2,4-dimethyl-6-CH2C6H2)}

bis{zirconium(IV)(η8-cyclooctatetraene)(μ-2,4-dimethyl-6-CH2C6H2)}

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In diethyl ether complex is suspended in Et2O at room temp. for 2 d, thermal decomposition (N2); elem. anal.;A 50%
B 78%
2,4,6-trimethylphenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-43-1

2,4,6-trimethylphenyl(m-carboran-9-yl)iodonium tetrafluoroborate

sodium fluoride

sodium fluoride

A

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

B

9-fluoro-m-carborane
73050-37-0

9-fluoro-m-carborane

C

iodomesitylene
4028-63-1

iodomesitylene

D

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 2.5 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 16%
B 78%
C 75%
D 14%
1,3-dimethyl-5-methylenecyclohexane
85014-36-4

1,3-dimethyl-5-methylenecyclohexane

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With n-butyllithium; potassium 2-methylbutan-2-olate Mechanism; 1) r.t., 16 h, 2) reflux, 6 h; further reagent: D2O;76%
bis(mesitylene)vanadium(0)
1272-71-5

bis(mesitylene)vanadium(0)

A

Tetrakis(pyridin)-dichlorovanadin(II)
25377-37-1, 27790-75-6, 82009-22-1

Tetrakis(pyridin)-dichlorovanadin(II)

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With pyridine; 3-chloroprop-1-ene In toluene soln. of V-complex in toluene was treated with CH2=CHCH2Cl (inert atmosphere), the mixt. was stirred at room temp. for 24 h; the mother liquor contained org. compounds, products of the reaction of CH2=CHCH2Cl with either toluene or mesitylene (CLG-MS); filtered, ppt. was dissolved in pyridine, soln. was filtered and concd.to give the crystals of VCl2*4Py; identified by comparison of the IR spectrum with that of authentic sample;A 75%
B 75%
methanol
67-56-1

methanol

acetone
67-64-1

acetone

A

pentamethylbenzene,
700-12-9

pentamethylbenzene,

B

Hexamethylbenzene
87-85-4

Hexamethylbenzene

C

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With aluminum oxide at 420℃; flowrate: 33 ml/ h;A n/a
B 74%
C n/a
benzoyl chloride
98-88-4

benzoyl chloride

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-Trimethylbenzophenon
954-16-5

2,4,6-Trimethylbenzophenon

Conditions
ConditionsYield
With iron oxide supported on HY zeolite In neat (no solvent) at 110℃; for 3h; Friedel-Crafts Acylation;100%
With iodine; phosphorus trichloride at 160℃; for 36h; Inert atmosphere;99%
With C4F9SO3H at 165℃; for 2h;98%
acetic acid
64-19-7

acetic acid

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-Trimethylacetophenone
1667-01-2

2,4,6-Trimethylacetophenone

Conditions
ConditionsYield
With heptafluorobutyric anhydride at 100℃; for 3h; Friedel-Crafts acetylation;100%
With cross-linked polystyrene-supported aluminum triflate at 80℃; for 2.8h; Friedel-Crafts acylation; Neat (no solvent); chemoselective reaction;94%
With trifluoromethylsulfonic anhydride at 20℃; for 0.0666667h; Friedel-Crafts acylation;93%
acetyl chloride
75-36-5

acetyl chloride

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-Trimethylacetophenone
1667-01-2

2,4,6-Trimethylacetophenone

Conditions
ConditionsYield
With hierarchical nanocrystalline zeolite ZSM-5 at 50℃; for 2h; Temperature;100%
With iron(III) oxide at 20℃; for 0.166667h; Friedel Crafts acylation; regioselective reaction;96%
With benzyltributylammonium tetrachloroferrate at 50℃; for 0.0666667h; Friedel-Crafts reaction;94%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

1,3,5-trimethylcyclohexane
1839-63-0

1,3,5-trimethylcyclohexane

Conditions
ConditionsYield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 120℃; under 7600.51 Torr; for 8h;100%
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 160℃; under 37503.8 Torr; for 18h;84%
at 108℃; Thermodynamic data; Hydrogenation;
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

nitromesitylene
603-71-4

nitromesitylene

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -78℃; for 3h; Irradiation;100%
With dinitrogen tetraoxide In dichloromethane at 25℃; for 24h;100%
With nitric acid; sulfuric acid In dichloromethane at 25℃; for 0.03h;100%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-bromomesitylene
1667-04-5

2-bromomesitylene

Conditions
ConditionsYield
With hydrogenchloride; sodium peroxide In acetic acid at 20 - 25℃; for 4h;100%
With 1-Cl+SbCl6- In dichloromethane at 25℃; for 1h;98%
With sodium chlorite; trichloroacetic acid In dichloromethane at 20℃; for 1h; Chlorination;95%
formaldehyd
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene
21988-87-4

1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 95℃; for 12h;100%
With hydrogen bromide; acetic acid at 95℃; for 12h; Inert atmosphere;99%
With sulfuric acid; potassium bromide In acetic acid at 90 - 95℃; for 6h;97%
4-aminofuroxan-3-carboxylic acid azide
166112-18-1

4-aminofuroxan-3-carboxylic acid azide

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

3-azidocarbonyl-4-(2,4,6-trimethylphenylazo)furoxan
433683-21-7

3-azidocarbonyl-4-(2,4,6-trimethylphenylazo)furoxan

Conditions
ConditionsYield
Stage #1: 4-aminofuroxan-3-carboxylic acid azide With phosphoric acid; sulfuric acid; sodium nitrite at 0 - 2℃; for 1h;
Stage #2: 1,3,5-trimethyl-benzene In pyridine at 0 - 20℃;
100%
carbon dioxide
124-38-9

carbon dioxide

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

mesitylenecarboxylic acid
480-63-7

mesitylenecarboxylic acid

Conditions
ConditionsYield
With Et3SiB(C6F5)4 at 20℃; under 22502.3 Torr; for 18h; Reagent/catalyst;100%
With aluminum tri-bromide; Triphenylsilyl chloride at 20℃; under 22502.3 Torr; for 3h; Autoclave;97%
With aluminum (III) chloride at 30℃; under 15001.5 Torr; for 5h; Pressure; Temperature;95.2%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

1-(4-methylphenyl)-1-(2,4,6-trimethylphenyl)ethene
612824-37-0

1-(4-methylphenyl)-1-(2,4,6-trimethylphenyl)ethene

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 30℃; for 24h; Cooling with ice;100%
With Cu-exchanged tungstophosphoric acid at 80℃; for 3h; neat (no solvent); regioselective reaction;91%
With trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 20h;84%
tri-μ-chlorobis[(.eta-benzene)ruthenium(II)] tetrafluoroborate
70316-95-9

tri-μ-chlorobis[(.eta-benzene)ruthenium(II)] tetrafluoroborate

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

(η-benzene)(η-mesitylene)ruthenium tetrafluoroborate

(η-benzene)(η-mesitylene)ruthenium tetrafluoroborate

Conditions
ConditionsYield
In water; trifluoroacetic acid under dry conditions mixt. of Ru complex, mesitylene, and CF3COOH refluxed for 1.5 h, 48% aq. HBF4 added; pptd. by careful addn. of Et2O; elem. anal.;100%
bis(pentafluorophenyl)(η6-anisole)cobalt(II)
86197-44-6

bis(pentafluorophenyl)(η6-anisole)cobalt(II)

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

bis(pentafluorophenyl)(η6-mesitylene)cobalt(II)

bis(pentafluorophenyl)(η6-mesitylene)cobalt(II)

Conditions
ConditionsYield
In chloroform-d1 byproducts: anisole; mol. ratio 1/1; not isolated, detected by NMR;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

ethyl 1,3,5-trimethylcyclohepta-1,3,5-triene-7-carboxylate

ethyl 1,3,5-trimethylcyclohepta-1,3,5-triene-7-carboxylate

Conditions
ConditionsYield
With Ag3(μ2-(3,5-(CF3)2PyrPy))3 In dichloromethane at 20℃; Buchner Ring Enlargement;100%
With dirhodium tetraacetate In dichloromethane at 25℃; for 60h; Buchner Ring Enlargement; Inert atmosphere;77%
Stage #1: 1,3,5-trimethyl-benzene With dirhodium tetraacetate In dichloromethane Inert atmosphere;
Stage #2: diazoacetic acid ethyl ester In dichloromethane at 23℃; for 60h; Inert atmosphere;
77%
(η6-toluene)Ni(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

(η6-toluene)Ni(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

[(η6-mesitylene)Ni(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]

[(η6-mesitylene)Ni(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]

Conditions
ConditionsYield
In pentane at 20℃; Inert atmosphere;100%
1,3-dihydroxy-1H-1λ3-benzo[d][1,2]iodoxol-1-yl trifluoromethanesulfonate

1,3-dihydroxy-1H-1λ3-benzo[d][1,2]iodoxol-1-yl trifluoromethanesulfonate

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-(mesityl-λ3-iodanyl)benzoic acid triflate salt

2-(mesityl-λ3-iodanyl)benzoic acid triflate salt

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 24h; Inert atmosphere;100%
In 2,2,2-trifluoroethanol at 20℃; for 24h;89%
2-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-yn-1-yl)phenol

2-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-yn-1-yl)phenol

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

4-mesityl-2-phenyl-2-(trifluoromethyl)-2H-chromene

4-mesityl-2-phenyl-2-(trifluoromethyl)-2H-chromene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 50℃; for 16h;100%
acetic anhydride
108-24-7

acetic anhydride

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-Trimethylacetophenone
1667-01-2

2,4,6-Trimethylacetophenone

Conditions
ConditionsYield
With indium(III) triflate; lithium perchlorate In nitromethane at 20℃;99%
With antimonypentachloride; lithium perchlorate In dichloromethane for 0.5h; Heating;95%
With nano-sulfated titania at 50℃; for 1h; Friedel Crafts acylation; neat (no solvent);95%
benzoic acid
65-85-0

benzoic acid

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-Trimethylbenzophenon
954-16-5

2,4,6-Trimethylbenzophenon

Conditions
ConditionsYield
With trifluoroacetic anhydride; bismuth(lll) trifluoromethanesulfonate at 30℃; for 12h; Friedel-Crafts acetylation;99%
With pyridin-2-yl trifluoromethanesulfonate; trifluoroacetic acid for 5h; Heating;96%
With cross-linked polystyrene-supported aluminum triflate at 80℃; for 2.9h; Friedel-Crafts acylation; Neat (no solvent); chemoselective reaction;93%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

iodomesitylene
4028-63-1

iodomesitylene

Conditions
ConditionsYield
With tetrafluoroboric acid; [bis(pyridine)iodine]+ tetrafluoroborate In diethyl ether; dichloromethane for 0.1h; Ambient temperature;99%
With Oxone; potassium iodide In methanol at 20℃; for 24h;99%
With ammonium nitrate; sulfuric acid; iodine In water; acetonitrile at 60℃; for 0.166667h; regioselective reaction;98%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4-diiodomesitylene
53779-84-3

2,4-diiodomesitylene

Conditions
ConditionsYield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid at 70℃; for 28h;99%
With iodine; 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile for 18h; Ambient temperature;99%
With iodine; 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile for 16h; Ambient temperature;99%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide; perchloric acid In tetrachloromethane for 22h; Ambient temperature;99%
With hydrogen bromide; dihydrogen peroxide In water at 20℃; for 24h; Darkness;98%
With gold(III) chloride; N-Bromosuccinimide In dichloromethane at 20℃; for 12h; Inert atmosphere;98%
4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6,4'-tetramethylbenzophenone
1146-84-5

2,4,6,4'-tetramethylbenzophenone

Conditions
ConditionsYield
With C4F9SO3H at 165℃; for 2h;99%
With In(OSO2CF3)3 for 0.0666667h; Friedel-Crafts acylation reaction; microwave irradiation;88%
With copper(II) ferrite In neat (no solvent) at 80℃; for 18h; Friedel-Crafts Acylation;79%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

dimesityl sulfone
3112-79-6

dimesityl sulfone

Conditions
ConditionsYield
With sulfuric acid; trifluoroacetic anhydride99%
With trifluoromethylsulfonic anhydride; bis(N-methylpyridinium) sulfate for 0.0833333h;95%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

/PBXSD024-1560/

/PBXSD024-1560/

/PBXSD024-1570/

/PBXSD024-1570/

A

4-nitro-o-xylene
99-51-4

4-nitro-o-xylene

B

2-nitro-2',4,4',5,6'-pentamethylbiphenyl
99321-72-9

2-nitro-2',4,4',5,6'-pentamethylbiphenyl

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0166667h;A 1%
B 99%

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Fabrication of porous carbons from Mesitylene (cas 108-67-8) for highly efficient CO2 capture: A rational choice improving the carbon loop08/20/2019

Mesitylene, a representative heavy carbon by-product in the course of C1 chemical downstream processes, is proposed to be employed in this study, as the initial material to synthesize the porous carbons that have played a crucial part in the adsorptive carbon capture process but are generally ma...detailed

Compact and easy to use Mesitylene (cas 108-67-8) cold neutron moderator for CANS08/19/2019

Organic aromatic cold neutron moderators - like mesitylene (C9H12) - are often much more convenient to handle and to commission than cryogenic methane or ortho/para hydrogen moderators. Although this benefit comes at the cost of reduced brilliance, mesitylene moderators are suited to enable cold...detailed

108-67-8Relevant articles and documents

ON THE REACTIVITY OF V(η-C6H3Me3-1,3,5)2I

Aviles, T.,Teuben, J.H.

, p. 39 - 44 (1983)

V(η-C6H3Me3-1,3,5)2I reacts with reducing agents such as MeLi, Na or Na to yield the neutral complex V(η-C6H3Me3-1,3,5)2 in 70-75percent yield.Reaction of V(η-C6H3Me3-1,3,5)2I with compounds containing suitable donor atoms such as THF,

Radioactive hydrocarbons [6]

Grosse,Weinhouse

, p. 402 - 403 (1946)

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Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol

Haibach, Michael C.,Stoltz, Brian M.,Grubbs, Robert H.

, p. 15123 - 15126 (2017)

Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan-2-ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin-based conditions for these reductions.

One-Electron Oxidation of Alkylbenzenes in Acetonitrile by Photochemically Produced NO3.: Evidence for an Inner-Sphere Mechanism

Giacco, Tiziana Del,Baciocchi, Enrico,Steenken, Steen

, p. 5451 - 5456 (1993)

The reaction between NO3. and polyalkylbenzenes was studied using 308-nm laser flash photolysis of cerium(IV) ammonium nitrate in the presence of the alkylbenzenes in acetonitrile solution.For all benzenes, with the exception of monoalkylbenzenes and o- and m-xylene, the reaction with NO3. was found to yield the corresponding radical cations and to proceed in an apparently straightforward bimolecular manner.For monoalkylbenzenes and o- and m-xylene, radicals were seen which are derived from the parents by formal loss of H. from the side chain of the aromatic.This reaction proceeds via a complex between the aromatic and NO3. with the decomposition of the complex being rate determining at higher concentrations of aromatic (rate constants for decomposition between 6 * 105 and 4 * 107 s-1).In the complex, electron transfer from the aromatic to NO3. is suggested to be concerted with deprotonation of the incipient radical cation.Formation of a complex between NO3. and aromatics is likely even in those cases where radical cations are observed, with the assumption that in these cases the complex decomposition rate is greater than 6 * 107 s-1.

Accessing Pincer Bis(carbene) Ni(IV) Complexes from Ni(II) via Halogen and Halogen Surrogates

Martinez, Gabriel Espinosa,Ocampo, Cristian,Park, Yun Ji,Fout, Alison R.

, p. 4290 - 4293 (2016)

This communication describes the two-electron oxidation of (DIPPCCC)NiX (DIPPCCC = bis(diisopropylphenyl-benzimidazol-2-ylidene)phenyl); X = Cl or Br) with halogen and halogen surrogates to form (DIPPCCC)NiX3. These complexes represent a rare oxidation state of nickel, as well as an unprecedented reaction pathway to access these species through Br2 and halogen surrogate (benzyltrimethylammonium tribromide). The NiIV complexes have been characterized by a suite of spectroscopic techniques and can readily reduce to the NiII counterpart, allowing for cycling between the NiII/NiIV oxidation states.

Selective and Mild Deacylation of Hindered Acylarenes with Aqueous Trifluoroacetic Acid

Keumi, Takashi,Morita, Toshio,Inui, Yoko,Teshima, Naomi,Kitajima, Hidehiko

, p. 979 - 980 (1985)

Sterically hindered acylarenes are deacylated to arenes in quantitative yields on heating in boiling 85percent trifluoroacetic acid.Hindered arenecarboxylic acids undergo decarboxylation under the same conditions to give arenes in high yields.

Reactivity of 17-, 18-, and 19-Electron Cationic Complexes Generated by the Electrochemical Oxidation of Tricarbonyl(mesitylene)tungsten

Zhang, Yun,Gosser,Rieger,Sweigart

, p. 4062 - 4068 (1991)

The electrochemical oxidation of (mesitylene)W(CO)3 (W) in MeCN produces the 17-electron complex W+, which reacts very rapidly with solvent (S) or tri-n-butyl phosphite (P) to give 19-electron species (WS+, WP+) that undergo spontaneous further oxidation to the 18-electron analogues (WS2+, WP2+). The identities of WS2+ and WP2+ were established by voltammetric, IR spectroelectrochemical, and NMR experiments. Although the 17-electron ? 19-electron transformation is not directly observable, digital simulation techniques allowed selection of a probable mechanism and semiquantitative determination of the rate and equilibrium parameters describing the interconversion of the 17-, 18-, and 19-electron species: W+ + S ? WS+, k ? 105 M-1 s-1, Keq ? 10-1 M-1; W+ + P ? WP+, k ? 107 M-1 s-1, Keq ? 3 × 103 M-1 at 298 K. The related 18-electron complex WS2+ is quite reactive, but orders of magnitude less so than W+ and WS+. Experiments with (mesitylene)Cr(CO)3 (Cr) suggest that associative attack by MeCN at the 17-electron Cr+ is 104 times slower than attack at the W+ analogue. This study illustrates the power of digital simulation techniques for interpreting complex mechanistic schemes and characterizing important but unobservable reaction intermediates. Electrochemical oxidation of (arene)W(CO)3 occurs without loss of arene or CO ligands, suggesting that the electroactivation of these complexes may have useful synthetic applications; this contrasts sharply with (arene)Cr(CO)3 analogues, which decompose with loss of arene and CO ligands upon oxidation in MeCN.

Grignard reagents in ionic solvents: Electron transfer reactions and evidence for facile Br-Mg exchange

Ramnial, Taramatee,Taylor, Stephanie A.,Clyburne, Jason A. C.,Walsby, Charles J.

, p. 2066 - 2068 (2007)

Grignard reagents form persistent solutions in phosphonium ionic liquids possessing O-donor anions and these solutions are excellent reaction media for electron transfer processes and transmetallation reactions. The Royal Society of Chemistry.

Temperature resolved FTIR spectroscopy of Cr2+/SiO2 catalysts: Acetylene and methylacetylene oligomerisation

Zecchina,Bertarione,Damin,Scarano,Lamberti,Prestipino,Spoto,Bordiga

, p. 4414 - 4417 (2003)

Results related to time-resolved FTIR spectroscopy at variable temperature of acetylene and methylacetylene oligomerization on a model Phillips catalyst were presented. Acetylene and methylacetylene resulted in the immediate formation of benzene and 1,3,5-trimethylbenzene, respectively, without evidence of any measurable intermediate product. This indicated that the active Cr sites were able to coordinate simultaneously three monomers and thus must display a high unsaturative coordination. The results could be an insight of chromium species active in the Phillips catalyst.

Highly active, well-defined (cyclopentadiene)(N-heterocyclic carbene)palladium chloride complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions of aryl chlorides and deboronation homocoupling of arylboronic acids

Jin, Zhong,Guo, Su-Xian,Gu, Xiao-Peng,Qiu, Ling-Ling,Song, Hai-Bing,Fang, Jian-Xin

, p. 1575 - 1585 (2009)

A new class of well-defined N-heterocyclic carbene (NHC)-(cyclopentadiene) palladium chloride complexes such as CpPd(NHC)Cl wasw synthesized from the readily available starting NHC-palladium(II) chloride dimers. These air-stable, coordinatively saturated NHC-Pd complexes bearing the cyclopentadiene (Cp) unit exhibit high catalytic activity in the room temperature Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving unactive aryl chlorides as the substrates. In addition, they are found to be extremely efficient catalysts in the deboronation homocoupling of arylboronic acids at room temperature.

Characterization of the extra-large-pore zeolite UTD-1

Lobo, Raul F.,Tsapatsis, Michael,Freyhardt, Clemens C.,Khodabandeh, Shervin,Wagner, Paul,Chen, Cong-Yan,Balkus Jr., Kenneth J.,Zones, Stacey I.,Davis, Mark E.

, p. 8474 - 8484 (1997)

The molecular sieve UTD-1 is investigated using scanning and transmission electron microscopies (TEM), solid-state NMR spectroscopy, electron (ED) and X-ray diffraction (XRD), adsorption studies, and catalytic test reactions. The results confirm that UTD-1 is the first high-silica zeolite to contain a one;dimensional, extra-large 14-ring pore system. TEM and ED show that UTD-1 is faulted along the (002) planes. Simulations of XRD patterns of faulted structures using DIFFaX indicate that the XRD pattern of a framework containing the so-called double crankshaft chains is in better agreement with the experimental pattern than a framework with the narsarsukite chains previously reported. Thermal/hydrothermal stability studies show that UTD-1 has similar stability to other medium- and large-pore, high-silica zeolites. The ratio of isomerization to disproportionation, and the distribution of trimethylbenzene isomers in the m-xylene isomerization test reaction from UTD-1 are similar to those obtained from other large-pore zeolites (zeolites Y or L). However, UTD-1 shows a p-/o-xylene ratio of products below one.The molecular sieve UTD-1 is investigated using scanning and transmission electron microscopies (TEM), solid-state NMR spectroscopy, electron (ED) and X-ray diffraction (XRD), adsorption studies, and catalytic test reactions. The results confirm that UTD-1 is the first high-silica zeolite to contain a one-dimensional, extra-large 14-ring pore system. TEM and ED show that UTD-1 is faulted along the (002) planes. Simulations of XRD patterns of faulted structures using DIFFaX indicate that the XRD pattern of a framework containing the so-called double crankshaft chains is in better agreement with the experimental pattern than a framework with the narsarsukite chains previously reported. Thermal/hydrothermal stability studies show that UTD-1 has similar stability to other medium-and large-pore, high-silica zeolites. The ratio of isomerization to disproportionation, and the distribution of trimethylbenzene isomers in the m-xylene isomerization test reaction from UTD-1 are similar to those obtained from other large-pore zeolites (zeolites Y or L). However, UTD-1 shows a p-/o-xylene ratio of products below one.

Strategy for Selective Csp2-F and Csp2-Csp2Formations from Organoplatinum Complexes

Sarkissian, Elin,Golbon Haghighi, Mohsen

, p. 1016 - 1020 (2021)

By changing the parameters of fluorination reaction of bisaryl-platinum(II) complexes, each possible competitive pathway of Ar-Ar and Ar-F formation can be selectively controlled. It was discovered that steric hindrance, type of fluorinating reagent, and

Tailoring the Morphology of MTW Zeolite Mesocrystals: Intertwined Classical/Nonclassical Crystallization

Zhao, Yang,Zhang, Hongbin,Wang, Peicheng,Xue, Fangqi,Ye, Zhaoqi,Zhang, Yahong,Tang, Yi

, p. 3387 - 3396 (2017)

The morphology and porosity of zeolite play a significant role in the activity and selectivity of catalytic reactions. It is a dream to optionally modulate zeolite morphology by regulating the crystallization process on the basis of comprehensively understanding the mechanisms. Herein, a series of MTW zeolite mesocrystals can be consciously fabricated with morphologies from a dense structure to a loose one of an oriented nanocrystallite aggregate by changing the H2O/SiO2 ratio. Their intertwined classical/nonclassical crystallization processes are investigated comprehensively. The results indicate that the crystallization of MTW zeolite takes place by a chain of events, including the formation of wormlike particles (WLPs), their aggregation, and crystallization of aggregates. MTW with a loose structure mainly crystallizes by an internal reorganization after a fast aggregation of WLPs in a concentrated system. On the other hand, the dense structure of MTW is realized via the co-occurrence of a coalescence of the participating WLPs during its crystal growth with a slower rate in a dilute system. Moreover, the advantages of MTW with a loose structure are confirmed through cumene cracking and 1,2,4-trimethylbenzene transformation. This method could pave the way for the synthesis of other zeolites with diverse morphologies and/or mesoporosities via subtle regulation of the crystallization pathway.

Promising process for synthesis of 3,5-xylenol from isophorone

Kirichenko,Glazunova,Kirichenko,Dzhemilev

, p. 434 - 438 (2006)

A thermocatalytic process for the synthesis of 3,5-xylenol from isophorone over a silicon dioxide catalyst promoted by iron oxides was developed. The process holds promise for commercialization. Nauka/Interperiodica 2006.

Hastings,Nicholson

, p. 730,734 (1957)

Eichhorn, Bryan W.,Haushalter, Robert C.,Pennington, William T.

, p. 8704 - 8706 (1988)

Product Ratios Dependent on and Independent of the Left Group in a Single Series: Potassium Metal Provoked Reactions of Aryl Halides with Amide and Acetone Enolate Ions That Occur during Mixing

Tremelling, Michael J.,Bunnett, J. F.

, p. 7375 - 7377 (1980)

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A new peroxo-route for the synthesis of Mg-Zr mixed oxides catalysts: Application in the gas phase acetone self-condensation

Krivtsov, Igor,Faba, Laura,Díaz, Eva,Ordó?ez, Salvador,Avdin, Viacheslav,Khainakov, Sergei,Garcia, Jose R.

, p. 26 - 33 (2014)

We propose in this manuscript a new peroxo-mediated procedure for preparing magnesia-zirconia mixed oxides, with Mg/Zr molar ratio between 1 and 3, with enhanced distribution of basic sites. The mixed magnesia-zirconia oxides have been prepared from the gelled complex by Pechini-type method. The MgO-ZrO 2 materials have been characterized and used as catalysts for acetone aldol condensation. The proposed preparation method provides a high degree of molecular homogeneity and favours the formation of magnesia-stabilized zirconia phase. Acetone gas-phase self-condensation was carried out over these catalysts as model reaction requiring the presence of basic sites. The condensation yields diacetone alcohol and mesityl oxide as mean C6 products, and phorones, isophorones and mesitylene as C9 products. In comparison to Mg-Zr oxide prepared by co-precipitation, these new materials present better conversions and higher selectivity to linear dimers and trimers (as mesitylene), whereas the selectivity for isophorones is significantly lower.

Relative Reactivities of Amide, Diphenylphosphide, and Diphenylarsenide Ions toward Aryl Radicals

Alonso, Ruben A.,Bardon, Alicia,Rossi, Roberto A.

, p. 3584 - 3587 (1984)

Competition experiments have been carried out in liquid ammonia at reflux temperature to determine the relative rate constants for the coupling reactions of amide (NH2-), diphenylphosphide (Ph2P-), and diphenylarsenide (Ph2As-) toward aryl radicals.It is proposed that these nucleophiles react under photostimulation with halo aromatic substrates through an SRN1 mechanism of aromatic substitution.Relative rate constants of NH2- vs.Ph2P- ions toward 2,4,6-trimethylphenyl radicals and Ph2P- vs.Ph2As- ios toward 2-quinolyl radicals have been determined.The results here reported indicate that NH2- (1.00) - (6.4) = Ph2As- (6.4).The fact that there is not a difference in the rate constants of Ph2P- vs.Ph2As- suggests that both nucleophiles react at diffusion-controlled rate.In competition experiments of Ph2P- vs.Ph2As- ions toward phenyl radicals, it was found that Ph2P- (1.00) > Ph2As- (0.44).The decrease of the Ph2As- ion reactivity is attributed to the reversible coupling of this nucleophile with phenyl radicals.

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Sucharda,Kuczynski

, (1935)

-

-

Tsutsui, M.,Zeiss, H.

, p. 1367 - 1369 (1959)

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A new method to prepare functional phosphines through steady-state photolysis of triarylphosphines

Yasui, Shinro,Ando, Taro,Ozaki, Masashi,Ogawa, Yuya,Shioji, Kosei

, (2018)

The steady-state photolysis of triarylphosphine, Ar3P, was carried out using a xenon lamp or a high-pressure mercury lamp under an argon atmosphere in a solvent containing a functional group, CH3X. Gas chromatograph-mass spectroscopic analysis on the photolysis showed that a phosphine to which the functional group from the solvent is incorporated, Ar2PCH2X, was formed in a moderate yield, along with tetraaryldiphosphine, Ar2PPAr2. The product, Ar2PCH2CN, from the photolysis in acetonitrile (X=CN) was isolated by column chromatography. In the photolysis in other solvents tried here (ethyl acetate, acetone, 2-butanone, and 3,3-dimethyl-2-butanone), Ar2PCH2X formed in the reaction mixture was so labile on a silica-gel column that it was treated with S8 powder to convert to the corresponding phosphine sulfide, Ar2P(=S)CH2X. The resulting phosphine sulfide was isolated by column chromatography. The isolated products in these reactions, Ar2PCH2CN and Ar2P(=S)CH2X, were characterized by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and elemental analysis or high-resolution mass spectroscopy. The formation of Ar2PCH2X as well as Ar2PPAr2 is explained by homolytic cleavage of a P-C bond of Ar3P in the photoexcited state. This reactivity of Ar3P in the photoexcited state is in sharp contrast to that exerted under aerobic conditions, where Ar3P in the photoexcited state donates readily an electron to oxygen producing the radical cation, Ar3P·+. This photoreaction, which affords a functional phosphine, Ar2PCH2X, in one-pot with generating very small amounts of unidentified side products, has potential for use in preparing functional phosphines.

Infrared and Raman spectra, ab initio calculations and conformational studies of ethyl iodosilane

Aleksa, Valdemaras,Powell, David L.,Gruodis, Alytis,Hassler, Karl,Hummeltenberg, Reinhard,Herzog, Klaus,Salzer, Reiner,Klaeboe, Peter,Nielsen, Claus J.

, p. 105 - 118 (2003)

Ethyl iodosilane (CH3CH2-SiH2I) was synthesized for the first time. Infrared spectra were recorded in the vapour, amorphous and crystalline solid phases in MIR and FIR regions. Additional MIR spectra of the compound isolated in argon and nitrogen matrices were obtained at 5 K. Raman spectra of the liquid, excited by argon and by Nd3+ YAG lasers, were recorded at room temperature including polarization measurements. The spectra were studied in an extended temperature range 173-353 K and a ΔH value of 1.2 ± 0.3 kJ mol-1 was obtained with gauche being the low energy conformer. Spectra of the amorphous and crystalline solids were obtained at liquid nitrogen temperature. Ethyl iodosilane exists in an equilibrium between anti and gauche conformers, in the vapour, liquid and amorphous states. After careful annealing the amorphous solid on a cold Cu finger (Raman) or on a CsI or Si window (infrared) to 160 K a partly crystalline solid was formed. A number of IR and Raman bands were reduced in intensity after annealing, although they did not vanish completely. From comparison between the observed and calculated vibrational modes it was apparent that the gauche conformer was present in the crystal. The sample was mixed with argon and nitrogen in a ratio 1:1000, deposited on a window at 5 or 10 K and annealed to temperatures between 5 and 36 K (argon) and 5-30 K (nitrogen). IR bands attributed to the anti and gauche conformers were reduced and increased in intensities, respectively. Thus, the gauche conformer was the low energy conformer in the matrices and probably also in the vapour phase. Ab initio calculations were performed at the RHF/3-21 G* and 6-311G* B3LYPs and gave optimized geometries, IR and Raman intensities and vibrational frequencies for the anti and gauche conformers. An enthalpy difference of 0.9 kJ mol-1 was obtained from the calculations with gauche being the low energy conformer. After scaling, a reasonably good agreement between the experimental and calculated wavenumbers for the anti and gauche conformer was obtained. The spectra of ethyl iodosilane were closely related to those of the corresponding ethyl fluoro, ethyl chloro and ethyl bromosilane.

Perfluoroalkylated Main-Group Element Lewis Acids as Catalysts in Transfer Hydrogenation

Bader, Julia,Maier, Alexander F. G.,Paradies, Jan,Hoge, Berthold

, p. 3053 - 3056 (2017)

Transfer hydrogenation plays an important part in organic chemistry. Recently, strong Lewis acids like B(C6F5)3 have been introduced as a catalyst for these reactions. We successfully employed the Lewis acid (C2F5)3PF2 as a catalyst in the transfer hydrogenation between 1,3,5-trimethylcyclohexa-1,4-diene and 1,1-diphenylethylene. Surprisingly, the treatment of the diene alone with a catalytic amount of (C2F5)3PF2 led to a quantitative dismutation to mesitylene and 1,3,5-trimethylcyclohexane. With B(C6F5)3, there was a solvent-dependency: in CH2Cl2 mainly the dismutation products were obtained, while in toluene the evolution of H2 was observed. Additionally, the catalytic activity of various perfluoroalkylated germanes and silanes was tested.

Phosphoric acid-modified commercial kieselguhr supported palladium nanoparticles as efficient catalysts for low-temperature hydrodeoxygenation of lignin derivatives in water

Cui, Yuntong,Liu, Zhaohui,Ran, Jiansu,Wang, Jianjian,Yangcheng, Ruixue

, p. 1570 - 1577 (2022/03/14)

Efficient production of high value-added chemicals and biofuels via low-temperature chemoselective HDO of lignin derivatives in water is still a challenge. Here, we construct a low-cost, active and stable Pd/PCE catalyst using phosphoric acid-modified commercial Celite (PCE) as the support, and this catalyst exhibits excellent activity in low-temperature HDO of vanillin as well as other lignin derivatives in water. The superior catalytic performance is due to the presence of P species on the surface of Pd/PCE, accelerating the selective conversion of the intermediate into the final product. Detailed experimental and mechanistic studies reveal that the rapid conversion of the intermediate to the final product proceeds via a free-radical process in an interfacial microenvironment created by intimate interacting between the P species and Pd NPs. The insights of this work provide a new low-cost catalytic system for efficient production of valuable chemicals and future biofuels from lignin derivatives. This journal is

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

Shi, Jiale,Yuan, Tao,Zheng, Meifang,Wang, Xinchen

, p. 3040 - 3047 (2021/03/09)

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Shon, Jong-Hwa,Kim, Dooyoung,Rathnayake, Manjula D.,Sittel, Steven,Weaver, Jimmie,Teets, Thomas S.

, p. 4069 - 4078 (2021/04/06)

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

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