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100-66-3

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100-66-3 Usage

Chemical Description

Different sources of media describe the Chemical Description of 100-66-3 differently. You can refer to the following data:
1. Anisole is a colorless liquid used as a solvent and flavoring agent.
2. Anisole is an electron-rich aromatic compound used as a substrate in the amination reaction.
3. Anisole is a colorless liquid with a pleasant odor.

Product Features

Anisole, also known as anise ether, methoxybenzene methyl phenyl ether, is a colorless liquid with an odor of anise, sweet, naturally present in the tarragon oil, insoluble in water, soluble in alcohol, ether, acetone, soluble in benzene. It irritates the eyes and mucous membranes. It is obtained originally from distilled methyl salicylate or methoxybenzoate, is now mainly produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Anisole is prone to start Electrophilic substitution reaction in aromatic nucleus, and condensed with formaldehyde to produce viscous oil or resin material, reacts with phosphorus trichloride to produce chlorine anisole and a small amount of o-chloro product, reacts with thionyl chloride to produce 2,4,6-trichloroanisole. In addition, anisole is heated to react with hydrobromic or hydroiodic, carbon-oxygen bond cleaves, phenol and halogenated methane is produced, which is an important method for determining methoxy group of benzene ring. The above information is edited by the lookchem of Yan Yanyong.

Chemical properties

It is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.

Uses

Different sources of media describe the Uses of 100-66-3 differently. You can refer to the following data:
1. 1. Anisole is a solvent used in the synthesis of organic compounds and in large-scale applications such as the production of perfumes.2. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.3. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.4. Anisole has been used directly in the synthesis of the marine pyrrole alkaloids polycitone A and B and the nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol.5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.
2. Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.

Toxicity

Anisole has acute toxicity, LD50: 3700mg/kg (oral in rats); 2800mg/kg (oral in mice). Rabbit percutaneous: 500mg (24h), moderate stimulation. Anisole is also mutagenic, causing DNA inhibition, 25 μmol/L in human lymphocytes.

Production method

Anisole is produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Phenol was mixed with sodium hydroxide solution, dimethyl sulfate was slowly added at below 10°C. And then heat to 40 °C, reflux for 18h, then stand for separation of the oil and dried with anhydrous calcium chloride, vacuum distillation to obtain anisole. It is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react. It is generated from heating phenol and methanol. It is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.

Limited use

FEMA (mg/kg): Soft drinks 9.0, cold 16, confectionery51, bakery 34. limited in moderation (FDA§172.515,2000).

Chemical Properties

Anisole is a colorless to yellowish liquid with a characteristic pleasant, anise-like, agreeable, aromatic, spicy-sweet odor. It is used in perfumery.

Occurrence

Anisole is a natural product found in apple juice and in the oil of Artemisia dracunculus var. turkestanica; also reported found in butter, Camembert cheese, roasted beef, olive (Olea europae), Malay apple, Jerusalem artichoke (Helianthus tuberosus), Bourbon vanilla, truffles, crab and sopadilla fruit (Achras sapota L.).

Application

Anisole is an organic compound with the chemical formula C7H8O with a pleasant anise-like aroma, used in organic synthesis and also as a solvent, fragrance and insect repellent. For organic synthesis, it is also used as solvent, fragrance and insect repellent.

Preparation

Anisole is synthesized by reacting phenol and dimethyl sulfate in the presence of aqueous NaOH; by passing methyl chloride into a suspension of sodium phenolate in liquid ammonia.

Definition

ChEBI: Anisole is a monomethoxybenzene that is benzene substituted by a methoxy group. It has a role as a plant metabolite.

Aroma threshold values

Detection: 50 ppb

Synthesis Reference(s)

Canadian Journal of Chemistry, 40, p. 441, 1962 DOI: 10.1139/v62-070Journal of the American Chemical Society, 88, p. 4271, 1966 DOI: 10.1021/ja00970a037Organic Syntheses, Coll. Vol. 1, p. 58, 1941

General Description

A clear straw-colored liquid with an aromatic odor. Insoluble in water and the same density as water. Vapors heavier than air. Flash point 125°F. Boiling point 307°F. Moderately toxic by ingestion. A skin irritant. Used to make perfumes, flavorings and as a solvent.

Air & Water Reactions

Flammable. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Insoluble in water

Reactivity Profile

Ethers, such as Anisole can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Health Hazard

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

Safety Profile

Moderately toxic by ingestion and inhalation. A skin irritant. A flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid fumes.

Potential Exposure

Anisole is used as a solvent; a flavoring, vermicide, making perfumes; and in organic synthesis.

Purification Methods

Shake anisole with half its volume of 2M NaOH, and the emulsion is allowed to separate. Repeat three times, then wash twice with water, dry over CaCl2, filter, dry over sodium wire and finally distil it from fresh sodium under N2 using a Dean-Stark trap (samples in the trap being rejected until free from turbidity) [Caldin et al. J Chem Soc, Faraday Trans 1 72 1856 1976]. Alternatively dry it with CaSO4 or CaCl2, or by refluxing with sodium or BaO with crystalline FeSO4 or by passage through an alumina column. Traces of phenols are removed by prior shaking with 2M NaOH, followed by washing with water. It has been be purified by zone refining. [Beilstein 6 IV 548.]

Incompatibilities

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 100-66-3 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 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 100-66:
(5*1)+(4*0)+(3*0)+(2*6)+(1*6)=23
23 % 10 = 3
So 100-66-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

100-66-3 Well-known Company Product Price

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

  • (A0492)  Anisole  >99.0%(GC)

  • 100-66-3

  • 25g

  • 105.00CNY

  • Detail
  • TCI America

  • (A0492)  Anisole  >99.0%(GC)

  • 100-66-3

  • 500g

  • 400.00CNY

  • Detail
  • Alfa Aesar

  • (A12997)  Anisole, 99%   

  • 100-66-3

  • 500g

  • 377.0CNY

  • Detail
  • Alfa Aesar

  • (A12997)  Anisole, 99%   

  • 100-66-3

  • 2500g

  • 1376.0CNY

  • Detail
  • Alfa Aesar

  • (A12997)  Anisole, 99%   

  • 100-66-3

  • 10000g

  • 2213.0CNY

  • Detail
  • Sigma-Aldrich

  • (296295)  Anisole  anhydrous, 99.7%

  • 100-66-3

  • 296295-100ML

  • 1,060.02CNY

  • Detail
  • Sigma-Aldrich

  • (296295)  Anisole  anhydrous, 99.7%

  • 100-66-3

  • 296295-1L

  • 1,432.08CNY

  • Detail
  • Sigma-Aldrich

  • (296295)  Anisole  anhydrous, 99.7%

  • 100-66-3

  • 296295-2L

  • 2,021.76CNY

  • Detail
  • Sigma-Aldrich

  • (123226)  Anisole  ReagentPlus®, 99%

  • 100-66-3

  • 123226-250ML

  • 691.47CNY

  • Detail
  • Sigma-Aldrich

  • (123226)  Anisole  ReagentPlus®, 99%

  • 100-66-3

  • 123226-1L

  • 1,432.08CNY

  • Detail
  • Sigma-Aldrich

  • (123226)  Anisole  ReagentPlus®, 99%

  • 100-66-3

  • 123226-2.5L

  • 2,183.22CNY

  • Detail
  • Sigma-Aldrich

  • (123226)  Anisole  ReagentPlus®, 99%

  • 100-66-3

  • 123226-18L-CS

  • 12,273.30CNY

  • Detail

100-66-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name anisole

1.2 Other means of identification

Product number -
Other names Anizol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:100-66-3 SDS

100-66-3Synthetic route

methyl iodide
74-88-4

methyl iodide

phenol
108-95-2

phenol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium hydroxide; acyclic polyethylene oxides In dichloromethane; water for 0.5h;100%
With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide for 1h; Product distribution; Ambient temperature; other phenols and alcohols, other alkylating agents, other reagents and solvents, var. time;100%
With potassium hydroxide; Aliquat 336 at 20℃; for 5h;99%
5-(2-methoxy-phenoxy)-1-phenyl-1H-tetrazole
17743-22-5

5-(2-methoxy-phenoxy)-1-phenyl-1H-tetrazole

A

1-phenyl-5-hydroxytetrazole
5097-82-5

1-phenyl-5-hydroxytetrazole

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With hydrazine hydrate; palladium on activated charcoal In ethanol; water; benzene for 1.83333h; Ambient temperature;A n/a
B 100%
palladium on activated charcoal In ethanol; benzene Mechanism; Product distribution; various reagents, temperatures and reaction times;
With sodium hypophosphite; palladium on activated charcoal In ethanol; benzene at 80℃; Relative steady-state rates, relative extrapolated intercepts;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With hydrogen In methanol at 70℃; under 750.075 Torr; for 0.333333h;100%
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;98%
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -58℃; for 0.000861111h;
Stage #2: With methanol In tetrahydrofuran; hexane at -58℃; for 0.000436111h;
92%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetraphenyldisilane; cesium fluoride In acetonitrile at 100℃; for 0.0833333h;100%
With tetrakis(triphenylphosphine) palladium(0); formaldehyd; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;85%
With N,N,N,N,-tetramethylethylenediamine; C39H46IrN4 In acetonitrile at 45℃; for 48h; Sealed tube; Glovebox; Inert atmosphere;80%
para-iodoanisole
696-62-8

para-iodoanisole

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With lithium aluminium tetrahydride; di-tert-butyl peroxide In tetrahydrofuran for 1.5h; Irradiation;100%
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;96%
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;95%
1-methoxycyclohexa-1,4-diene
2886-59-1

1-methoxycyclohexa-1,4-diene

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 25℃; for 1h;100%
In acetone at 0℃; for 1h;90%
With manganese(IV) oxide In methyl cyclohexane at 70℃; for 16h;43%
With tris(1,10-phenantholine)iron(III) perchlorate In acetonitrile at -30℃; Rate constant; other reagent;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

phenol
108-95-2

phenol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
N,N,N',N'-tetrabutyl-N''-methylguanidine at 160℃; for 4.5h;100%
N,N,N',N'-tetrabutyl-N''-methylguanidine at 160℃; for 4.5h; Product distribution; other catalysts, other reaction conditions, other phenols;100%
With tetrabutylammomium bromide; potassium carbonate at 93℃; for 5h;99%
potassium phenolate
100-67-4

potassium phenolate

methyl iodide
74-88-4

methyl iodide

A

methoxybenzene
100-66-3

methoxybenzene

B

KI

KI

Conditions
ConditionsYield
acyclic polyethylene oxides In benzene at 25℃;A 100%
B n/a
4-methoxyphenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-45-3

4-methoxyphenyl(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

para-iodoanisole
696-62-8

para-iodoanisole

D

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaCl, water and chloroform was vigorously stirred under reflux at 56°C, 2-2.5 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 0%
B 100%
C 100%
D 0%
2-bromoanisole
578-57-4

2-bromoanisole

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); formaldehyd; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;99%
With butyl magnesium bromide; zirconocene dichloride for 12h; Ambient temperature;98%
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction;98%
4-iodoanisol
529-28-2

4-iodoanisol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With triethylamine In water at 25℃; for 1h; UV-irradiation;99%
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;98%
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;95%
4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With lithium borohydride; C22H19F3N4NiO2S In tetrahydrofuran at 70℃; for 24h; Reagent/catalyst;99%
With lithium borohydride; C30H21F6N2NiO2P In tetrahydrofuran at 70℃; for 3h; Reagent/catalyst; Concentration; Temperature; Time; Schlenk technique; Inert atmosphere;89%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethyl-cyclohexane at 130℃; for 15h; Inert atmosphere;74%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 130℃; for 15h; Inert atmosphere;74 %Chromat.
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 140℃; for 8h; Inert atmosphere;30 %Chromat.
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With ammonium formate In water at 20℃; for 3h;98%
With isopropyl alcohol; sodium hydroxide at 24.84℃; under 760.051 Torr; for 1h; Inert atmosphere; UV-irradiation;97%
With palladium on ceria; sodium hydroxide In isopropyl alcohol at 40℃; for 18h; Irradiation; Inert atmosphere; Sealed tube;94%
3-(4-methoxyphenoxy)-1,2-benzisothiazole 1,1-dioxide
132636-68-1

3-(4-methoxyphenoxy)-1,2-benzisothiazole 1,1-dioxide

A

methoxybenzene
100-66-3

methoxybenzene

B

saccharin
81-07-2

saccharin

Conditions
ConditionsYield
With sodium hypophosphite; palladium on activated charcoal In water; benzene for 3h; Heating;A 98%
B n/a
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

A

3,3'-dimethoxybiphenyl
6161-50-8

3,3'-dimethoxybiphenyl

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 36h; Inert atmosphere;A 1%
B 98%
With 18-crown-6 ether; zinc; 10 percent Pd/C In water; acetone at 20℃; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Ullmann coupling;
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

isopropyl alcohol
67-63-0

isopropyl alcohol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With sodium hydroxide at 24.84℃; under 760.051 Torr; for 5h; Inert atmosphere; UV-irradiation; Sealed tube;98%
dimethyl 2-oxo-1,3-propanedisulfonate
689-16-7

dimethyl 2-oxo-1,3-propanedisulfonate

phenol
108-95-2

phenol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With sodium hydroxide at 40℃; for 6h; also diethyl 2-oxo-1,3-propanedisulfonate; var. reaction time; other alkylating agents;97.2%
dimethyl sulfate
77-78-1

dimethyl sulfate

phenol
108-95-2

phenol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane for 1.5h;97%
With potassium carbonate In acetone for 0.0833333h; Etherification; methylation; microwave irradiation;92%
With sodium hydroxide; N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In 1,2-dichloro-ethane for 6h; Heating;85%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

A

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With water; triphenylphosphine; sodium iodide; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 2h; Rate constant; Product distribution; Mechanism; var. organic halides; other solvent; var. temp., and reaction times;A 2.5%
B 96.8%
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Ullmann Condensation; Inert atmosphere;A 92%
B 6%
With NaH-t-AmONa-Ni(OAc)2-bpy In tetrahydrofuran at 63℃; for 8h;A 73%
B 16 % Chromat.
1-(4-Methoxyphenyl)-3,3-diethyl-1-triazene
36719-69-4

1-(4-Methoxyphenyl)-3,3-diethyl-1-triazene

A

para-iodoanisole
696-62-8

para-iodoanisole

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With cation exchange resin BioRad AG 50W-X12 (H+); sodium iodide In acetonitrile at 75℃; Product distribution; further solvent: THF, DMSO;A 96%
B 4%
Methyl trichloroacetate
598-99-2

Methyl trichloroacetate

phenol
108-95-2

phenol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate at 150℃; for 2h;96%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;96%
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;85%
With isopropyl alcohol at 20℃; for 18h; UV-irradiation; chemoselective reaction;78%
2-Nitroanisole
91-23-6

2-Nitroanisole

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium phosphate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium(II) acetylacetonate; isopropyl alcohol In 1,4-dioxane at 130℃; for 4h; Time; Reagent/catalyst; Solvent; Inert atmosphere;96%
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; isopropyl alcohol In 1,4-dioxane at 130℃; for 4h;96 %Chromat.
triethyl(4-methoxyphenyl)germane

triethyl(4-methoxyphenyl)germane

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) In 1,4-dioxane at 20℃;96%
2-methoxyphenethyl alcohol
7417-18-7

2-methoxyphenethyl alcohol

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Autoclave; Green chemistry;96%
methanol
67-56-1

methanol

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

A

dimethyl phenylphosphonite
18351-42-3

dimethyl phenylphosphonite

B

diphenyl methylphosphonate
7526-26-3

diphenyl methylphosphonate

C

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
Stage #1: phosphorus trichloride; phenol at 65 - 250℃; for 4h;
Stage #2: methanol at 204 - 260℃; for 2h; Product distribution / selectivity;
A n/a
B 95.6%
C n/a
Stage #1: phosphorus trichloride; phenol at 65 - 250℃; for 4h;
Stage #2: methanol; methyl iodide at 210 - 250℃; Product distribution / selectivity;
A 7.14%
B 92.86%
C n/a
bromobenzene
108-86-1

bromobenzene

sodium methylate
124-41-4

sodium methylate

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
copper(I) bromide In methanol; N,N-dimethyl-formamide at 110℃; for 0.75h;95%
copper(I) bromide In methanol for 6h; Product distribution; Mechanism; Rate constant; Heating; by investigating the influence of several reaction parameters (the nature and concentration of the copper catalyst, the cosolvents, the concentration and number of equivalents of the nucleophile, the bromide concentration, the aryl bromide subst. effect;95%
With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Reagent/catalyst; Autoclave; Green chemistry;80%
With hemicucurbituril supported [Bmim]Cl In toluene for 9h; Reflux;78%
With ethyl acetate; copper(I) bromide In methanol for 2h; Heating; Yield given;
Methyl formate
107-31-3

Methyl formate

para-iodoanisole
696-62-8

para-iodoanisole

sodium methylate
124-41-4

sodium methylate

A

methyl 4-methoxybenzoate
121-98-2

methyl 4-methoxybenzoate

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 40℃; under 11250.9 Torr; for 7h;A 95%
B 5%
methyl phenyl carbonate
13509-27-8

methyl phenyl carbonate

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
dmap at 130℃; for 2h; other catalysts;95%
N,N,N',N'-tetrabutyl-N''-methylguanidine at 110℃; for 1h; Product distribution; other catalysts, other reaction conditions, other aryl methyl carbonates;93 % Chromat.
dodecyl-dimethylsulphonium iodide
18412-81-2

dodecyl-dimethylsulphonium iodide

phenol
108-95-2

phenol

A

S-methyl-L-cysteine
1187-84-4

S-methyl-L-cysteine

B

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium hydroxide In water at 70℃; for 5h; pH = 9;A n/a
B 95%
propionyl chloride
79-03-8

propionyl chloride

methoxybenzene
100-66-3

methoxybenzene

4-Methoxypropiophenone
121-97-1

4-Methoxypropiophenone

Conditions
ConditionsYield
With Noccaea caerulescens extract supported in montmorillonite K10 at 60℃; for 6h; Friedel Crafts acylation; Inert atmosphere; regioselective reaction;100%
With aluminum (III) chloride In dichloromethane at 5 - 20℃; for 2.5h;98%
With benzyltributylammonium tetrachloroferrate at 50℃; for 0.1h; Friedel-Crafts reaction;93%
acetic anhydride
108-24-7

acetic anhydride

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With polystyrene-bound tetrafluorophenylbis(triflyl)methane In nitromethane at 50℃; for 2h; Friedel-Crafts acylation;100%
With lithium perchlorate at 60℃; for 1h;100%
With Sulfate; zirconium(IV) oxide at 110℃;100%
2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

methoxybenzene
100-66-3

methoxybenzene

4-methoxyisobutyrophenone
2040-20-2

4-methoxyisobutyrophenone

Conditions
ConditionsYield
With hafnium(IV) trifluoromethanesulfonate; lithium perchlorate In nitromethane for 6h; Ambient temperature;100%
With lithium perchlorate at 60℃; for 1.5h;99%
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Ambient temperature;90%
acetic acid
64-19-7

acetic acid

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: acetic acid; methoxybenzene With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;
Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h;
100%
With methanesulfonic acid; pyrographite at 80℃; for 0.333333h; Friedel-Crafts acylation;98%
With aluminum oxide; trifluoroacetic anhydride for 0.166667h; Ambient temperature;96%
n-valeryl chloride
638-29-9

n-valeryl chloride

methoxybenzene
100-66-3

methoxybenzene

p-Methoxyvalerophenon
1671-76-7

p-Methoxyvalerophenon

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 15h; Ambient temperature;100%
(p-MeOC6H4)2BSbCl6 In dichloromethane for 24h; Ambient temperature;88%
With aluminium trichloride In tetrachloromethane at 0℃; for 2h;87%
2-Phenylbutyryl chloride
36854-57-6

2-Phenylbutyryl chloride

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)-2-phenylbutan-1-one
78423-10-6

1-(4-methoxyphenyl)-2-phenylbutan-1-one

Conditions
ConditionsYield
aluminum (III) chloride at 0 - 20℃; for 2h; Friedel Crafts Acylation;100%
Stage #1: 2-Phenylbutyryl chloride; methoxybenzene With aluminum (III) chloride In carbon disulfide at 10 - 20℃; for 20h; Inert atmosphere; Cooling with ice;
Stage #2: With water In carbon disulfide
94%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2.5h; Friedel-Crafts Acylation;76%
methoxybenzene
100-66-3

methoxybenzene

benzoic acid anhydride
93-97-0

benzoic acid anhydride

4-Methoxybenzophenone
611-94-9

4-Methoxybenzophenone

Conditions
ConditionsYield
With gallium(III) trichloride; silver hexafluoroantimonate In 1,2-dichloro-ethane for 7h; Heating;100%
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;98%
With lithium perchlorate In nitromethane at 100℃; for 4h;97%
methoxybenzene
100-66-3

methoxybenzene

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromo-4'-methoxybenzophenone
54118-75-1

4-bromo-4'-methoxybenzophenone

Conditions
ConditionsYield
aluminum (III) chloride In dichloromethane at 5 - 20℃; for 3h; Friedel Crafts Acylation;100%
With aluminum (III) chloride In dichloromethane at 0℃; for 3h;99%
With aluminum (III) chloride In dichloromethane for 3h;99%
methoxybenzene
100-66-3

methoxybenzene

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 3.5h; Heating;100%
With Selectfluor; sodium bromide In acetonitrile at 20℃; for 21h;100%
With bis[1-methyl-3-(3-sulfopropyl)imidazolium] hexafluorotitanate; dihydrogen peroxide; sodium bromide In water at 25℃; for 3h; Reagent/catalyst; Concentration; Solvent; Temperature; Green chemistry;100%
methoxybenzene
100-66-3

methoxybenzene

2-methoxycyclohexane
931-56-6

2-methoxycyclohexane

Conditions
ConditionsYield
With hydrogen; [(norbornadiene)rhodium(I)chloride]2; phosphinated polydiacetylene In n-heptane at 30℃; under 60800 Torr; for 0.7h;100%
With hydrogen; Rh on carbon In methanol at 20℃; under 760.051 Torr; for 1h;100%
With hydrogen In hexane at 24.84℃; under 750.075 Torr; for 3h;100%
methoxybenzene
100-66-3

methoxybenzene

para-iodoanisole
696-62-8

para-iodoanisole

Conditions
ConditionsYield
With IPy2BF4*2HBF4 In dichloromethane for 0.25h; Ambient temperature;100%
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;100%
With ammonium iodide; 3-chloro-benzenecarboperoxoic acid for 2h;100%
1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)adamantane
726-94-3

1-(4-methoxyphenyl)adamantane

Conditions
ConditionsYield
With molybdenum hexacarbonyl Sealed tube; regioselective reaction;100%
With potassium carbonate; palladium on activated charcoal at 120℃; for 12h;91%
With palladium 10% on activated carbon; potassium carbonate for 20h; Heating;82.65%
trimethylsilyl cyclohexanecarboxylate
69435-89-8

trimethylsilyl cyclohexanecarboxylate

methoxybenzene
100-66-3

methoxybenzene

cyclohexyl 4-methoxyphenyl ketone
7469-80-9

cyclohexyl 4-methoxyphenyl ketone

Conditions
ConditionsYield
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 25h; Ambient temperature;100%
trimethylsilyl ester of hydrocinnamic acid
21273-15-4

trimethylsilyl ester of hydrocinnamic acid

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)-3-phenylpropan-1-one
5739-38-8

1-(4-methoxyphenyl)-3-phenylpropan-1-one

Conditions
ConditionsYield
With SiClO4; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 63h; Ambient temperature;100%
methoxybenzene
100-66-3

methoxybenzene

1-(2,3,4,5,6-pentamethylphenyl)butan-1-one
84858-88-8

1-(2,3,4,5,6-pentamethylphenyl)butan-1-one

A

1-(2-methoxyphenyl)butan-1-one
13404-83-6

1-(2-methoxyphenyl)butan-1-one

B

pentamethylbenzene,
700-12-9

pentamethylbenzene,

C

1-(4-methoxyphenyl)-1-butanone
4160-51-4

1-(4-methoxyphenyl)-1-butanone

Conditions
ConditionsYield
trifluoroacetic acid for 5h; Heating;A n/a
B 100%
C n/a
methoxybenzene
100-66-3

methoxybenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

1-methoxy-4-(phenylsulfanyl)benzene
5633-57-8

1-methoxy-4-(phenylsulfanyl)benzene

Conditions
ConditionsYield
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Heating;100%
With dipotassium peroxodisulfate In trifluoroacetic acid at 20℃; for 16h;89%
Stage #1: diphenyldisulfane With thionyl chloride In 1,2-dichloro-ethane at 5 - 30℃; for 4h;
Stage #2: With aluminum (III) chloride In 1,2-dichloro-ethane at 5 - 10℃; for 1h;
Stage #3: methoxybenzene In 1,2-dichloro-ethane for 4h;
88.5%
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Product distribution; Heating; effect of Lewis acid and silver salt;
methoxybenzene
100-66-3

methoxybenzene

N,N-diacetyl-p-nitrophenylsulphenamide
79562-11-1

N,N-diacetyl-p-nitrophenylsulphenamide

A

4-(4-methoxyphenylsulfanyl)nitrobenzene
22865-50-5

4-(4-methoxyphenylsulfanyl)nitrobenzene

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With trifluoroacetic acid at 190 - 200℃;A 100%
B 21%
methoxybenzene
100-66-3

methoxybenzene

phenol
108-95-2

phenol

Conditions
ConditionsYield
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.3h; Heating;100%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 5h; Catalytic behavior;96%
With monochloroborane dimethyl sulfide complex In benzene Heating;95%
2,5-dichloro-2,5-dimethyl hexane
6223-78-5

2,5-dichloro-2,5-dimethyl hexane

methoxybenzene
100-66-3

methoxybenzene

1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-methoxynaphthalene
51510-70-4

1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-methoxynaphthalene

Conditions
ConditionsYield
aluminum (III) chloride at 0℃; for 2h;100%
With aluminium trichloride 1.) RT, 30 min, 2.) reflux, 15 min;86%
With aluminium trichloride Heating;
methoxybenzene
100-66-3

methoxybenzene

4-methoxynitrosobenzene
1516-21-8

4-methoxynitrosobenzene

Conditions
ConditionsYield
With nitric oxide; trifluoroacetic anhydride for 0.133333h; Product distribution; Ambient temperature;100%
With hydrogenchloride; 1-(4-(nitrosooxy)butyl)-3-methylimidazolium chloride In water at 0 - 5℃; for 1.08333h; regioselective reaction;88%
With nitrosonium tetrafluoroborate In acetonitrile at 25℃; for 0.5h;87%
5-bromovaleroyl chloride
4509-90-4

5-bromovaleroyl chloride

methoxybenzene
100-66-3

methoxybenzene

5-bromo-1-(4-methoxyphenyl)pentan-1-one
69287-12-3

5-bromo-1-(4-methoxyphenyl)pentan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h;100%
With aluminium trichloride Friedel-Crafts acylation;85%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h; Friedel-Crafts Acylation;
With metallic chloride at 50℃; Friedel-Crafts Acylation;
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Inert atmosphere;
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

methoxybenzene
100-66-3

methoxybenzene

1,1-diphenyl-3-(trimethylsilyl)-1-(trimethylsilyloxy)prop-2-yne
350693-36-6

1,1-diphenyl-3-(trimethylsilyl)-1-(trimethylsilyloxy)prop-2-yne

(1-(4-methoxyphenyl)-3,3-diphenylpropa-1,2-dien-1-yl)trimethylsilane

(1-(4-methoxyphenyl)-3,3-diphenylpropa-1,2-dien-1-yl)trimethylsilane

Conditions
ConditionsYield
In dichloromethane at -78℃; for 3h; Friedel-Crafts reaction;100%

100-66-3Related news

A study of the hydrodeoxygenation of Anisole (cas 100-66-3) over Re-MoOx/TiO2 catalyst07/26/2019

A well-characterized Re-MoOx/TiO2 catalyst was used to investigate the reaction sequence involved during the hydrodeoxygenation of anisole in a batch reactor by varying the initial anisole concentration in the reactant mixture (0.182–0.382 mol L−1 corresponding to 2.6–5.4 wt.%), the reaction t...detailed

Flame structure of laminar premixed Anisole (cas 100-66-3) flames investigated by photoionization mass spectrometry and photoelectron spectroscopy07/25/2019

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Electrochemical synthesis of Anisole (cas 100-66-3) on platinum anode surface: Experiment and first-principle study07/24/2019

The anisole is synthesized by electrolyzing of phenol (or sodium phenate) and tetramethylammonium chloride (TMAC). The production forms on the Pt anode surface and not in the solution. There are adequate supplies of methyl radicals in all solutions. The phenoxyl radical is difficult to form in p...detailed

Deoxygenation in Anisole (cas 100-66-3) decomposition over bimetallic catalysts supported on HZSM-507/22/2019

This work investigated the deoxygenation reaction in anisole decomposition over HZSM-5 (HZ(25)) zeolite supported bimetallic catalysts to produce benzene, toluene and xylene (BTX). Experiments were performed in order to evaluate the synergistic effect between the two active metals with the focus...detailed

Experimental and kinetic modeling investigation on Anisole (cas 100-66-3) pyrolysis: Implications on phenoxy and cyclopentadienyl chemistry07/20/2019

In this work, the flow reactor pyrolysis of anisole was studied at pressures of 0.04 and 1 atm and temperatures from 850 to 1160 K. Comprehensive speciation was achieved using synchrotron vacuum ultraviolet photoionization mass spectrometry (SVUV-PIMS). A detailed kinetic model for anisole combu...detailed

Testing of Anisole (cas 100-66-3) and methyl acetate as additives to diesel and biodiesel fuels in a compression ignition engine07/21/2019

This paper investigates the effects of anisole and methyl acetate (as fuel additives) on the performance and emission characteristics of a compression-ignition (i.e., diesel) engine. Anisole and methyl acetate can be obtained from methylation of phenol and acetic acid, respectively. Phenol and a...detailed

100-66-3Relevant articles and documents

Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides

Ackermann, Lutz,Born, Robert,Spatz, Julia H.,Meyer, Daniel

, p. 7216 - 7219 (2005)

(Chemical Equation Presented) A couple of couplings: Air-stable diamino-and dioxophosphine oxides are used as preligands in the nickel-catalyzed Kumada cross-coupling reactions of aryl Grignard reagents. A sterically hindered preligand allows for highly efficient cross-coupling of aryl fluorides at ambient temperature (acac = acetylacetonate).

Ortho-selective methylation of phenol catalyzed by CeO2-MgO prepared by citrate process

Sato, Satoshi,Koizumi, Kaoru,Nozaki, Fumio

, p. 264 - 274 (1998)

Vapor-phase alkylation of phenol with methanol was investigated over CeO2-MgO catalysts prepared utilizing a molten mixture of the corresponding nitrates and citric acid. The CeO2-MgO had attractive catalytic performance without decay of activities at the temperature range between 450 and 550°C, and it had excellent selectivities to the sum of o-cresol and 2,6-xylenol higher than 98%. The CeO2-MgO catalysts were found to be mixtures of MgO and an interstitial solid solution of MgxCe1-x/2O2 as a result of XRD measurement. It is confirmed that citric acid used in the preparation heightens the dispersion of the solid solution in the MgO matrix. The pure CeO2, which also exhibited efficient ortho-selectivity, had only weak basic sites in the TPD experiment of adsorbed CO2, while the pure MgO with strong basicity showed very low reaction rate in the methylation. The solid solution of MgxCe1-x/2O2 in the CeO2-MgO catalyst probably provides active centers for the methylation of phenol. In the results of methanol decomposition, methanol was converted into CO, CO2, and CH4 over the CeO2-MgO catalysts, without producing dimethyl ether. The reaction mechanism of the ortho-methylation over the CeO2-MgO catalyst is speculated: the ortho position of phenol adsorbed perpendicularly on weak basic sites on the MgxCe1-x/2O2 solid solution is selectively alkylated by methanol which is possibly activated in the form of formyl or hydroxy methyl group rather than methyl cation.

-

Gilman et al.

, p. 2106 (1945)

-

Ionic liquids as recyclable and separable reaction media in Rh-catalyzed decarbonylation of aromatic and aliphatic aldehydes

Malcho, Phillip,Garca-Surez, Eduardo J.,Riisager, Anders

, p. 58151 - 58155 (2014)

Ionic liquids (ILs) have been applied as recyclable reaction media in the decarbonylation of aldehydes in the presence of a rhodium-phosphine complex catalyst. The performance of several new catalytic systems based on imidazolium-based ILs and [Rh(dppp)2]Cl (dppp: 1,3-diphenylphosphinopropane) were excellent in the decarbonylation of both aromatic and aliphatic aldehydes providing >99 yield of benzenes and alkanes, respectively. The catalytic performance depended, however, strongly on the employed IL and its thermal stability. In addition, the ILs afforded good catalyst immobilization as well as a biphasic system with the product allowing recovery and reuse of the employed catalyst.

Fluoroform-derived CuCF3 for low-cost, simple, efficient, and safe trifluoromethylation of aryl boronic acids in air

Novak, Petr,Lishchynskyi, Anton,Grushin, Vladimir V.

, p. 7767 - 7770 (2012)

Easy does it: Aryl boronic acids undergo smooth and selective trifluoromethylation with low-cost fluoroform-derived CuCF3 in DMF in non-dried air. The reaction occurs under mild conditions (1 atm, room temperature), exhibits unprecedented funct

PdCl2-catalyzed hydrogenolysis of a C-O bond in monoaryl sulfates by sodium phosphinate in an aqueous alkaline medium

Davydov, D. V.,Beletskaya, I. P.

, p. 573 - 575 (1993)

The hydrogenolysis of the C-O bond in monoaryl sulfates by the action of an excess of NaH2PO2 in the presence of catalytic amounts of PdCl2 and KOH is studied.The reaction proceeds chemoselectively with complete ester conversion to the corresponding arenes.

Protodecarboxylation of benzoic acids under radical conditions

Seo, Sangwon,Taylor, John B.,Greaney, Michael F.

, p. 8270 - 8272 (2012)

A new approach to protodecarboxylation is described that enhances the substrate scope for benzoic acids. The reaction uses oxidative radical conditions to decarboxylate a variety of acids in acetonitrile.

Regioselective hydrogenolysis of aryl ether C-O bonds by tungsten carbides with controlled phase compositions

Fang, Huihuang,Du, Junmou,Tian, Chenchen,Zheng, Jianwei,Duan, Xinping,Ye, Linmin,Yuan, Youzhu

, p. 10295 - 10298 (2017)

Evenly dispersed tungsten carbides with controlled phase compositions that exhibit an impressive capacity to carry out the regioselective hydrogenolysis of inert aryl ether C-O bonds instead of aliphatic C-O bonds to produce aromatic compounds are reported.

Nucleophilic Photoreaction of Chlorobenzene in Methanol as Studied by Emission Spectroscopy

Nagaoka, Shin-ichi,Takemura, Takeshi,Baba, Hiroaki

, p. 2082 - 2087 (1985)

The photoreaction of chlorobenzene in methanol has been studied by means of emission spectroscopy.Upon irradiation with UV light, chlorobenzene reacts with methanol to form anisole with a quantum yield of 0.049 at 18 deg C.Contrary to the case of chlorobenzene, the photoreaction of p-dichlorobenzene with methanol is not observed.By combining these results with those of our recent studies on the dual phosphorescence from low-lying triplet states of halogenated benzenes, it is suggested that the photoreaction of chlorobenzene with methanol, which is a nucleophilic substitution reaction, occurs in the 3(?,?*) state.From the temperature dependence of the quantum yield, the activation energy for the nucleophilic photoreaction is estimated to be larger by about 3 - 4 kcal mol-1 than the apparent activation energy for a combination of the nonradiative 3(?,?*)->S0 process and the homolytic dissociative process concerning the C-Cl bond in the 3(?,?*) state.It is suggested that the nucleophilic photoreaction contrasts with the radical reaction leading to the dissociation of the C-Cl bond; the latter reaction occurs in the 3(?,?*) state as well as in the 3(?,?*) state.

Efficient Catalysis of Hydrodediazoniations in Dimethylformamide

Wassmundt, Frederick W.,Kiesman, William F.

, p. 1713 - 1719 (1995)

For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions.A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields.Trapping experiments demonstrated the presence of free-radical intermediates.N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.

A Biomass-Derived Non-Noble Cobalt Catalyst for Selective Hydrodehalogenation of Alkyl and (Hetero)Aryl Halides

Sahoo, Basudev,Surkus, Annette-Enrica,Pohl, Marga-Martina,Radnik, J?rg,Schneider, Matthias,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias

, p. 11242 - 11247 (2017)

Hydrodehalogenation is a straightforward approach for detoxifications of harmful anthropogenic organohalide-based pollutants, as well as removal of halide protecting groups used in multistep syntheses. A novel sustainable catalytic material was prepared from biowaste (chitosan) in combination with an earth-abundant cobalt salt. The heterogeneous catalyst was fully characterized by transmission electron microscope, X-ray diffraction, and X-ray photoelectron spectroscopy measurements, and successfully applied to hydrodehalogenation of alkyl and (hetero)aryl halides with broad scope (>40 examples) and excellent chemoselectivity using molecular hydrogen as a reductant. The general usefulness of this method is demonstrated by successful detoxification of non-degradable pesticides and fire retardants. Moreover, the potential of the catalyst as a deprotection tool is demonstrated in a multistep synthesis of (±)-peronatin B (alkaloid).

Hydrodeoxygenation of guaiacol over carbon-supported metal catalysts

Chang, Jie,Danuthai, Tanate,Dewiyanti, Silvia,Wang, Chuan,Borgna, Armando

, p. 3041 - 3049 (2013)

Catalytic bio-oil upgrading to produce renewable fuels has attracted increasing attention in response to the decreasing oil reserves and the increased fuel demand worldwide. Herein, the catalytic hydrodeoxygenation (HDO) of guaiacol with carbon-supported non-sulfided metal catalysts was investigated. Catalytic tests were performed at 4.0MPa and temperatures ranging from 623 to 673K. Both Ru/C and Mo/C catalysts showed promising catalytic performance in HDO. The selectivity to benzene was 69.5 and 83.5% at 653K over Ru/C and 10Mo/C catalysts, respectively. Phenol, with a selectivity as high as 76.5%, was observed mainly on 1Mo/C. However, the reaction pathway over both catalysts is different. Over the Ru/C catalyst, the O-CH3 bond was cleaved to form the primary intermediate catechol, whereas only traces of catechol were detected over Mo/C catalysts. In addition, two types of active sites were detected over Mo samples after reduction in H2 at 973K. Catalytic studies showed that the demethoxylation of guaiacol is performed over residual MoOx sites with high selectivity to phenol whereas the consecutive HDO of phenol is performed over molybdenum carbide species, which is widely available only on the 10Mo/C sample. Different deactivation patterns were also observed over Ru/C and Mo/C catalysts.

The mechanism of phenol methylation on acid and basic zeolite catalysts

Borodina,Pomakhina,Ramishvili,Ponomareva,Rebrov,Ivanova

, p. 892 - 898 (2006)

The alkylation of phenol with methanol on HY and CsY/CsOH catalysts was studied in situ under static conditions by 13C NMR spectroscopy. Attention was largely given to the identification of intermediate compounds and mechanisms of anisole, cresol, and xylenol formation. The mechanisms of phenol methylation were found to be different on acid and basic catalysts. The primary process on acid catalysts was the dehydration of methanol to dimethyl ether and methoxy groups. This resulted in the formation of anisole and dimethyl ether, the ratio between which depended on the reagent ratio, which was evidence of similar mechanisms of their formation. Subsequent reactions with phenol gave cresols and anisoles. Cresols formed at higher temperatures both in the direct alkylation of phenol and in the rearrangement of anisole. The main alkylation product on basic catalysts was anisole formed in the interaction of phenolate anions with methanol; no cresol formation was observed. The deactivation of acid catalysts was caused by the formation of condensed aromatic hydrocarbons that blocked zeolite pores. The deactivation of basic catalysts resulted from the condensation of phenol and formaldehyde with the formation of phenol-formaldehyde resins. Nauka/Interperiodica 2006.

Reactivity in cleavage of dimethoxybenzenes by sodium in liquid ammonia

Bunnett, Joseph F.,Jenvey, Judy

, p. 8069 - 8073 (1996)

The sodium/liquid ammonia cleavage of the dimethoxybenzenes and related substances, reported in large part by Birch in 1947, has been re-examined with use of improved techniques. Remarkable patterns of reactivity (e.g., ortho > meta ? para) that he described are confirmed and extended. They are agreeably rationalized by means of a simple, approximate adaptation from MO theory.

Transfer hydrodehalogenation of aryl halides accelerated by a saturated sodium acetate aqueous solution

Xue, Zhimin,Zhao, Xinhui,Wang, Jinfang,Mu, Tiancheng

, p. 102193 - 102197 (2016)

Development of catalytic hydrodehalogenation of halogenated organic compounds is an important topic from the viewpoint of environment protection. Herein, we conducted the first work on the utilization of a saturated aqueous solution of sodium acetate (CH3COONa) as an efficient and environmentally-friendly reaction medium for transfer hydrodehalogenation of various aryl halides using Pd/C as the catalyst. It was found that the transfer hydrodehalogenation could be accelerated significantly by the saturated CH3COONa aqueous solution due to the surfactant-similar effect of CH3COONa and the activation of the C-Cl bond by the dissolved solvated ions.

Preparation of aromatic amines by copper-catalyzed coupling of boronic acids with aqueous ammonia

Jiang, Zhaoqiong,Wu, Zhiqing,Wang, Lixia,Wu, Di,Zhou, Xiangge

, p. 964 - 968 (2010)

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.

Efficient Decarbonylation of Furfural to Furan Catalyzed by Zirconia-Supported Palladium Clusters with Low Atomicity

Ishida, Tamao,Kume, Kurumi,Kinjo, Kota,Honma, Tetsuo,Nakada, Kengo,Ohashi, Hironori,Yokoyama, Takushi,Hamasaki, Akiyuki,Murayama, Haruno,Izawa, Yusuke,Utsunomiya, Masaru,Tokunaga, Makoto

, p. 3441 - 3447 (2016)

Decarbonylation of furfural to furan was efficiently catalyzed by ZrO2-supported Pd clusters in the liquid phase under a N2atmosphere without additives. Although Pd/C and Pd/Al2O3have frequently been used for decarbonylation, Pd/ZrO2exhibited superior catalytic performance compared with these conventional catalysts. Transmission electron microscopy and X-ray absorption fine structure measurements revealed that the size of the Pd particles decreased with an increase in the specific surface area of ZrO2. ZrO2with a high surface area immobilized Pd as clusters consisting of several (three to five) Pd atoms, whereas Pd aggregated to form nanoparticles on other supports such as carbon and Al2O3despite their high surface areas. The catalytic activity of Pd/ZrO2was enhanced with a decrease in particle size, and the smallest Pd/ZrO2was the most active catalyst for decarbonylation. When CeO2was used as the support, a decrease in Pd particle size with an increase in surface area was also observed. Single Pd atoms were deposited on CeO2with a high surface area, with a strong interaction through the formation of a Pd?O?Ce bond, which led to a lower catalytic activity than that of Pd/ZrO2. This result suggests that zero-valent small Pd clusters consisting of more than one Pd atom are the active species for the decarbonylation reaction. Recycling tests proved that Pd/ZrO2maintained its catalytic activity until its sixth use.

Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids

Lozada, Jerome,Liu, Zhibo,Perrin, David M.

, p. 5365 - 5368 (2014)

Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwe

Homolytic C-S bond scission in the desulfurization of aromatic and aliphatic thiols mediated by a Mo/Co/S cluster: Mechanistic aspects relevant HDS catalysis

Curtis, M. David,Druker, Scott H.

, p. 1027 - 1036 (1997)

The kinetics of the reaction of a series of aromatic and aliphatic thiols with cluster 1 were determined. These reactions form cluster 2 and the arene or alkane corresponding to the thiol: Cp'2Mo2Co2S3(CO)4 (1) + RSH → Cp'2Mo2Co2S4(CO)2 (2) + RH + 2CO. These reactions are first order in thiol and first order in cluster 1 with appreciable negative entropies of activation. These data suggest that the rate determining step of the desulfurization reaction is the initial association of the thiol to the cluster. The more nucleophilic thiolate anions react with 1 at -40°C to form an adduct in which the thiolate anion is bound η1 to the Co atom. At -25°C, the initial adduct rearranges to a fluxional μ2, η1-bound thiolate. The fluxional process is proposed to involve a concerted 'walking' of the thiolate and a μ2-bound sulfide ligand on the surface of the cluster. Near 35°C, the thiolate-cluster adduct undergoes C-S bond homolysis to give the paramagnetic anion of cluster 1 and the phenyl or alkyl radical. The radical nature of the C-S bond cleavage was confirmed by the desulfurization of the radical clock reagents, cyclopropylmethanethiol and -thiolate anion, that form the cyclopropylmethyl radical which rearranged to the butenyl radical. The possible similarity in the C-S bond cleavage mechanism in these desulfurization reactions to those occurring in hydrodesulfurization (HDS) over Co/Mo/S catalysts is discussed.

The Mechanism of Titanium Complex-Catalyzed Reduction of Aryl Halides by Sodium Borohydride Is Strongly Solvent Dependent

Liu, Yumin,Schwartz, Jeffrey

, p. 940 - 942 (1994)

The titanium complex-catalyzed reduction of aryl halides by sodium borohydride in dimethylacetamide (DMA) or ethers proceeds by electron transfer from a reduced titanium species, yielding an intermediate aryl radical.

Birch, A. J.,Cross, P.E.,Fitton, H.

, (1965)

Liquid chromatography-photolysis-electrochemical detection for organoiodides. 2. Operative mechanisms.

Selavka,Krull

, p. 2704 - 2709 (1987)

-

Stannylated Vinylic addition polynorbornene: Probing a reagent for friendly tin-mediated radical processes

García-Loma, Rodrigo,Alb é Niz, Ana C.

, p. 4247 - 4254 (2017)

Vinylic addition polynorbornenes (VA-PNB) with stannyl functional groups have been prepared and used in tinmediated radical dehalogenation reactions. The aliphatic and robust scaffold of VA-PNB is well suited for a support in radical processes. VA-PNB-(CH2)nSnHBu2 can be used as a stoichiometric reagent and VA-PNB-(CH2)nSnBu2Cl as a catalyst in the presence of a hydride donor for the reduction of RBr. The mixture KF (aq.)/polymethylhydrosiloxane (PMHS) is the most convenient hydride source to generate VA-PNB-(CH2)nSnHBu2 in situ. Al-though quite popular in this context, boron hydrides, being a source of radicals themselves, are not adequate to correctly evaluate the performance of the anchored organotin group. VAPNB-(CH2)4SnBu2Cl can be recycled and, even if it loses activity upon reuse, it is still useful after ten cycles. The stannylated VAPNB can be separated from the products by simple filtration, and it leads to very low tin contamination (at least 250 times lower than that with use of conventional separation methods).

Role of copper- or cerium-promoters on NiMo/Γ-Al2O3 catalysts in hydrodeoxygenation of guaiacol and bio-oil

Sangnikul, Patiphat,Phanpa, Chanisara,Xiao, Rui,Zhang, Huiyan,Reubroycharoen, Prasert,Kuchonthara, Prapan,Vitidsant, Tharapong,Pattiya, Adisak,Hinchiranan, Napida

, p. 151 - 160 (2019)

Effect of copper (Cu) or cerium (Ce) as promoters for nickel-molybdenum/γ-alumina (NiMo/γ-Al2O3) catalyst on the hydrodeoxygenation (HDO) of guaiacol (GUA), a model oxygenated compound found in a bio-oil derived from woody biomass, was comparatively investigated. The addition of Cu- or Ce-promoters affected the physicochemical properties of the NiMo catalyst. The NiMo catalyst promoted by Cu showed the higher reducibility, whilst the Ce-promoter (2–8 wt% based on γ-Al2O3 content) provided the NiMo catalyst with a higher distribution of active metals and induced a greater difficulty in the reduction under hydrogen (H2) atmosphere. For the HDO of GUA at a mild reaction condition (10 bar initial H2 pressure and 300 °C) in the absence of solvent, the Cu-promoter enhanced the hydrogenation activity of the NiMo catalyst to convert GUA to phenol and methylphenols, one-atomic oxygen species. Whereas, the addition of Ce obviously inhibited the formation of coke on the catalyst surface after a long reaction period (6 h) and gave a higher GUA conversion level with increasing yield of phenols. For the HDO of real bio-oil obtained from the fast pyrolysis of cassava rhizome, the NiMo catalysts promoted by Cu or Ce at 4 wt% based on the γ-Al2O3 content showed a higher performance at eliminating the oxygenated compounds in the bio-oil, reducing the oxygen/carbon (O/C) molar ratio by over seven-fold from 1.75 to 0.24–0.25. Moreover, the gross heating value of the bio-oil was improved from 21.5 to ca. 29.0 MJ/kg after the HDO process. However, the addition of the Cu or Ce promoter did not inhibit coke deposition, possibly due to the acidic properties of the bio-oil that deteriorated the catalyst performance by metal leaching.

Continuous in situ generation, separation, and reaction of diazomethane in a dual-channel microreactor

Maurya, Ram Awatar,Park, Chan Pil,Lee, Jang Han,Kim, Dong-Pyo

, p. 5952 - 5955 (2011)

A fierce dog: A method for the continuous in-situ on-demand generation, separation, and reaction of diazomethane in a dual-channel microreactor has been developed (see picture; Diazald=N-methyl-N-nitroso-p-toluenesulfonamide). The microchemical system allows a variety of diazomethane reactions to be performed without the most common problems of preparation, handling, transfer, and decomposition.

Highly Selective Hydrodeoxygenation of Lignin to Naphthenes over Three-Dimensional Flower-like Ni2P Derived from Hydrotalcite

Chen, Guanyi,Diao, Xinyong,Ji, Na,Jia, Zhichao,Li, Changzhi,Li, Xinxin,Liu, Caixia,Liu, Qingling,Lu, Xuebin,Ma, Longlong,Song, Chunfeng,Wang, Shurong,Zhao, Yujun

, p. 1338 - 1356 (2022/02/07)

A strategy for low-temperature synthesis of hydrotalcite-based nickel phosphide catalysts (Ni2P-Al2O3) with flower-like porous structures was proposed. The in situ reduction of red phosphorus at 500 °C enables Ni2P catalysts with small particle size and abundant active and acidic sites, which facilitate the activation of substrates and H2. In the hydrodeoxygenation of guaiacol, a 100% conversion and 94.5% yield of cyclohexane were obtained over the Ni2P-Al2O3 catalyst under 5 MPa H2 at 250 °C for 3 h. Other lignin-derived phenolic compounds could also afford the corresponding alkanes with yields higher than 85%. Moreover, Ni2P-Al2O3 exhibited high hydrodeoxygenation activity in the deconstruction of more complex wood structures, including lignin oil and real lignin. Among the two different types of Ni sites of Ni(1) and Ni(2) in Ni2P, density functional theory (DFT) calculations showed that the Ni(2) site, highly exposed on the Ni2P-Al2O3 surface, possesses a stronger ability to break C-OH bonds during the hydrodeoxygenation of guaiacol in comparison with the Ni(1) site.

Protodesilylation of Arylsilanes by Visible-Light Photocatalysis

García Manche?o, Olga,Kuhlmann, Jan H.,Uygur, Mustafa

supporting information, p. 1689 - 1694 (2022/03/14)

The first visible-light-mediated photocatalytic, metal- and base-free protodesilylation of arylsilanes is presented. The C(sp2)-Si bond cleavage process is catalyzed by a 5 mol % loading of a commercially available acridinium salt upon blue-light irradiation. Two simple approaches have been identified employing either aerobic or hydrogen atom transfer cocatalytic conditions, which enable the efficient and selective desilylation of a broad variety of simple and complex arylsilanes under mild conditions.

Heterogeneously Catalyzed Selective Decarbonylation of Aldehydes by CeO2-Supported Highly Dispersed Non-Electron-Rich Ni(0) Nanospecies

Matsuyama, Takehiro,Yatabe, Takafumi,Yabe, Tomohiro,Yamaguchi, Kazuya

, p. 13745 - 13751 (2021/11/17)

Aldehyde decarbonylation has been extensively investigated, primarily using noble-metal catalysts; however, nonprecious-base-metal-catalyzed aldehyde decarbonylation has been hardly reported. We have established an efficient selective aldehyde decarbonylation reaction with a broad substrate scope and functional group tolerance utilizing a heterogeneous Ni(0) nanospecies catalyst supported on CeO2. The high catalytic performance is attributable to the highly dispersed and non-electron-rich Ni(0) nanospecies, which possibly suppress a side reaction producing esters and adsorbed CO-derived inhibition of the catalytic turnover, according to detailed catalyst characterization and kinetic evaluation.

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