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108-90-7

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108-90-7 Usage

Chemical Description

Different sources of media describe the Chemical Description of 108-90-7 differently. You can refer to the following data:
1. Chlorobenzene is a colorless, flammable liquid that is used as a solvent and in the production of other chemicals.
2. Chlorobenzene is an aromatic organic compound with the formula C6H5Cl.
3. Chlorobenzene is another solvent used in the reaction.
4. Chlorobenzene is a colorless liquid used as a solvent and in the production of other chemicals.
5. Chlorobenzene is a solvent and benzoyl peroxide is a radical initiator used in the bromination reaction.

Description

Chlorobenzene is a monocyclic aromatic compound with one hydrogen atom on the benzene ring substituted with one chlorine. It is produced by chlorination of benzene in the liquid phase with a catalyst. Chlorobenzene is a colourless, flammable liquid with a sweet almond-like odor, at ambient temperature with a relatively high vapour pressure, moderate octanol-water partition coefficient (log 2.8) and moderate to low water solubility (497.9 mg/L @ 25℃). Chlorobenzene has a high solubility in nonpolar solvents, however, it is almost insoluble in water. Technical grade Chlorobenzene is typically 99% pure with < 0.05% benzene and < 0.1% dichlorobenzenes as contaminants. It is a common solvent and a widely used intermediate in the manufacture of other chemicals. Rhodococcus phenolicus is a bacterium species able to degrade chlorobenzene as sole carbon sources.

Uses

Different sources of media describe the Uses of 108-90-7 differently. You can refer to the following data:
1. Chlorobenzene is used primarily as raw material for the synthesis of o- and p-nitrochlorobenzene and 2,4-dinitrochlorobenzene.Important quantitative chemical conversions other than the production of nitrochlorobenzenes are the production of diphenyl oxide and diphenyldichlorosilane. Chlorobenzene is mainly used as raw material for the synthesis of chemicals including triphenylphosphine (catalyst for organic synthesis), phenylsilane, and thiophenol (pesticide and pharmaceutical intermediate). It is also used as raw material for the synthesis of solvent for organic synthesis reactions including methylenediphenyldiisocyanate, urethane raw material, agricultural adjuvants, paint and ink, and cleaning solvent for electronics. manufacture of phenol, aniline, DDT; solvent for paints; heat transfer medium. Chlorobenzene is used as a process solvent in the production of isocyanates such as MDI and TDI and as a solvent in various crop protection formulations. It is further used as a solvent in condensation reactions in the dyes industry. Chlorobenzene is a basic substance used in chemical syntheses with 95% of the quantity used converted in closed systems to intermediate and final products. It is used as a process solvent in the manufacture of three indigoid dyes and pigments. All the pigments and dyes are thioindigoid colors. Chlorobenzene is an example of haloarenes which is formed by mono substitution of benzene ring. When chlorobenzene is fused with sodium hydroxide at 623K and 320 atm sodium phenoxide is produced. Finally, sodium phenoxide on acidification gives phenols.
2. Chlorobenzene is a halogenated benzene that is used as a solvent for paints, as a heat transfer medium, and in the manufacture of phenol, aniline and nitrochlorobenzenes. Now chlorobenzene is mainly used as a solvent for pesticide formulations, diisocyanate manufacture, degreasing automobile parts, and for the production of nitrochlorobenzene and chemical toxicity QSAR research for agricultural pollution.

Toxicity

The toxic effects of chlorobenzene on humans were exhaustion, nausea, lethargy, headache and irritation to the upper respiratory tract and eye. Contact of chlorobenzene with the skin induced irritation. No reports were obtained on sensitization by chlorobenzene in this investigation. The oral LD50 values of chlorobenzene were 1,445 mg/kg in mice, 1,427 to 3,400 mg/kg in rats and 2,250 to 2,830 mg/kg in rabbits. The LC50s following 6-hr inhalation exposure were 1,889 ppm in mice and 2,968 ppm in rats.

Chemical Properties

Chlorobenzene, also known as monochlorobenzene or MCB, is a colourless flammable liquid with an aromatic almond-like odor, Chlorination of benzene in the presence of a catalyst (FeCl3 or AICI3) yields chlorobenzene as the first product. It is insoluble in water and miscible with organic solvents. Chlorobenzene has a good solvency for fats, oils, resins, polymers, binders, rubber, and chlorinated rubber. Cellulose ethers dissolve in the presence of small amounts of alcohols; cellulose nitrate is insoluble. Chlorobenzene is a solvent in the production of bitumen and asphalt coatings for building protection.

Physical properties

Clear, colorless, flammable liquid with a sweet almond, medicinal or mothball-like odor. An odor threshold concentration of 210 ppbv was reported by Leonardos et al. (1969). At 40 °C, the lowest concentration at which an odor was detected was 190 μg/L. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L (Young et al., 1996). The average least detectable odor threshold concentration in water at 60 °C was 0.08 mg/L (Alexander et al., 1982). Cometto-Muiz and Cain (1994) reported an average nasal pungency threshold concentration of 10,553 ppmv. Chlorobenzene can evaporate when exposed to air. It dissolves slightly when mixed with water. It is moderately soluble in water; up to 1,000 milligrams will mix with a liter of water. Chlorobenzene is slightly persistent in water, with a half-life of between 2 to 20 days. It persists in soil (several months), in air (3.5 days), and water (less than 1 day).

Definition

ChEBI: Chlorobenzene is the simplest member of the class of monochlorobenzenes, that is benzene in which a single hydrogen has been substituted by a chlorine. It has a role as a solvent.

Preparation

Chlorobenzene is produced by chlorination of benzene in the presence of a catalyst, and is produced as an end product in the reductive chlorination of di- and trichlorobenzenes.

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 6297, 1952 DOI: 10.1021/ja01144a523Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1

General Description

Chlorobenzene is a colorless to clear, yellowish liquid with a sweet almond-like odor. Flash point 84°F. Practically insoluble in water and somewhat denser than water (9.2 lb / gal). Vapors heavier than air. It can be converted to phenol by reaction with sodium hydroxide under extreme conditions (300°C and 200 atmospheres pressure). Used to make pesticides, dyes, and other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Chlorobenzene undergoes a sometimes explosive reaction with powdered sodium or phosphorus trichloride + sodium. May react violently with dimethyl sulfoxide. Reacts vigorously with oxidizing agents. Attacks some forms of plastic, rubber and coatings. Forms a shock sensitive solvated salt with silver perchlorate.

Hazard

A possible carcinogen. Avoid inhalation and skin contact. Moderate fire risk. Explosive limits 1.8–9.6%.

Health Hazard

Irritating to skin, eyes and mucous membranes. Repeated exposure of skin may cause dermatitis due to defatting action. Chronic inhalation of vapors or mist may result in damage to lungs, liver, and kidneys. Acute vapor exposures can cause symptoms ranging from coughing to transient anesthesia and central nervous system depression. Limited information is available on the acute (short-term) effects of chlorobenzene. Acute inhalation exposure of animals to chlorobenzene produced narcosis, restlessness, tremors, and muscle spasms. Chronic (long-term) exposure of humans to chlorobenzene affects the central nervous system (CNS). Signs of neurotoxicity in humans include numbness, cyanosis, hyperesthesia (increased sensation), and muscle spasms. No information is available on the carcinogenic effects of chlorobenzene in humans. EPA has classified chlorobenzene as a Group D, not classifiable as to human carcinogenicity.

Fire Hazard

Flammable liquid; flash point (closed cup) 29°C (84°F); vapor pressure 8.8 torr at 20°C (68°F); autoignition temperature 638°C (1180°F). When heated to decomposition this compound emits toxic fumes of hydrogen chloride gas, CO and CO2.Chlorobenzene vapors form explosive mixtures with air within the range 1.3-7.1% by volume in air. It is incompatible with strong oxidizing agents and dimethyl sulfoxide. Dimethyl sulfoxide decom poses violently in contact with chloroben zene (NFPA 1997). Many metal perchlorates, such as those of silver and mercury, may form shock-sensitive solvated perchlorates that may explode on impact.

Flammability and Explosibility

Flammable

Safety Profile

Suspected carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. Strong narcotic with slight irritant qualities. Dichlorobenzols are strongly narcotic. Little is known of the effects of repeated exposures at lower concentrations, but it may cause hdney and liver damage. The industrial illnesses reported may possibly be due to nitrobenzol. Dangerous fire hazard when exposed to heat or flame. Moderate explosion hazard when exposed to heat or flame. Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodtum. Violent reaction with AgClO4. Reacts vigorously with oxidizers. See also CHLORINATED HYDROCARBONS, AROMATIC. To fight fire, use foam, CO2, dry chemical, water to blanket fire. Associated with EPA Superfund sites

Potential Exposure

Chlorobenzene is used in the manufacture of aniline, phenol, and chloronitrobenzene; as an intermediate in the manufacture of dyestuffs and many pesticides, as a solvent; and emulsifier.

Carcinogenicity

Chlorobenzene was not mutagenic in a variety of bacterial and yeast assays. Existing data suggest that genotoxicity may not be an area of concern for chlorobenzene exposure in humans.

Environmental Fate

Chlorobenzene's production and use as a chemical intermediate, solvent, and heat transfer medium may result in its release to the environment through various waste streams. If released to air, chlorobenzene will exist solely as a vapor in the atmosphere. Photochemically produced hydroxyl radicals will ultimately degrade vapor-phase chlorobenzene in less than 24h.Biological. In activated sludge, 31.5% of the applied chlorobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985). A mixed culture of soil bacteria or a Pseudomonas sp. transformed chlorobenzene to chlorophenol (Ballschiter and Scholz, 1980). Pure microbial cultures isolated from soil hydroxylated chlorobenzene to 2- and 4-chlorophenol (Smith and Rosazza, 1974). Chlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum. At a concentration of 5 mg/L, biodegradation yields at the end of 1 and 2 wk were 89 and 100%, respectively. At a concentration of 10 mg/L, significant degradation with gradual adaptation was observed.Complete degradation was not observed until after the 3rd week of incubation (Tabak et al.,1981).https://www.epa.gov

Shipping

UN1134 Chlorobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

The main impurities are likely to be chlorinated impurities originally present in the *benzene used in the synthesis of chlorobenzene, and also unchlorinated hydrocarbons. A common purification procedure is to wash it several times with conc H2SO4 then with aqueous NaHCO3 or Na2CO3, and water, followed by drying with CaCl2, K2CO3 or CaSO4, then with P2O5, and distilling. It can also be dried with Linde 4A molecular sieve. Passage through, and storage over, activated alumina has been used to obtain low conductance material. [Flaherty & Stern J Am Chem Soc 80 1034 1958, Beilstein 5 H 199, 5 IV 640.]

Toxicity evaluation

In the ambient atmosphere, chlorobenzene will exist as a vapor, and will be degraded by reaction with photochemically produced hydroxyl radicals, with an estimated half-life of 21 days. It can be removed from the air by rain. Photolysis halflives of 4–18 h were measured in aqueous media. If released to soil, chlorobenzene is expected to have very high to moderate mobility based on a Koc range of 4.8–313. Moist soil surfaces will favor volatilization based upon Henry’s Law constant of 3.11×103 atm-cu m mol-1. Chlorobenzene may volatilize from dry soil surfaces as well. If released into water, chlorobenzene may adsorb to suspended solids and sediment based on the Koc values. Volatilization from water surfaces is expected to be an important fate process based on this compound’s Henry’s Law constant. Estimated volatilization half-lives for a model river and model lake are 3.4 h and 4.3 days, respectively. Reported bioconcentration in aquatic organisms is low to high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Biodegradation results are variable based on soil type and microbial diversity. In river water, the biodegradation half-life was reported to be 150 and 75 days in the sediment.

Incompatibilities

Reacts violently with strong oxidizers; dimethyl sulfoxide; sodium powder; silver perchlorate; causing fire and explosion hazard. Attacks some plastics, rubber, and coatings. Decomposes on heating, producing phosgene and hydrogen chloride fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 108-90-7 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, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 108-90:
(5*1)+(4*0)+(3*8)+(2*9)+(1*0)=47
47 % 10 = 7
So 108-90-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H6.ClH/c1-2-4-6-5-3-1;/h1-6H;1H/p-1

108-90-7 Well-known Company Product Price

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  • Alfa Aesar

  • (36401)  Chlorobenzene, ACS, 99.5%   

  • 108-90-7

  • 500ml

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (36401)  Chlorobenzene, ACS, 99.5%   

  • 108-90-7

  • 1L

  • 734.0CNY

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  • Alfa Aesar

  • (36401)  Chlorobenzene, ACS, 99.5%   

  • 108-90-7

  • 4L

  • 1638.0CNY

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  • Alfa Aesar

  • (36401)  Chlorobenzene, ACS, 99.5%   

  • 108-90-7

  • *4x1L

  • 1802.0CNY

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  • Alfa Aesar

  • (H27688)  Chlorobenzene, HPLC Grade, 99+%   

  • 108-90-7

  • 1000ml

  • 841.0CNY

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  • Alfa Aesar

  • (H27688)  Chlorobenzene, HPLC Grade, 99+%   

  • 108-90-7

  • 2500ml

  • 1686.0CNY

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  • Alfa Aesar

  • (22922)  Chlorobenzene, HPLC Grade, 99.5%   

  • 108-90-7

  • 1L

  • 574.0CNY

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  • Alfa Aesar

  • (22922)  Chlorobenzene, HPLC Grade, 99.5%   

  • 108-90-7

  • 4L

  • 1852.0CNY

  • Detail
  • Alfa Aesar

  • (22922)  Chlorobenzene, HPLC Grade, 99.5%   

  • 108-90-7

  • *4x1L

  • 1972.0CNY

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  • Alfa Aesar

  • (22921)  Chlorobenzene, Spectrophotometric Grade, 99.9%   

  • 108-90-7

  • 500ml

  • 293.0CNY

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  • Alfa Aesar

  • (22921)  Chlorobenzene, Spectrophotometric Grade, 99.9%   

  • 108-90-7

  • 1L

  • 418.0CNY

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  • Alfa Aesar

  • (22921)  Chlorobenzene, Spectrophotometric Grade, 99.9%   

  • 108-90-7

  • 4L

  • 1461.0CNY

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108-90-7SDS

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 chlorobenzene

1.2 Other means of identification

Product number -
Other names monochloro-benzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Volatile organic compounds
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:108-90-7 SDS

108-90-7Synthetic route

3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With potassium carbonate; iron pentacarbonyl In methanol at 60℃; under 760 Torr; for 8h;100%
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 10 min; Yield given. Multistep reaction;
With 2,2'-azobis(isobutyronitrile); sodium methylate In methanol at 70.2℃; Mechanism; var. iodobenzenes;
With tetrahydrofuran; 1,10-Phenanthroline; potassium tert-butylate at 70℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;90 %Chromat.
With potassium tert-butylate at 80℃; for 12h; Inert atmosphere; Schlenk technique;88 %Chromat.
2-iodochlorobenzene
615-41-8

2-iodochlorobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With potassium carbonate; iron pentacarbonyl In methanol at 60℃; under 760 Torr; for 2h;100%
With hydrogen cation; copper 1) THF, 25 deg C, 10 min; Yield given. Multistep reaction;
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 10 min; Yield given. Multistep reaction;
With sodium methylate In methanol; dimethyl sulfoxide at 50.1℃; Rate constant; Mechanism; other iodoarenes;
pentan-1-ol
71-41-0

pentan-1-ol

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

A

1-bromo-4-pentyloxybenzene
30752-18-2

1-bromo-4-pentyloxybenzene

B

2-chlorophenyl pentyl ether
51241-39-5

2-chlorophenyl pentyl ether

C

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With potassium hydroxide; PEG-6000 at 150℃; for 6h; Yields of byproduct given;A n/a
B 100%
C n/a
benzene
71-43-2

benzene

A

nitrobenzene
98-95-3

nitrobenzene

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With potassium chloride; potassium nitrate; trifluoroacetic acid at 20℃; for 5.04h; Product distribution; Mechanism; other time, other ratio of reagents, other solvent;A 100%
B n/a
tetraphenylbismuth chloride
42967-53-3

tetraphenylbismuth chloride

A

triphenylbismuthane
603-33-8

triphenylbismuthane

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
In not given decomposition at room temp.;A 100%
B 100%
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

A

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 20h; Inert atmosphere;A 0.2%
B 99.8%
With nickel at 80℃; for 4h; Product distribution; Ni derived from NiBr2 or from NiCl2; var. times;
With nickel at 80℃; for 4h;A 77 % Chromat.
B 25 % Chromat.
bromochlorobenzene
106-39-8

bromochlorobenzene

A

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 57h; Inert atmosphere;A 0.8%
B 99.2%
In 1,2-dimethoxyethane at 85℃; Product distribution; var. solvents; var. times; Ni from NiI2 or NiBr2;
With nickel In 1,2-dimethoxyethane at 85℃; for 20h;A 61 % Chromat.
B 32 % Chromat.
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; air In N,N-dimethyl-formamide at 70℃; for 24h;99%
With butyl magnesium bromide; zirconocene dichloride In tetrahydrofuran for 1h; Ambient temperature;98%
With lithium aluminium tetrahydride; di-tert-butyl peroxide In tetrahydrofuran for 0.7h; Irradiation;96%
2-iodochlorobenzene
615-41-8

2-iodochlorobenzene

A

chlorobenzene
108-90-7

chlorobenzene

B

2,2'-Dichlorobiphenyl
13029-08-8

2,2'-Dichlorobiphenyl

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 36h; Inert atmosphere;A 98.4%
B 1.6%
bromochlorobenzene
106-39-8

bromochlorobenzene

A

chlorobenzene
108-90-7

chlorobenzene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction;A 98%
B n/a
With lithium aluminium tetrahydride; Tridecane In diethyl ether at 0℃; for 0.25h; Irradiation; Title compound not separated from byproducts;A 77 % Chromat.
B 18 % Chromat.
With Amberlite IRA-400; borohydride form; nickel diacetate In methanol at 20℃; for 3h; Reduction;A 56 % Chromat.
B 19 % Chromat.
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

A

chlorobenzene
108-90-7

chlorobenzene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction;A 98%
B n/a
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With dibutylbis(cyclopentadienyl)zirconium for 1h; Ambient temperature;98%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 70℃; Rate constant;
With tetrahydrofuran; 1,10-Phenanthroline; potassium tert-butylate at 110℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;85 %Chromat.
With ZnSe/CdS core/shell QDs; N-ethyl-N,N-diisopropylamine In hexane at 25℃; for 48h; Irradiation; Inert atmosphere;51 %Chromat.
bromochlorobenzene
106-39-8

bromochlorobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With butyl magnesium bromide; zirconocene dichloride In tetrahydrofuran for 6h; Ambient temperature;97%
With lithium aluminium tetrahydride; di-tert-butyl peroxide In tetrahydrofuran for 1h; Irradiation;92%
With tetrabutoxytitanium; diisobutylaluminium hydride In diethyl ether for 6h; Heating;91%
(C6H5)4Sb(1+)*H3COC6H4S(1-)*0.11CHCl3 = (C6H5)4SbSC6H4OCH3*0.11CHCl3

(C6H5)4Sb(1+)*H3COC6H4S(1-)*0.11CHCl3 = (C6H5)4SbSC6H4OCH3*0.11CHCl3

A

4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

B

H3COC6H4SCCl3

H3COC6H4SCCl3

C

4,4'-dimethoxyphenyl disulfide
5335-87-5

4,4'-dimethoxyphenyl disulfide

D

triphenylantimony
603-36-1

triphenylantimony

E

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
In tetrachloromethane byproducts: biphenyl; reflux; not isolated, GLC;A 36%
B 40%
C 22%
D 96%
E 33%
dichloro(o-chlorophenyl)phenylsilane
36964-86-0

dichloro(o-chlorophenyl)phenylsilane

A

9,9-dichloro-9-silafluorene
18030-58-5

9,9-dichloro-9-silafluorene

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

chlorobenzene
108-90-7

chlorobenzene

D

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With hexachlorodisilane at 500℃; gas phase; Further byproducts given;A 95%
B 0.3 g
C 0.8 g
D 0.2 g
(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)phenylgold

(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)phenylgold

(Dichloroiodo)benzene
932-72-9

(Dichloroiodo)benzene

A

chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I)

chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I)

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene Solvent; Temperature; UV-irradiation;A 95%
B 95%
bromobenzene
108-86-1

bromobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With iron(III) chloride; sodium chloride In acetonitrile for 10h; Kinetics; Catalytic behavior; Quantum yield; Reagent/catalyst; Irradiation; Green chemistry;94.3%
With sodium chlorite; trichloroacetic acid In dichloromethane for 3h; Substitution;92%
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 12h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;90%
methanol
67-56-1

methanol

benzene diazonium chloride
100-34-5

benzene diazonium chloride

A

biphenyl
92-52-4

biphenyl

B

methoxybenzene
100-66-3

methoxybenzene

C

chlorobenzene
108-90-7

chlorobenzene

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
With trans-bis[1,2-bis(diphenylphosphino)ethane]bis(dinitrogen)tungsten(0) In methanol for 0.25h; Product distribution; Ambient temperature; reagents' ratio and mode of the mixing dependence; also with EtOH, CH3OD, CD3OD;A 1.7%
B 1.6%
C 0.4%
D 93.1%
nitrobenzene
98-95-3

nitrobenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With Dichlorophenylphosphine In various solvent(s) at 170℃; for 5h;93%
With thionyl chloride at 160 - 200℃; im Rohr;
With chlorine at 22.85℃; under 700 Torr; Kinetics; Further Variations:; Pressures; Substitution;
With tetrachloromethane at 250℃; for 7h; Inert atmosphere; Autoclave;90 %Spectr.
With thionyl chloride at 160 - 200℃; im Rohr;
carbon monoxide
201230-82-2

carbon monoxide

p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

A

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With palladium diacetate; polymethylhydrosiloxane In diethyl ether; acetonitrile under 7355.08 Torr; for 12h;A 93%
B n/a
benzoic acid
65-85-0

benzoic acid

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With trichloroisocyanuric acid; bromine In tetrachloromethane at -10 - 100℃; for 6h; Solvent; Temperature; Concentration; Time; Photolysis;93%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

A

PCB 11
2050-67-1

PCB 11

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 29h; Inert atmosphere;A 7.2%
B 92.8%
benzoyl chloride
98-88-4

benzoyl chloride

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
palladium on activated charcoal In gas at 360℃;92%
With nickel at 420℃;
benzenediazonium; tetrachloro cuprate(II)

benzenediazonium; tetrachloro cuprate(II)

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;92%
2-(2-chlorophenyl)-1-ethanol
19819-95-5

2-(2-chlorophenyl)-1-ethanol

chlorobenzene
108-90-7

chlorobenzene

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;92%
4-chlorophenyltrimethylsilane
10557-71-8

4-chlorophenyltrimethylsilane

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;91%
In sulfuric acid; acetic acid at 50℃;
In sulfuric acid; acetic acid at 50℃; Rate constant; 1.) other solvetnts, 2.) k (excit.);
With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 6h; Sealed tube; Schlenk technique;89 %Chromat.
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

A

chlorobenzene
108-90-7

chlorobenzene

B

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; manganese(II) acetate; trifluoroacetic acid In acetonitrile at 80℃; under 15001.5 Torr; for 21h; Mechanism; chemoselective reaction;A n/a
B 91%
benzoin phenylhydrazone ethyl ether
64357-12-6

benzoin phenylhydrazone ethyl ether

A

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

B

2-ethoxy-1,2-diphenyl-ethanone
574-09-4

2-ethoxy-1,2-diphenyl-ethanone

C

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

D

benzaldehyde
100-52-7

benzaldehyde

E

chlorobenzene
108-90-7

chlorobenzene

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
With copper dichloride for 5h; Product distribution; Heating; variation of time;A 90%
B 10%
C 40%
D 10%
E n/a
F n/a
5-(2-Chloro-phenoxy)-1-phenyl-1H-tetrazole
86379-23-9

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

A

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

1-phenyl-5-hydroxytetrazole

B

chlorobenzene
108-90-7

chlorobenzene

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sodium hypophosphite; palladium on activated charcoal In ethanol; water; benzene for 4.16667h; Heating;A n/a
B 10%
C 90%
palladium on activated charcoal In ethanol; benzene Mechanism; Product distribution; various reagents, temperatures and reaction times;
phenylzinc chloride
28557-00-8

phenylzinc chloride

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With N-chloro-succinimide; palladium (II) ion In tetrahydrofuran at 45℃; for 16h;90%
chlorobenzene
108-90-7

chlorobenzene

4,4'-dichlorodiphenyl sulphone
80-07-9

4,4'-dichlorodiphenyl sulphone

Conditions
ConditionsYield
With sulfuric acid; trifluoroacetic acid; trifluoroacetic anhydride; Η-β Zeochem at 10 - 53℃; for 4h; Product distribution / selectivity;100%
With sulfuric acid at 20℃; for 4h;95.02%
Stage #1: chlorobenzene With aluminum (III) chloride; thionyl chloride In water at 50 - 90℃; for 3h;
Stage #2: With sulfuric acid; dihydrogen peroxide; acetic acid In water at 80℃; for 3h;
93.8%
chlorobenzene
108-90-7

chlorobenzene

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h; Product distribution; effect of bases and solvents on the hydrodechlorination;100%
With potassium hydroxide; hydrogen; palladium on activated charcoal; Aliquat 336 In 2,2,4-trimethylpentane at 50℃; for 4.5h;100%
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h;100%
styrene
292638-84-7

styrene

chlorobenzene
108-90-7

chlorobenzene

(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

Conditions
ConditionsYield
With C50H64Cl2N12Pd2(6+)*6F6P(1-); sodium acetate In N,N-dimethyl-formamide at 140℃; for 24h; Reagent/catalyst; Heck Reaction;100%
With cesium acetate; PdCl[(C6H3)(OP(i-Pr)2)2-2,6] In 1,4-dioxane at 120℃; for 120h; Arylation; Heck reaction;99%
With tetrabutylammonium acetate; palladium diacetate; DavePhos In 1,4-dioxane at 80℃; for 24h; Heck reaction; Inert atmosphere; Sealed tube;99%
pentan-1-ol
71-41-0

pentan-1-ol

chlorobenzene
108-90-7

chlorobenzene

(pentyloxy)benzene
2050-04-6

(pentyloxy)benzene

Conditions
ConditionsYield
With potassium hydroxide; PEG-6000 at 150℃; for 6h;100%
chlorobenzene
108-90-7

chlorobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
nickel(II) In tetrahydrofuran for 18h; Product distribution; other catalyst, other solvents; other Grignard compounds and alkyl or vinyl halides;100%
With CpNi[1-(ethoxycarbonyl)methyl-3-(3,5-dimethylbenzyl)benzimidazolin-2-ylidene]Br In tetrahydrofuran at 25℃; for 3h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;97%
With Pd/Al(OH)3 In toluene at 140℃; for 36h; Kumada Cross-Coupling; Inert atmosphere;94%
chlorobenzene
108-90-7

chlorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction;100%
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol for 0.166667h; Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere;100%
With potassium carbonate In methanol at 100℃; for 0.0833333h; Suzuki-Miyaura Coupling; Microwave irradiation;100%
chlorobenzene
108-90-7

chlorobenzene

cyclohexane
110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen; Leuna-Kontakt 6525 at 150℃; Product distribution; other halogen organic compounds, var. catalysts;100%
With hydrogen; platinum at 120℃; under 16501.7 Torr; for 1.66667h; Autoclave; Inert atmosphere;12.8%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; hydrogen; triethylamine In isopropyl alcohol at 75℃; under 31028.9 Torr; for 4h; other chloroaromatics; var. reaction time; catalytic hydrodechlorination;
chlorobenzene
108-90-7

chlorobenzene

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

1,2-diphenylpropan-1-one
2042-85-5

1,2-diphenylpropan-1-one

Conditions
ConditionsYield
With sodium t-butanolate; (SIPr)Pd(allyl)Cl In tetrahydrofuran at 70℃; for 1h; Product distribution; Further Variations:; Catalysts;100%
With potassium tert-butylate; C41H50ClN3Pd In tetrahydrofuran at 80℃; for 4h; Reagent/catalyst; Inert atmosphere;99%
With sodium t-butanolate; N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene-acetylacetonate palladium chloride In toluene at 60℃; for 1h;98%
chlorobenzene
108-90-7

chlorobenzene

benzylamine
100-46-9

benzylamine

N-Benzylaniline
758640-21-0

N-Benzylaniline

Conditions
ConditionsYield
With (55)Pd068(44)Ni032; potassium carbonate In water at 80℃; for 8h; Catalytic behavior; Buchwald-Hartwig Coupling;100%
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 48h;99%
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 48h;99%
9-phenyl-fluoren-9-ol
25603-67-2

9-phenyl-fluoren-9-ol

chlorobenzene
108-90-7

chlorobenzene

phenyl-[1,1';2',1'']terphenyl-2-yl-methanone
377092-23-4

phenyl-[1,1';2',1'']terphenyl-2-yl-methanone

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In o-xylene for 4h; Heating;100%
chlorobenzene
108-90-7

chlorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4-chlorophenylboronic acid pinacol ester
195062-61-4

4-chlorophenylboronic acid pinacol ester

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In chlorobenzene byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In chlorobenzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
chlorobenzene
108-90-7

chlorobenzene

potassium ferrocyanide

potassium ferrocyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;100%
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.166667h; Microwave irradiation;94%
With sodium carbonate; palladium diacetate; tri-tert-butyl phosphine In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;88%
2-phenylpyridine
1008-89-5

2-phenylpyridine

chlorobenzene
108-90-7

chlorobenzene

2-(biphenyl-2-yl)pyridine
219843-48-8

2-(biphenyl-2-yl)pyridine

Conditions
ConditionsYield
With dichloro[1-(3-methylbenzyl)-3-(n-butyl)benzimidazol-2-ylidene]ruthenium(II); potassium acetate In water at 100℃; for 1h; Reagent/catalyst;100%
With rhodium(III) chloride hydrate; sodium carbonate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 140℃; for 22h; Inert atmosphere;99%
With C36H35Cl2PRu; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; regioselective reaction;87%
C68H84N4Ni2

C68H84N4Ni2

chlorobenzene
108-90-7

chlorobenzene

A

(μ-Cl)2Ni2(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)2

(μ-Cl)2Ni2(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)2

B

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

C

4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 21h;A 100%
B n/a
C n/a
C23H40O7Si2

C23H40O7Si2

chlorobenzene
108-90-7

chlorobenzene

C22H40O5Si2

C22H40O5Si2

Conditions
ConditionsYield
at 140℃; for 1h; Microwave irradiation;100%
filgotinib hydrochloride

filgotinib hydrochloride

chlorobenzene
108-90-7

chlorobenzene

filgotinib chlorobenzene

filgotinib chlorobenzene

Conditions
ConditionsYield
Stage #1: filgotinib hydrochloride; chlorobenzene at 20℃; for 0.166667h;
Stage #2: With sodium hydroxide In water at 5℃; for 32h;
100%
bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(I) chloride

bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(I) chloride

chlorobenzene
108-90-7

chlorobenzene

bis(1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(dichloro)nickel

bis(1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(dichloro)nickel

Conditions
ConditionsYield
In benzene-d6 for 2h; Irradiation;100%
Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

Methyltrimethoxysilan
1185-55-3

Methyltrimethoxysilan

chlorobenzene
108-90-7

chlorobenzene

dimethoxy(methyl)phenylsilane
3027-21-2

dimethoxy(methyl)phenylsilane

Conditions
ConditionsYield
Stage #1: Methyltrimethoxysilan; chlorobenzene With magnesium In tetrahydrofuran for 1h; Reflux;
Stage #2: Methyltrichlorosilane; Methyltrimethoxysilan; chlorobenzene In tetrahydrofuran for 6.5h; Concentration; Reflux;
99.6%
acetamide
60-35-5

acetamide

chlorobenzene
108-90-7

chlorobenzene

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 18h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Time; Inert atmosphere; Sonication;99.1%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium carbonate In 1,4-dioxane at 90℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox;80%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 48h; Ullmann condensation;33%
With copper(l) iodide; potassium carbonate; pipecolic Acid In N,N-dimethyl-formamide at 110℃; for 30h; Goldberg coupling reaction;24%
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sonication;
acetyl chloride
75-36-5

acetyl chloride

chlorobenzene
108-90-7

chlorobenzene

para-chloroacetophenone
99-91-2

para-chloroacetophenone

Conditions
ConditionsYield
With zinc at 65 - 68℃; for 0.00833333h; Friedel-Crafts acylation; microwave irradiation;99%
With iron(III) oxide at 20℃; for 0.0833333h; Friedel Crafts acylation; regioselective reaction;95%
With zinc(II) oxide at 20℃; for 0.166667h; Friedel-Crafts acylation;87%
aniline
62-53-3

aniline

chlorobenzene
108-90-7

chlorobenzene

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; Ni(PPh3)2(1-(p-acetylnaphthyl))Cl In 1,4-dioxane at 100℃;99%
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere;99%
With sodium t-butanolate In toluene at 110℃; Inert atmosphere; Glovebox; chemoselective reaction;99%
4-Phenylphenol
92-69-3

4-Phenylphenol

chlorobenzene
108-90-7

chlorobenzene

4-Phenoxybiphenyl
3933-94-6

4-Phenoxybiphenyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;99%
With potassium hydroxide; copper at 375 - 400℃;

108-90-7Related news

Immobilized palladium-catalyzed electro-Fenton's degradation of Chlorobenzene (cas 108-90-7) in groundwater08/21/2019

This study investigates the effect of palladium (Pd) form on the electrochemical degradation of chlorobenzene in groundwater by palladium-catalyzed electro-Fenton (EF) reaction. In batch and flow-through column reactors, EF was initiated via in-situ electrochemical formation of hydrogen peroxide...detailed

Research paperMultichannel dissociation of physisorbed Chlorobenzene (cas 108-90-7) by KrF laser radiation08/20/2019

The photochemistry in adsorbed molecules is drastically different from that of gaseous ones. Seven channels of KrF laser-induced dissociation of chlorobenzene condensed on silica have been found using mass spectrometry. They include the multiple photon detachment of H and Cl atoms and the openin...detailed

A study of Chlorobenzene (cas 108-90-7) pyrolysis08/19/2019

The pyrolysis of chlorobenzene under dilute atmosphere and quasi-atmospheric pressure was studied at temperatures from 800 to 1150 K using a fused silica jet stirred reactor (JSR) and from 800 to 1250 K in an alumina tubular reactor. Chlorobenzene was chosen as a surrogate to model the thermal d...detailed

108-90-7Relevant articles and documents

Synergistic Activities in the Ullmann Coupling of Chloroarenes at Ambient Temperature by Pd-Supported Calcined Ferrocenated La2O3

Chumkaeo, Peerapong,Poonsawat, Thinnaphat,Meechai, Titiya,Somsook, Ekasith

, (2019)

Novel palladium-doped nanoparticles have been explored to serve as the first metal oxide-derived heterogeneous catalyst for Ullmann reaction of chloroarenes under mild condition (34?°C). This heterogeneous catalyst exhibited high catalytic activity towards the Ullmann homocoupling of chloroarenes into a series of useful symmetrically biaryl products with good to excellent yields in the presence of ethanol and NaOH, thereby leading to green and economical Ullmann reaction. The produced nanoparticles were successfully characterized by various techniques including PXRD, XPS, HRTEM, SEM-EDS, BET, TGA techniques, elemental mapping analysis and ICP-OES. Interestingly, based on characterization and experimental data, a reasonable mechanism has been proposed. Also, the formation of aryl methyl ketone as a by-product has been further confirmed by isotopic labelling experiments that the acetyl moiety is derived from ethanol. Moreover, the catalyst was stable and could be easily reused up to 5 times under atmospheric air without suffering significant loss in catalytic activity.

A Zn4L6 Capsule with Enhanced Catalytic C?C Bond Formation Activity upon C60 Binding

Lu, Zhenpin,Lavendomme, Roy,Burghaus, Olaf,Nitschke, Jonathan R.

, p. 9073 - 9077 (2019)

A redox-switchable self-assembled ZnII4L6 cage was synthesized that contains naphthalenediimide (NDI) motifs. Its reduction lent these NDI panels persistent radical anion character. The redox activity of this cage allows it to act as a catalyst for the oxidative coupling of different tetraaryl borates to give biaryls. The catalytic activity of the cage was enhanced following its binding of C60, which implies a mechanism that does not involve encapsulation of the substrate.

-

Bost, R. W.,Borgstrom, P.

, p. 1922 - 1925 (1929)

-

Kinetic study of the reactions of chlorine atoms and Cl2·- radical anions in aqueous : Solutions. 1. Reaction with benzene

Martire,Bertolotti,Braun,Gonzalez,Alegre,Gerones,Rosso

, p. 3117 - 3125 (2000)

The photolysis of NaS2O8 aqueous solutions containing Cl- ions is a clean technique for kinetic studies of the species Cl./Cl2.- in the presence and absence of added aromatic substrates. Laser and conventional flash-photolysis methods were used to study the aqueous phase reactions of chlorine atoms and Cl2.- (340 nm) radical ions in the presence and absence of benzene. A mechanism that considers the decay of Cl2.- in aqueous solutions with chloride ion concentrations from 1 x 10-4 to 0.6 M, total radical (Cl. + Cl2.-) concentrations at (0.1-1.5) x 10-5 M, and 2.5-3 pH was proposed. Kinetic computer simulations supported interpretation of the experimental data. The rate constants 6 x 109/M-sec ≤ k ≤ 1.2 x 1010/M-sec and 5/M-sec were determined for the reactions of Cl. and Cl2.-, respectively, in the aqueous phase. The organic radicals produced from these reactions showed an absorption band with maximum at 300 nm that was assigned to a Cl-cyclohexadienyl radical (Cl-CHD). The kinetic analysis of the traces supported a reversible reaction between Cl-CHD and O2. A reaction mechanism leading to the formation of chlorobenzene was proposed.

Application of a dioxo-molybdenum(VI) complex anchored on TiO2 for the photochemical oxidative decomposition of 1-chloro-4-ethylbenzene under O2

Bakhtchadjian, Robert,Tsarukyan, Samvel,Barrault, Joel,Martinez, Fernando O.,Tavadyan, Levon,Castellanos, Nelson J.

, p. 897 - 900 (2011)

The catalytic activity of dioxo-molybdenum(VI)- dichloro[4,4'- dicarboxylato-2,2'-bipyridine] covalently anchored through the carboxylate function to the surface of TiO2 has been tested for the oxidative degradation of 1-chloro-4- ethylbenzene in MeCN solution under argon and UV irradiation (λ = 254 nm). After 4-5 h of photochemical reaction, the Mo complex was reoxidized in the presence of O2 in the dark, and then the reaction was continued under argon. The reaction proceeds by the intermediate formation of 40-chloroacetophenone that undergoes further decomposition to chlorobenzene, plus small amounts of oxygen-containing organochlorine compounds, CO2 and H2O. Similar results were obtained for the decomposition of 4'-chloroacetophenone under the same conditions, which also gave chlorobenzene as one of the main products. The ratio of [final product]/ [Mo complex] increases during the decomposition of 1-chloro-4-ethylbenzene (up to 350-400% for 30-35 h of reaction), which provides evidence of a catalytic process. The probable photochemical reactions are discussed. Springer Science+Business Media B.V. 2011.

Oxychlorination and combustion of propene on fly-ash. Formation of chlorinated benzenes, dibenzodioxines and mono- and dibenzofurans

Jarmohamed, W.,Mulder, P.

, p. 1911 - 1918 (1994)

Heterogenous gas phase reactions of propene on fly ash in the presence of hydrochloric acid and air between 300-580 deg C have been investigated. At mild conditions only the formation of polychlorinated C1, C2 and C3 species takes place. At the high tempe

-

Le Fevre

, p. 1745,1746 (1932)

-

Transformation of chemical contaminants by biotic and abiotic processes in water and soil

Mansour,Feicht

, p. 323 - 332 (1994)

In contrast to biological processes, which can give rise to only a limited amount of transformation because of the biostability of many persistent organic chemicals, abiotic environmental factors (solar radiation) make an appreciable contribution to the transformation of these substances in the environment. In this context, abiotic transformation of organic chemicals should be investigated with particular consideration to the dynamic and catalytic effects due primarily to the state of the molecule and its interaction with the environment. Our investigation demonstrate that selected chemical substances can be degraded and mineralized within relatively short periods if irradiated with light of wavelenghts λ ≥ 290 nm. The present investigations deals with the fate of selected s-triazines in soil and under simulated solar light in the presence of TiO2 and soil suspension.

Formation of complex organochlorine species in water due to cavitation

Kruus, Peeter,Beutel, Lise,Aranda, Rocio,Penchuk, Jaan,Otson, Rein

, p. 1811 - 1824 (1998)

Sonication at 900 kHz was carried out on aqueous solutions of chloroform in the concentration range 25 to 500 mg/L. The formation of chlorinated hydrocarbons was detected by means of GC/MS analyses. For instance, carbon tetrachloride, chlorinated ethanes, and chlorinated ethenes were formed after 10 min of sonication. The greatest concentration of any product was 6 mg/L. Sonication of aqueous chloroform with phenol present produced chlorophenols, and with benzene present produced phenol, chlorobenzene and chlorophenols. These results are significant for the evaluation of sonication as a method of eliminating chlorinated organic compounds from water. They also have significance in supporting the notion that some complex organochlorines may be formed naturally in the environment. Some chloroform and methyl chloride are produced in nature and could react with other organic compounds to form more complex organochlorines through natural processes which have an action similar to cavitation, e.g. waterfalls and breaking waves.

Catalytic alkane oxidation by homogeneous and silica-supported cobalt(II) complex catalysts with a triazoly group-containing tetradentate ligand

Nakazawa, Jun,Yata, Akinori,Hori, Tomoaki,Stack, T. Daniel P.,Naruta, Yoshinori,Hikichi, Shiro

, p. 1197 - 1199 (2013)

Homogeneous and heterogeneous cobalt complex catalysts with bis(pyridylmethyl)(triazolylmethyl)amine ligand were prepared. Although simple cobalt salts catalyze cyclohexane oxidation with mCPBA, the cyclohexane selectivity increases upon coordination of tetradentate ligands. In the heterogeneous catalysis, the yield and selectivity of cyclohexanol are improved with an increase in the ligand density on the silica support due to the suppression of metal leaching.

Liquid-Phase Hydrogenation of Halobenzenes in the Presence of Palladium-Containing Nanodiamonds

Kalmykov,Magdalinova,Klyuev

, p. 1206 - 1212 (2018)

Abstract: The catalytic activity of palladium-containing nanodiamonds (Pd/ND) is studied in the model reaction of liquid-phase hydrodehalogenation of monohalobenzenes (chlorobenzene, bromobenzene, and iodobenzene) and ortho-, meta-, and para-isomers of dichlorobenzene under mild conditions (Т = 45°С, (Formula presented.)?= 1 atm). The obtained results are compared with the catalytic behavior of the palladium-containing activated carbon (Pd/C) under identical conditions. It is found that catalyst Pd/ND is more active than Pd/C and is more stable against the poisonous effect of hydrogen halide forming during the reaction. Study of the effect of HCl and NaOH additives on the catalyst activity shows that, in the presence of HCl, poisoning of the catalyst occurs: the rate of reaction decreases; in the presence of NaOH, the catalyst activity grows; the rate of reaction increases as a result of hydrogen chloride neutralization by an alkali. For both catalysts the rate of reaction decreases in the sequence Cl > Br > I for monohalobenzenes and in the sequence para- > ortho- > meta-isomer in the case of dichlorobenzenes. The obtained dependences are explained using the quantum-chemical modeling of substrates of model reactions.

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Baird et al.

, p. 1173 (1969)

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-

Erickson et al.

, p. 461 (1966)

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Oxidative radical arylation of anilines with arylhydrazines and dioxygen from air

Hofmann, Josefa,Jasch, Hannelore,Heinrich, Markus R.

, p. 2314 - 2320 (2014)

Substituted 2-aminobiphenyls have been prepared from arylhydrazine hydrochlorides and anilines in biphasic radical arylation reactions with dioxygen from air as a most simple and readily available oxidant. Under optimized conditions, the free amino functionality of the aniline leads to high ortho:meta regioselectivities, now even for anilines bearing a donor substituent in the para position. Finally, the mild and metal-free new access to aminobiphenyls was shown to be applicable on a gram scale.

Molecule-induced homolysis of N-hydroxyphthalimide (NHPI) by peracids and dioxirane. A new, simple, selective aerobic radical epoxidation of alkenes

Minisci, Francesco,Gambarotti, Cristian,Pierini, Monica,Porta, Ombretta,Punta, Carlo,Recupero, Francesco,Lucarini, Marco,Mugnaini, Veronica

, p. 1421 - 1424 (2006)

Evidences are reported concerning the molecule-induced homolysis of NHPI by peracids and dioxirane; their combination can be utilized for the aerobic free-radical epoxidation of alkenes with selectivity quite different from the well-known epoxidation by peracids.

Hazardous air pollutants formation from reactions of raw meal organics in cement kilns

Sidhu, Sukh,Kasti, Nabil,Edwards, Phil,Dellinger, Barry

, p. 499 - 506 (2001)

Thermally induced chlorination, condensation, and formation reactions of raw meal organic surrogates were investigated on different types of surfaces. The System for Thermal Diagnostic Studies provided a powerful tool to study these reactions under defined reaction conditions, which were related to typical conditions in the preheater zone of cement kiln. Experiments were conducted with benzene and benzene/myristic acid (C6H6/C13H27COOH) mixtures in a quartz reactor containing different chlorinating catalysts/reagents over a temperature range of 300-500°C. Reaction products were trapped in-line and analyzed by GC-MS. A mixture of chlorides of calcium, potassium, aluminium and iron was highly effective for chlorination/condensation reactions of benzene and benzene/myristic acid mix at temperatures above 300°C. The same behavior was observed only when calcium chloride and potassium chloride were used as chlorinating catalyst/reagent. This result showed that transition metal chlorides like FeCl3 are not necessary for chlorination/condensation of organics under post-combustion conditions. Methylene chloride was the major chlorinated product followed by chloroform and various other C1, C2 and C6 chlorinated products. Yields of chlorinated aliphatics were highest at 400°C for both benzene and benzene/myristic acid mix. C6 products were mainly mono- to hexa-chlorinated benzenes with trace amounts of chlorinated phenols. The major chlorinated products observed in this study (i.e., methylene chloride, chloroform, chloroethanes and monochlorobenzene) were also present as major chlorinated hydrocarbons in the cement kiln field emission data.

Synthesis and spectral properties of iron(III) tetra-tert-butylphthalocyanine complexes

Burtsev, Ivan D.,Dubinina, Tatiana V.,Platonova, Yana B.,Kosov, Anton D.,Pankratov, Denis A.,Tomilova, Larisa G.

, p. 466 - 469 (2017)

Two tetra-tert-butylphthalocyanine complexes of iron(III) were synthesized in high yields from the phthalocyanine ligand and iron(III) salts; the oxidation state of iron was confirmed by M?ssbauer and EPR spectroscopy. The existence of an acid–base equilibrium during spectrophotometric titration was revealed. The ButPcFeCl complex catalyzed chlorination of benzene.

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Beringer,Bodlaender

, p. 1981 (1969)

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Kinetics and mechanism of the reaction of Cl atoms with nitrobenzene

Froosig,Nielsen,Bilde,Wallington,Orlando,Tyndall

, p. 11328 - 11331 (2000)

The kinetics and mechanism of the reaction of Cl atoms with nitrobenzene in 10-700 torr of N2, or air, at 296 K were studied using smog chamber/FTIR methods. The reaction of Cl atoms with nitrobenzene proceeded with a rate constant of 9.3 × 10-13 cc/molecule-sec to give C6H5Cl and NO2 products in essentially 100% yield. The UV-visible spectrum of nitrobenzene was measured. The dominant atmospheric fate of nitrobenzene was photolysis, which occurred at a rate of 3 × 10-5/sec for a solar zenith angle of 25° representative of a typical summer day at 40°N.

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Jenner

, p. 1031 (1962)

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Kochi

, p. 2500,2501 (1965)

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Ichikawa et al.

, p. 169 (1971)

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Erlenmeyer,Leo

, p. 897,903 (1933)

The importance of copper placement in chiral catalysts supported on heteropolyanions: Lacunary vs external exchanged

Fraile, José M.,Mansilla, Daniela S.,Mayoral, José A.,Torviso, M. Rosario

, (2020)

Lacunary [PCuW11O39]5? species modified with chiral bis(oxazoline) leads to very poor results as catalyst in the enantioselective cyclopropanation, in contrast with the Cu-bis(oxazoline) complex exchanged on the Keggin [PW12O40]3? species. The incomplete neutralization and/or exchange of the Keggin species produces a loss in symmetry that leads to spectra in solid phase (IR and NMR) similar to those obtained for the lacunary species. The symmetry is averaged in solution, but additional characterization methods are necessary to determine the true nature of the solid heteropolyanionic species. These results demonstrate that the efficiency of copper-bis(oxazoline) complexes is related to its placement in an external exchange position, whereas the copper included in the heteropolyanion structure is not active for cyclopropanation reactions.

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Milligan et al.

, p. 158,161 (1962)

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Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

Nannapaneni, Madhavi,Pendem, Venkata Bhavanarushi,Tamminana, Ramana

, (2022/01/12)

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

Homogeneous oxidation of C–H bonds with m-CPBA catalysed by a Co/Fe system: mechanistic insights from the point of view of the oxidant

Kuznetsov, Maxim L.,Nesterov, Dmytro S.,Nesterova, Oksana V.,Pombeiro, Armando J. L.,Shul'pin, Georgiy B.

, p. 282 - 299 (2022/01/19)

Oxidations of C–H bonds with m-chloroperoxybenzoic acid (m-CPBA) catalyzed by transition metal complexes are known to proceed through a number of routes, from the non-selective free radical to selective concerted and metal-mediated ones. However, there is a lack of understanding of the m-CPBA oxidative behavior, reaction mechanisms and factors that trigger its activity. An experimental and theoretical investigation of sp3 C–H bond oxidation with m-CPBA in the presence of the heterometallic pre-catalyst [CoIII4FeIII2O(Sae)8]·4DMF·H2O (1) (H2Sae = salicylidene-2-ethanolamine) and HNO3 promoter has been performed herein. The catalytic system 1/HNO3/m-CPBA allows mild hydroxylation of tertiary C–H bonds with 99% retention of stereoconfiguration of model alkane substrates, supported by high TOFs up to 2 s?1 (for cis-1,2-dimethylcyclohexane) and TONs up to 1.4 × 104 (at 50 °C). The catalytic effect of 1 is seen at the ppm level, while 1000 ppm (0.1 mol%) loading allows 1000-fold increase of the initial reaction rate up to 9 × 10?5 M s?1. The reaction mechanism was investigated by means of combined kinetic studies (including isotope effects), isotopic labeling (18O2, H218O, D2O), ESI-MS spectroscopy and DFT theoretical studies. The results suggest that the main oxidation pathway proceeds through a concerted mechanism involving a cobalt-peroxo C–H attacking species or via a cobalt–oxyl species (rebound process), rather than a free-radical pathway. Remarkably, the Co(iii) catalyst does not change its oxidation state during the most energetically favored pathway, consistent with a metal–ligand cooperativity. The chlorobenzene radical is responsible for H abstraction in the non-selective side route, which is efficiently suppressed by the acidic promoter. Finally, signs for slow direct oxygen exchange between m-CPBA and water in the presence of a proton or a metal complex are found, suggesting that the results of 18O-tests should be treated cautiously when m-CPBA is used as the oxidant.

Photoredox-catalyzed reduction of halogenated arenes in water by amphiphilic polymeric nanoparticles

Eisenreich, Fabian,Kuster, Tom H. R.,Palmans, Anja R. A.,van Krimpen, David

supporting information, (2021/10/05)

The use of organic photoredox catalysts provides new ways to perform metal-free reactions controlled by light. While these reactions are usually performed in organic media, the application of these catalysts at ambient temperatures in aqueous media is of considerable interest. We here compare the activity of two established organic photoredox catalysts, one based on 10-phenylphenothiazine (PTH) and one based on an acridinium dye (ACR), in the light-activated dehalogenation of aromatic halides in pure water. Both PTH and ACR were covalently attached to amphiphilic polymers that are designed to form polymeric nanoparticles with hydrodynamic diameter DH ranging between 5 and 11 nm in aqueous solution. Due to the hydrophobic side groups that furnish the interior of these nanoparticles after hydrophobic collapse, water-insoluble reagents can gather within the nanoparticles at high local catalyst and substrate concentrations. We evaluated six different amphiphilic polymeric nanoparticles to assess the effect of polymer length, catalyst loading and nature of the catalyst (PTH or ACR) in the dechlorination of a range of aromatic chlorides. In addition, we investigate the selectivity of both catalysts for reducing different types of aryl-halogen bonds present in one molecule, as well as the activity of the catalysts for C-C cross-coupling reactions. We find that all polymer-based catalysts show high activity for the reduction of electron-poor aromatic compounds. For electron-rich compounds, the ACR-based catalyst is more effective than PTH. In the selective dehalogenation reactions, the order of bond stability is C-Cl > C-Br > C-I irrespective of the catalyst applied. All in all, both water-compatible systems show good activity in water, with ACR-based catalysts being slightly more efficient for more resilient substrates.

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