Chlorobenzene

Base Information

• Chemical Name: Chlorobenzene
• CAS No.: 108-90-7
• Deprecated CAS: 50717-45-8
• Molecular Formula: C6H5Cl
• Molecular Weight: 112.559
• Hs Code.: 29039190
• European Community (EC) Number: 203-628-5,270-127-6
• ICSC Number: 0642
• NSC Number: 8433
• UN Number: 1134
• UNII: K18102WN1G
• DSSTox Substance ID: DTXSID4020298
• Nikkaji Number: J2.869J
• Wikipedia: Chlorobenzene
• Wikidata: Q407768
• Metabolomics Workbench ID: 49581
• ChEMBL ID: CHEMBL16200
• Mol file: 108-90-7.mol

Synonyms:chlorobenzene;monochlorobenzene

Chemical Property of Chlorobenzene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 11.8 mm Hg ( 25 °C)
• Melting Point: -45 °C
• Refractive Index: n20/D 1.524(lit.)
• Boiling Point: 131 °C
• Flash Point: 29 °C
• PSA: 0.00000
• Density: 1.1075 g/cm³
• LogP: 2.34000
• Storage Temp.: 0-6°C
• Solubility.: water: soluble0.207 g/L at 20°C
• Water Solubility.: 0.4 g/L (20 ºC)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 112.0079779
• Heavy Atom Count: 7
• Complexity: 46.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Chlorobenzene min. 98.0 % ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T,F
• Hazard Codes: Xn,N,T,F
• Statements: 10-20-51/53-40-39/23/24/25-23/24/25-11
• Safety Statements: 24/25-61-36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Chlorinated Aromatics
• Canonical SMILES: C1=CC=C(C=C1)Cl
• Recent ClinicalTrials: To Evaluate the Effect of Chlorhexidine-benzidamine Administration
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system. This may result in lowering of consciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the liver and kidneys.
• 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: 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. 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.
• 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).

Technology Process of Chlorobenzene

There total 877 articles about Chlorobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

2-iodochlorobenzene (615-41-8) → chlorobenzene (108-90-7) + 2,2'-Dichlorobiphenyl (13029-08-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 2-pentanol; at 100 ℃; for 36h; Inert atmosphere;

DOI:10.1021/jo100089d

Reference yield: 62.0%

benzoin isopropyl ether (6652-28-4) + p-chlorobenzenediazonium tetrafluoroborate (673-41-6) → benzaldehyde (100-52-7) + chlorobenzene (108-90-7) + benzil (134-81-6)

Guidance literature:

In acetonitrile; Product distribution; Quantum yield; Irradiation; also with p-CH₃O-Ph-N₂BF₄ and without aryldiazonium salt as reaction partner, with and without O₂;

Reference yield: 40.0%

benzoin phenylhydrazone ethyl ether (64357-12-6) → benzoic acid ethyl ester (93-89-0,99341-95-4) + 2-ethoxy-1,2-diphenyl-ethanone (574-09-4) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7) + chlorobenzene (108-90-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With copper dichloride; for 5h; Product distribution; Heating; variation of time;

DOI:10.1021/jo00315a043

upstream raw materials:

N-chloropiperidine

diethyl ether

quinoline

(+/-)-1r,2t-dibromo-1-chloro-cyclohexane

Downstream raw materials:

N-phenyl piperidine

α-naphthol

phosgene

oxalyl dichloride

Refernces

• 1、 Yang, Cangming,Pittman Jr., Charles U.. "Dechlorination of pentachlorophenol and 1,2,4-trichlorobenzene using NaBH4 and NaBH4/LiCl at 125-315°C in glyme solvents". . p. 517 - 525. Retrieved 1998.
• 2、 Nakano,Kawasaki,Ponomarev,Hurley,Wallington. "Kinetics and mechanism of the gas phase reaction of Cl atoms and OH radicals with bromobenzene". . p. 77 - 83. Retrieved 2002.
• 3、 Nakazawa, Jun,Hori, Tomoaki,Stack, T. Daniel P.,Hikichi, Shiro. "Alkane oxidation by an immobilized nickel complex catalyst: Structural and reactivity differences induced by surface-ligand density on mesoporous silica". . p. 1191 - 1199. Retrieved 2013.
• 4、 Kesselmayer, Mark A.,Sheridan, Robert S.. "Phenoxychlorocarbene. Spectroscopy and Photochemical Interconversion of Geometric Isomers". . p. 844 - 845. Retrieved 1986.
• 5、 Li, Yaming,Chen, Tao,Wang, Huifeng,Zhang, Rong,Jin, Kun,Wang, Xiuna,Duan, Chunying. "A ligand-free copper-catalyzed decarboxylative trifluoromethylation of aryliodides with sodium trifluoroacetate using Ag2O as a promoter". . p. 1713 - 1716. Retrieved 2011.
• 6、 Puy, Michael van der. "CONVERSION OF DIARYLIODONIUM SALTS TO ARYL FLUORIDES". . p. 385 - 392. Retrieved 1982.
• 7、 Hardy,Fortenbaugh. "". . p. 1716. Retrieved 1958.
• 8、 Yoshida, Masato,Furuta, Naoki,Kobayashi, Michio. "CIDNP Studies of the Thermal Decomposition of Arylazo Aryl Sulfones". . p. 2356 - 2359. Retrieved 1981.
• 9、 Hassani, Aydin,Khataee, Alireza,Karaca, Semra. "Photocatalytic degradation of ciprofloxacin by synthesized TiO2 nanoparticles on montmorillonite: Effect of operation parameters and artificial neural network modeling". . p. 149 - 161. Retrieved 2015.
• 10、 Boudakian, Max M.,Hyde, Gene A.. "SUBSTITUTIVE AROMATIC FLUORINATION WITH CHLORINE PENTAFLUORIDE". . p. 435 - 446. Retrieved 1984.