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

Synthesis of 10-(Hydroxymethyl)-7,12-dimethylbenzanthracene

10.1021/jo00359a058

The research involves the synthesis of various organic compounds. The first part focuses on the synthesis of a keto ester and a bicyclic keto lactam. The key chemicals used include ketene O,S-acetals, p-TsOH, methylamine, and silica gel for purification. The second part describes the synthesis of 10-(hydroxymethyl)-7,12-dimethylbenz[a]anthracene, involving a series of reactions starting from 1,2-naphthalic anhydride and chlorobenzene, with reagents such as AlCl?, NaBH?, Zn, KOH, and others playing crucial roles. The final part reports the synthesis of gem-dilithiofluorene by thermal rearrangement of 9-lithiofluorene, with n-butyllithium and fluorene as the starting materials. The research highlights the use of various solvents like THF, benzene, and ethyl acetate, and purification techniques such as chromatography and recrystallization.

Direct Aromatic Periodination

10.1021/jo00191a003

The study explores a direct method for the periodination of aromatic compounds using periodic acid (HIO?) and iodine in concentrated sulfuric acid. This method allows for the exhaustive iodination of unactivated aromatic substrates such as benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene, converting them into their respective periodo derivatives. The study also reports the conversion of benzonitrile to pentaiodobenzamide. The direct periodination method is compared favorably to the existing mercuration/iododemercuration sequence in terms of reaction time and purity of products. The study highlights the versatility of the method, demonstrating that partially iodinated products can be obtained under less vigorous conditions. Additionally, the study discusses the limitations of the method, noting that certain activated aromatics and easily oxidized substrates do not fare well under these conditions. The research provides detailed experimental procedures and characterizations of the synthesized compounds, contributing to the field of organic chemistry by offering a more efficient route for the preparation of polyiodinated and periodinated aromatic compounds.