Chlorobenzene
| Chlorobenzene | |
|---|---|
| chlorobenzene | |
| Other names benzene chloride monochlorobenzene Phenyl chloride | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 108-90-7 
|
| PubChem | 7964 |
| ChemSpider | 7676 |
| RTECS number | CZ0175000 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | MVPPADPHJFYWMZ-UHFFFAOYAG |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C6H5Cl |
| Molar mass | 112.56 g/mol |
| Appearance | colorless liquid |
| Density | 1.11 g/cm³, liquid |
| Melting point |
-45 °C, 228 K, -49 °F |
| Boiling point |
131 °C, 404 K, 268 °F |
| Solubility in water | low |
| Solubility in other solvents | soluble in most organic solvents |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| R-phrases | R10 R20 R51/53 |
| S-phrases | S24/25 S61 |
| NFPA 704 | |
| Flash point | 29 °C |
| style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds | |
| Related Halobenzenes | Fluorobenzene Bromobenzene Iodobenzene |
| Related compounds | benzene 1,4-dichlorobenzene |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
Contents
Uses
Chlorobenzene once was used in the manufacture of certain pesticides, most notably DDT by reaction with chloral (trichloroacetaldehyde), but this application has declined with the diminished use of DDT. At one time, chlorobenzene was the main precursor for the manufacture of phenol:[1]
- C6H5Cl + NaOH → C6H5OH + NaCl
The major use of chlorobenzene is as an intermediate in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in many industrial applications as well as in the laboratory.[2] Chlorobenzene is nitrated on a large scale to give a mixture of 2- and 4-nitrochlorobenzenes, which can be separated by fractional crystallization followed by distillation. 2-Nitrochlorobenzene (CAS#88-73-3) is converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitropaniline by nucleophilic displacement of the chloride with sodium hydroxide, sodium methoxide, sodium disulfide and ammonia. The conversion of the 4-nitrochlorobenzene (CAS#100-00-5) are similar.[3]
Synthesis
Chlorobenzene was first described in 1851. Presently it is manufactured by chlorination of benzene in the presence of a catalytic amount of Lewis acid such as ferric chloride and anhydrous aluminium chloride:
The catalyst enhances the electrophilicity of the chlorine. Because chlorine is electronegative, C6H5Cl exhibits decreased susceptibility to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.
Safety
Chlorobenzene exhibits "low to moderate" toxicity as indicated by its LD50 of 2.9 g/kg.[2]
References
- ↑ Manfred Weber, Markus Weber, Michael Kleine-Boymann, “Phenol” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a19 299.pub2
- ↑ 2.0 2.1 Manfred Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a06 233.pub2
- ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411
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