Chlorobenzene
From Wikipedia, the free encyclopedia
| Chlorobenzene | |
|---|---|
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| General | |
| Systematic name | chlorobenzene |
| Other names | benzene chloride monochlorobenzene Phenyl chloride |
| Molecular formula | C6H5Cl |
| SMILES | ClC1=CC=CC=C1 |
| Molar mass | 112.56 g/mol |
| Appearance | colorless liquid |
| CAS number | [108-90-7] |
| Properties | |
| Density and phase | 1.11 g/cm3, liquid |
| Solubility in water | low |
| Other solvents | most organic solvents |
| Melting point | -45 °C (228 K) |
| Boiling point | 131 °C (404 K) |
| Refractive index (nD20) | 1.525 |
| Viscosity | ? cP at ? °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | 29 °C |
| R/S statement | R: 10 20 51/53 S: 24/25 61 |
| RTECS number | CZ0175000 |
| Related compounds | |
| Related compounds | benzene 1,4-dichlorobenzene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. It is a colorless, flammable liquid first made in 1851 by reacting phenol and phosphorus pentachloride.[citation needed]
[edit] Uses
Chlorobenzene has been used in the manufacture of certain pesticides, most notably DDT by reaction with chloral (trichloroacetaldehyde). It once found use in the production of phenol. Today the major use of chlorobenzene is as an intermediate in the production of nitrochlorobenzenes and diphenyl oxide, which are important in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in organic synthesis as well as many industrial applications.
[edit] Synthesis
Chlorobenzene is prepared by chlorination of benzene, usually in the presence of a catalytic amount of Lewis acid such as ferric chloride:
- C6H6 + Cl2 → C6H5Cl + HCl
Because chlorine is electronegative, PhCl exhibits decreased susceptibility to to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.
