Chlorobenzene
| Names | |
|---|---|
| IUPAC name
Chlorobenzene
| |
| Preferred IUPAC name
Chlorobenzene | |
| Systematic IUPAC name
Chlorobenzene | |
| Other names
1-Chlorobenzene
Benzene chloride Monochlorobenzene Phenyl chloride | |
| Properties | |
| C6H5Cl | |
| Molar mass | 112.56 g/mol |
| Appearance | Colorless liquid |
| Odor | Almond-like |
| Density | 1.11 g/cm3 (20 °C) |
| Melting point | −45 °C (−49 °F; 228 K) |
| Boiling point | 131 °C (268 °F; 404 K) |
| 0.05 g/100 ml (20 °C) | |
| Solubility | Miscible with alcohols, ethers, halocarbons, hydrocarbons |
| Vapor pressure | 8.8 mmHg at 20 °C |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 29 °C (84 °F; 302 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
2290 mg/kg (rat, oral) 2250 mg/kg (rabbit, oral) 2300 mg/kg (mouse, oral) 2250 mg/kg (guinea pig, oral) |
| Related compounds | |
| Related compounds
|
Benzene 1,4-Dichlorobenzene Fluorobenzene Bromobenzene Iodobenzene |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl.
Contents
Properties
Chemical
Chlorobenzene reacts with molten NaOH at 350 °C to yield phenol:
- C6H5Cl + NaOH → C6H5OH + NaCl
The reaction is known as the Dow process.
Physical
Chlorobenzene is a colorless liquid, immiscible with water but miscible with most organic solvents.
Availability
Chlorobenzene is sold by chemical suppliers.
Preparation
Chlorobenzene is manufactured by chlorination of benzene in the presence of a catalytic amount of Lewis acid such as anhydrous ferric chloride or aluminium chloride, or even sulfur dichloride.
- C6H5 + Cl2 → C6H5Cl + HCl
TCCA and NaDCCA can also be substituted for chlorine and ferric chloride. Several SM hobby chemists have managed to prepared chlorobenzene via this route.[1]
Chlorobenzene can also be produced from aniline via benzenediazonium chloride, otherwise known as the Sandmeyer reaction. SM user ParadoxChem126 made ~9 ml of chlorobenzene via this route, which corresponds to an yield of 40%.
Projects
- Make phenylmagnesium chloride (Grignard reactions)
Handling
Safety
Chlorobenzene is considered to have low to moderate toxicity, although it is still an irritant and ingestion may cause serious harm.
Chlorobenzene can persist in soil for several months, in air for about 3.5 days, and in water for less than one day.
Storage
In closed glass bottles with a proper lid.
Disposal
Controlled incineration in a special incinerator is used to destroy the compound.
Alternatively, a solution of Fenton's reagent can be used to neutralize small amounts of chlorobenzene.
The bacterium Rhodococcus phenolicus degrades chlorobenzene as sole carbon sources.[2]
References
- ↑ https://www.youtube.com/watch?v=IMFWT_2pWLw
- ↑ https://www.sciencedirect.com/science/article/abs/pii/S0723202005000986?via%3Dihub
