Chlorobenzene

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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):
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.

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

  1. https://www.youtube.com/watch?v=IMFWT_2pWLw
  2. https://www.sciencedirect.com/science/article/abs/pii/S0723202005000986?via%3Dihub

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