Chlorobenzene

Chlorobenzene
Chlorobenzene
Identifiers
CAS number 108-90-7 YesY
PubChem 7964
ChemSpider 7676 YesY
UNII K18102WN1G YesY
KEGG C06990 YesY
ChEBI CHEBI:28097 YesY
ChEMBL CHEMBL16200 YesY
RTECS number CZ0175000
Jmol-3D images Image 1
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
Hazards
MSDS External MSDS
R-phrases R10 R20 R51/53
S-phrases S24/25 S61
NFPA 704
NFPA 704.svg
3
3
0
Flash point 29 °C
Related compounds
Related Halobenzenes Fluorobenzene
Bromobenzene
Iodobenzene
Related compounds benzene
1,4-dichlorobenzene
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
 YesY (verify) (what is: YesY/N?)
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:

Chlorination benzene.svg

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]

Toxicology

Chlorobenzene is not a naturally occurring compound, but because of its manufacture, can persist in soil for several months, in air for about 3.5 days, and in water for less than one day. Humans may be exposed to this agent via breathing contaminated air (primarily via occupational exposure), eating contaminated food or water, or by coming into contact with contaminated soil (typically near hazardous waste sites). However, because it has only been found at 97 out of 1,177 NPL hazardous waste sites, it is not considered a widespread environmental contaminant.

Upon entering the body, typically via contaminated air, chlorobenzene is excreted both via the lungs and the urinary system.

References

  1. ^ 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. ^ a b Manfred Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a06 233.pub2
  3. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411

Wikimedia Foundation. 2010.

Нужно решить контрольную?

Look at other dictionaries:

  • Chlorobenzene — Chlorobenzène Chlorobenzène Général …   Wikipédia en Français

  • Chlorobenzène — Général …   Wikipédia en Français

  • chlorobenzène — ● chlorobenzène nom masculin Dérivé chloré du benzène C6H5Cl. (Il est employé comme solvant et comme intermédiaire dans la synthèse organique.) chlorobenzène [klɔʀobɛ̃zɛn] n. m. ÉTYM. 1869; de chloro , et benzène. ❖ ♦ Chim. Dérivé monochloré du… …   Encyclopédie Universelle

  • chlorobenzene — [klôr΄ō ben′zēn΄] n. a clear flammable liquid, C6H5Cl, used as a solvent for paints, lacquers, etc. and in organic synthesis …   English World dictionary

  • chlorobenzene — /klawr euh ben zeen, ben zeen , klohr /, n. a colorless, volatile, water insoluble, flammable liquid, C6H5Cl, having an almondlike odor, prepared from benzene by chlorination: used as a solvent for resins, paints, and lacquers, and in the… …   Universalium

  • chlorobenzene — chlorbenzenas statusas T sritis chemija formulė C₆H₅Cl atitikmenys: angl. chlorobenzene rus. хлорбензол …   Chemijos terminų aiškinamasis žodynas

  • Chlorobenzene (data page) — This page provides supplementary chemical data on Chlorobenzene. Contents 1 Material Safety Data Sheet 2 Structure and properties 3 Thermodynamic properties 4 V …   Wikipedia

  • chlorobenzene — noun Etymology: International Scientific Vocabulary Date: circa 1889 a colorless flammable volatile toxic liquid C6H5Cl used in organic synthesis (as of DDT) and as a solvent …   New Collegiate Dictionary

  • chlorobenzene — noun Any derivative of benzene in which one or more hydrogen atoms is replaced by chlorine; but especially the simplest such derivative CHCl that is used in the manufacture of phenol, aniline and other compounds …   Wiktionary

  • chlorobenzene — chlo·ro·benzene …   English syllables

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”