Allyl chloride

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Allyl chloride
Allyl chloride.svg
IUPAC name
Other names
107-05-1 YesY
ChEMBL ChEMBL451126 YesY
ChemSpider 13836674 YesY
EC number 209-675-8
Jmol-3D images Image
PubChem 7850
Molar mass 76.52 g·mol−1
Appearance Colorless, brown, yellow, or purple liquid[1]
Odor pungent, unpleasant[1]
Density 0.94 g/mL
Melting point −135 °C (−211 °F; 138 K)
Boiling point 45 °C (113 °F; 318 K)
0.36 g/100 mL (20 °C)
Solubility soluble in ether, acetone, benzene, chloroform
Vapor pressure 295 mmHg[1]
EU Index 602-029-00-X
EU classification Flammable (F)
Harmful (Xn)
Carc. Cat. 3
Muta. Cat. 3
Dangerous for
the environment (N)
R-phrases R11 R20/21/22 R36/37/38 R40 R40 R48/20 R68 R50
S-phrases (S2) S16 S25 S26 S36/37 S46 S61
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −32 °C (−26 °F; 241 K)
390 °C (734 °F; 663 K)
Explosive limits 2.9–11.2%
US health exposure limits (NIOSH):
TWA 1 ppm (3 mg/m3)[1]
TWA 1 ppm (3 mg/m3)
ST 2 ppm (6 mg/m3)[1]
250 ppm[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene.


Laboratory scale[edit]

Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride.[2] Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.[3]

Industrial scale[edit]

Today allyl chloride is prepared by the reaction of propylene with chlorine. At lower temperatures, the main product is 1,2-dichloropropane, but at 500 °C, allyl chloride predominates, being formed via a free radical reaction:

CH3CH=CH2 + Cl2 → ClCH2CH=CH2 + HCl

An estimated 800M Kg were produced this way in 1997.[2]

Reactions and uses[edit]

The great majority of allyl chloride is converted to epichlorohydrin.[2] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)[2] and allylsilane.

In the laboratory, allyl chloride is a common alkylating agent, useful in the manufacture of pharmaceuticals and pesticides. Illustrative of its reactivity include its cyanation to allyl cyanide (CH2=CHCH2CN),[4] reductive coupling to give diallyl, oxidative addition to palladium to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2, and dehydrohalogenation to cyclopropene.


Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[5]

See also[edit]

External links[edit]


  1. ^ a b c d e f g h "NIOSH Pocket Guide to Chemical Hazards #0018". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b c d Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000.
  3. ^ Furniss, Brian; Hannaford, Antony; Smith, Peter; and Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. p. 558. ISBN 9780582462366. 
  4. ^ J. V. Supniewski and P. L. Salzberg (1941). "Allyl Cyanide". Org. Synth. ; Coll. Vol. 1, p. 46 
  5. ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.