|Jmol-3D images||Image 1|
|Molar mass||76.52 g mol−1|
|Melting point||−135 °C (−211 °F; 138 K)|
|Boiling point||45 °C (113 °F; 318 K)|
|Solubility in water||0.36 g/100 mL (20 °C)|
|Solubility||soluble in ether, acetone, benzene, chloroform|
|Refractive index (nD)||1.4055|
|EU classification||Flammable (F)
Carc. Cat. 3
Muta. Cat. 3
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|
|Flash point||−32 °C (−26 °F; 241 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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.
Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting phosphorus trichloride with allyl alcohol. 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 are produced in this way in 1997.
Reactions and uses
The great majority of allyl chloride is converted to epichlorohydrin. Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil) 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), reductive coupling to give diallyl, oxidative addition to palladium to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2, and dehydrohalogenation to cyclopropene.
- International Chemical Safety Card 0010
- NIOSH Pocket Guide to Chemical Hazards 0018
- IARC Monograph *Allyl chloride.
- 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.
- J. V. Supniewski and P. L. Salzberg (1941), "Allyl Cyanide", Org. Synth.; Coll. Vol. 1: 46
- International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.