Allyl chloride

Allyl chloride
IUPAC name 1-Chloroprop-2-ene
Properties
Molecular formula	C3H5Cl
Molar mass	76.52 g mol−1
Density	0.94 g/mL
Melting point	-135 °C, 138 K, -211 °F
Boiling point	45 °C, 318 K, 113 °F
Solubility in water	0.36 g/100 mL (20 °C)
Hazards
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	3 3 1
Flash point	−32 °C
Autoignition temperature	390 °C
Explosive limits	2.9–11.2%
Y chloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Production

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 annually.^[1]

Reactions and uses

The great majority of allyl chloride is converted to epichlorohydrin.^[1] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)^[1] 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),^[2] reductive coupling to give diallyl, oxidative addition to palladium to give allylpalladium chloride dimer, (C₃H₅)₂Pd₂Cl₂, and dehydrohalogenation to cyclopropene.

Safety

Allyl chloride is highly toxic and flammable.

References

1. ^ ^{a b c} 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.
2. ^ J. V. Supniewski and P. L. Salzberg (1941), "Allyl Cyanide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0046 ; Coll. Vol. 1: 46 

External links

• International Chemical Safety Card 0010
• NIOSH Pocket Guide to Chemical Hazards 0018
• IARC Monograph *Allyl chloride.