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
Boiling point	45 °C
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 (what is this?)  (verify) 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 features an alkene group next to, or "allylic to", a chloro methyl group.

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]

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. Commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)^[1] and allylsilane.

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.