Allyl chloride | |
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1-Chloroprop-2-ene |
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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% |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
Contents |
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:
An estimated 800M kg are produced in this way annually.[1]
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.
Allyl chloride is highly toxic and flammable.