Allyl chloride

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Allyl chloride
IUPAC name 3-Chloropropene
Allyl chloride
Molecular formula C3H5Cl
Molar mass 76.53 g/mol
Density 0.94 g/mL
Solubility 0.36 g/100 mL (20 °C)
Melting point

−135 °C

Boiling point

45 °C

Hazards
EU classification {{{value}}}
R-phrases R11, R20/21/22,
R36/37/38, R40,
R40, R48/20, R68,
S-phrases (S2), S16, S25, S26,
S36/37, S46, S61
Flash point {{{value}}}
Explosive limits 2.9–11.2%
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

Allyl chloride is a colorless liquid with the chemical formula CH2=CHCH2Cl. It features an alkene group next to, or "allylic to", an alkyl halide group, It is insoluble in water but soluble in common organic solvents. It is a common as an alkylating agent relevant to the manufacture of pharmaceuticals and pesticides. It is also a component in thermosetting resins.

Allyl chloride is a common building block in organic synthesis. Illustrative important reactions include cyanation to allyl cyanide (CH2=CHCH2CN), reductive coupling to give diallyl,CH2=CHCH2CH2CH=CH2), complexation to palladium to give allyl palladium dimer, (C3H5)2Pd2Cl2, and dehydrohalogenation to cyclopropene.

Allyl chloride is prepared by the reaction of propylene with chlorine gas at 500 °C.

Safety

Allyl chloride is toxic and flammable.

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