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Allyl chloride

IUPAC name

3-Chloropropene
Allyl chloride

Molecular formula

C₃H₅Cl

Molar mass

76.53 g/mol

CAS number

107-05-1

Density

0.94 g/mL

Solubility

0.36 g/100 mL (20 °C)

Melting point

−135 °C

Boiling point

45 °C

SMILES

C=CCCl

Hazards

EU classification

Flammable (F)
Harmful (Xn)
Carc. Cat. 3
Muta. Cat. 3
Dangerous for
the environment (N)

EU Index

602-029-00-X

NFPA 704

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

Autoignition
temperature

390 °C

Explosive limits

2.9–11.2%

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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 a common alkylating agent relevant to the manufacture of pharmaceuticals and pesticides. It is also a component in some thermosetting resins. It features an alkene group next to, or "allylic to", an chloride group.

Additional recommended knowledge

Weighing the right way

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Don't let static charges disrupt your weighing accuracy

Allyl chloride is a common building block in organic synthesis. Illustrative reactions include its cyanation to allyl cyanide (CH₂=CHCH₂CN),^[1] reductive coupling to give diallyl,CH₂=CHCH₂CH₂CH=CH₂), oxidative addition to palladium to give allylpalladium chloride dimer, (C₃H₅)₂Pd₂Cl₂, and dehydrohalogenation to cyclopropene.

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

CH₃CH=CH₂ + Cl₂ → ClCH₂CH=CH₂ + HCl

Safety

Allyl chloride is toxic and flammable.

References

^ J. V. Supniewski and P. L. Salzberg (1941). "Allyl Cyanide". Org. Synth.; Coll. Vol. 1: 46.

Category: IARC Group 3 carcinogens

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Allyl_chloride". A list of authors is available in Wikipedia.

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