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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

Daily Sensitivity Test

What is the Correct Way to Check Repeatability in Balances?

Weighing the right way

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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