View source for Allyl chloride

{{Chembox new|
 ImageFile=Allyl_chloride.png|
 IUPACName=3-Chloropropene<br />Allyl chloride|
 Formula=C<sub>3</sub>H<sub>5</sub>Cl|
 MolarMass=76.53 g/mol|
 CASNo=107-05-1|
 Density=0.94 g/mL|
 MeltingPt=&minus;135 °C|
 BoilingPt=45 °C|
 Solubility=0.36 g/100 mL (20 °C)|
  Solvent=Water|
 SMILES=C=CCCl|
 Section1={{Chembox Hazards|
  EUClass=Flammable ('''F''')<br />Harmful ('''Xn''')<br />{{Carc3}}<br />{{Muta3}}<br />Dangerous for<br />the environment ('''N''')|
  EUIndex=602-029-00-X|
  NFPA-H=3|
  NFPA-F=3|
  NFPA-R=1|
  RPhrases={{R11}}, {{R20/21/22}},<br />{{R36/37/38}}, {{R40}},<br />{{R40}}, {{R48/20}}, {{R68}}, |
  SPhrases={{S2}}, {{S16}}, {{S25}}, {{S26}},<br />{{S36/37}}, {{S46}}, {{S61}}|
  FlashPt=&minus;32 °C|
  Autoignition=390 °C|
  ExploLimits=2.9&ndash;11.2%}}}}

{{SI}}


==Overview==
'''Allyl chloride''' is a colorless [[liquid]] with the [[chemical formula]] [[Carbon|C]][[Hydrogen|H]]<sub>2</sub>=[[Carbon|C]][[Hydrogen|H]][[Carbon|C]][[Hydrogen|H]]<sub>2</sub>[[Chlorine|Cl]].  It features an alkene group next to, or "allylic to", an alkyl halide group,  It is [[soluble|insoluble]] in [[water]] but soluble in common organic solvents.  It is a common as an [[alkylating agent]] relevant to the manufacture of [[pharmaceutical]]s and [[pesticide]]s. It is also a component in [[thermoset]]ting [[resin]]s.

Allyl chloride is a common building block in [[organic synthesis]]. Illustrative important reactions include cyanation to allyl cyanide (CH<sub>2</sub>=CHCH<sub>2</sub>CN), reductive coupling to give diallyl,CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>2</sub>CH=CH<sub>2</sub>), complexation to [[palladium]] to give allyl palladium dimer, (C<sub>3</sub>H<sub>5</sub>)<sub>2</sub>Pd<sub>2</sub>Cl<sub>2</sub>, 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]].

== External links ==
*{{ICSC|0010|00}}
*{{PGCH|0018}}
*[[IARC]] Monograph *[http://www-cie.iarc.fr/htdocs/monographs/vol71/055-allylchl.html Allyl chloride.]


[[Category:Alkenes]]
[[Category:Organochlorides]]
[[Category:IARC Group 3 carcinogens]]

[[ja:アリル化合物]]
[[vi:Allyl clorua]]

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