View source for Allyl chloride

{{chembox
| Watchedfields = changed
| verifiedrevid = 322317383
| ImageFile1=Allyl_chloride.png
| ImageSize1=200px
| ImageFileL2=Allyl-chloride-3D-balls.png
| ImageSize1=120px
| ImageFileR2=Allyl-chloride-3D-vdW.png
| ImageSize1=120px
| IUPACName=1-Chloroprop-2-ene
| Section2 = {{Chembox Identifiers
| InChI = 1/C3H5Cl/c1-2-3-4/h2H,1,3H2
| InChIKey = OSDWBNJEKMUWAV-UHFFFAOYAQ
| CASNo_Ref = {{cascite}}
| CASNo=107-05-1
| SMILES=C=CCCl
  }}
| Section2 = {{Chembox Properties
| C=3|H=5|Cl=1
| Density=0.94 g/mL
| MeltingPtC=-135 
| BoilingPtC=45
| Solubility=0.36 g/100 mL (20 °C)
| Solvent=Water
| ChemSpiderID = 7562
}}
|Section4={{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}} {{R36/37/38}} {{R40}} {{R40}} {{R48/20}} {{R68}} {{R50}}
|  SPhrases={{S2}} {{S16}} {{S25}} {{S26}} {{S36/37}} {{S46}} {{S61}}
|  FlashPt=&minus;32 °C
|  Autoignition=390 °C
|  ExploLimits=2.9&ndash;11.2%
  }}
}}

'''Allyl chloride''' is the [[organic compound]] with the [[chemical formula|formula]] [[Carbon|C]][[Hydrogen|H]]<sub>2</sub>=CHCH<sub>2</sub>[[Chlorine|Cl]]. This colorless [[liquid]] is [[soluble|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]].

==Production==
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:
:CH<sub>3</sub>CH=CH<sub>2</sub>  +  Cl<sub>2</sub>   →  ClCH<sub>2</sub>CH=CH<sub>2</sub>  +  [[Hydrogen chloride|HCl]]
An estimated 800M kg are produced in this way annually.<ref name=Ullmann>Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June, 2000.</ref>

==Reactions and uses==
The great majority of allyl chloride is converted to [[epichlorohydrin]].<ref name=Ullmann/>  Other commercially significant derivatives include [[allyl alcohol]], [[allylamine]], [[allyl isothiocyanate]] (synthetic mustard oil)<ref name=Ullmann>F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.</ref> and [[allylsilane]].

In the laboratory, allyl chloride is a common [[alkylating agent]], useful in the manufacture of [[pharmaceutical]]s and [[pesticide]]s.<!--for example?-->  Illustrative of its reactivity include its [[cyanation]] to [[allyl cyanide]] (CH<sub>2</sub>=CHCH<sub>2</sub>CN),<ref>{{OrgSynth | author = J. V. Supniewski and P. L. Salzberg | title = Allyl Cyanide | collvol = 1 | collvolpages = 46 | year = 1941 | prep = CV1P0046}}</ref> reductive coupling to give [[diallyl]], [[oxidative addition]] to [[palladium]] to give [[allylpalladium chloride dimer]], (C<sub>3</sub>H<sub>5</sub>)<sub>2</sub>Pd<sub>2</sub>Cl<sub>2</sub>, and dehydrohalogenation to [[cyclopropene]].  

==Safety==
Allyl chloride is highly [[toxic]] and [[flammable]].

==Mapping of industrial releases in the United States==
One tool that maps the most recent release information for allyl chloride [http://toxmap.nlm.nih.gov/toxmap/main/mapIt.do?chemicalName=allyl+chloride] to particular locations in the United States<ref>{{cite web|url=http://toxmap.nlm.nih.gov/toxmap/main/mapIt.do?chemicalName=allyl+chloride|title=TRI Releases Map |publisher=Toxmap.nlm.nih.gov |accessdate=2010-03-23}}</ref> and also provides additional information about such releases is [[TOXMAP]]. TOXMAP is a Geographic Information System (GIS) from the Division of Specialized Information Services of the [[United States National Library of Medicine]] (NLM) that uses maps of the United States to help users visually explore data from the [[United States Environmental Protection Agency]]'s (EPA) [[Toxics Release Inventory]] and [[Superfund Basic Research Program]]s. TOXMAP is a resource funded by the US Federal Government. TOXMAP's chemical and environmental health information is taken from NLM's Toxicology Data Network (TOXNET)<ref>[http://toxnet.nlm.nih.gov TOXNET - Databases on toxicology, hazardous chemicals, environmental health, and toxic releases]</ref> and [[PubMed]], and from other authoritative sources.

==References==
<references/>

== 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]]


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