Allyl iodide

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl 2-pyrrolidones,[1] sorbic acid esters,[1] 5,5-disubstituted barbituric acids,[2] and organometallic catalysts.[3] Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite,[4] Finkelstein reaction on allyl halides,[5] or by the action of elemental phosphorus and iodine on glycerol.[6][7] Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at −5 °C (23 °F) before decomposition into free iodine becomes apparent.[8]

Allyl iodide

Names
Preferred IUPAC name 3-Iodoprop-1-ene
Other names Allyl iodide 3-Iodopropene 3-Iodopropylene 3-Iodo-1-propene Iodoallylene 2-Propenyl iodide
Identifiers
CAS Number	556-56-9
3D model (JSmol)	Interactive image Interactive image
ChemSpider	21171407
ECHA InfoCard	100.008.302
EC Number	209-130-4
PubChem CID	11166
UNII	46830QOA4D
UN number	1723
CompTox Dashboard (EPA)	DTXSID5060302
InChI InChI=1S/C3H5I/c1-2-3-4/h2H,1,3H2 Key: BHELZAPQIKSEDF-UHFFFAOYSA-N InChI=1/C3H5I/c1-2-3-4/h2H,1,3H2
SMILES ICC=C C=CCI
Properties
Chemical formula	C3H5I
Molar mass	167.977 g·mol^−1
Appearance	Pale yellow liquid
Density	1.837 g/cm^3
Melting point	−99 °C (−146 °F; 174 K)
Boiling point	101 to 103 °C (214 to 217 °F; 374 to 376 K)
Hazards
Safety data sheet	MSDS at Sigma Aldrich
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H314
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
Flash point	18 °C (64 °F; 291 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Allyl
• Allyl alcohol
• Allyl bromide
• Allyl chloride

References

1. Bertleff, Werner (2000). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry. p. 20. doi:10.1002/14356007.a05_217. ISBN 978-3527306732. Missing or empty |title= (help)
2. Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry. p. 11. doi:10.1002/14356007.a13_533. ISBN 978-3527306732. Missing or empty |title= (help)
3. Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. p. 10. doi:10.1002/14356007.a18_215. ISBN 978-3527306732. Missing or empty |title= (help)
4. Patnaik, Pradyot (2007). A Comprehensive Guide to the Hazardous Properties of Chemical Substances 3rd Ed. New Jersey: John Wiley & Sons. pp. 141–142. ISBN 9780471714583.
5. Adams, Rodger (1944). Organic Reactions, Volume II. New York: John Wiley & Sons, Inc. p. 22.
6. Schorlemmer, C. (1874). A manual of the chemistry of the carbon compounds. London: Macmillan and Co. p. 262.
7. Datta, Rasek Lal (March 1914). "The Preparation of Allyl Iodide". Journal of the American Chemical Society. 36 (5): 1005–1007. doi:10.1021/ja02182a023. Retrieved 15 December 2013.
8. Armarego, Wilfred; Chai. Christina (2012). Purification of Laboratory Chemicals. Kidlington: Elsevier. p. 114. ISBN 9780123821614.