Allyl iodide
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| 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 | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.008.302 |
| EC Number |
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PubChem CID
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| UN number | 1723 |
CompTox Dashboard (EPA)
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| Properties | |
| C3H5I | |
| Molar mass | 167.977 g·mol−1 |
| Appearance | Pale yellow liquid |
| Density | 1.837 g/cm3 |
| Melting point | −99 °C (−146 °F; 174 K) |
| Boiling point | 101 to 103 °C (214 to 217 °F; 374 to 376 K) |
| Hazards | |
| Flash point | 18 °C (64 °F; 291 K) |
| Safety data sheet (SDS) | MSDS at Sigma Aldrich |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
See also
References
- ^ a b Bertleff, Werner (2000). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg. 20. doi:10.1002/14356007.a05_217. Retrieved 17 December 2013.
{{cite journal}}:|page=has extra text (help) - ^ Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry: pg. 11. doi:10.1002/14356007.a13_533.
{{cite journal}}:|page=has extra text (help) - ^ Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry: pg. 10. doi:10.1002/14356007.a18_215.
{{cite journal}}:|page=has extra text (help) - ^ 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.
- ^ Adams, Rodger (1944). Organic Reactions, Volume II. Newyork: John Wiley & Sons, Inc. p. 22.
- ^ Schorlemmer, C. (1874). A manual of the chemistry of the carbon compounds. London: Macmillan and Co. p. 262.
- ^ Datta, Rasek Lal (March 1914). "The Preparation of Allyl Iodide". Journal of the American Chemical Society. 36: 1005–1007. doi:10.1021/ja02182a023. Retrieved 15 December 2013.
- ^ Armarego, Wilfred; Chai. Christina (2012). Purification of Laboratory Chemicals. Kidlington: Elsevier. p. 114. ISBN 9780123821614.
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