Allyl iodide

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Allyl iodide
Allyl iodide
Names
IUPAC name
3-Iodopropene
Other names
Allyl iodide; 3-Iodopropene; 3-Iodopropylene; 3-Iodo-1-propene; Iodoallylene; 2-Propenyl iodide
Identifiers
556-56-9 YesY
ChemSpider 21171407 YesY
EC number 209-130-4
Jmol-3D images Image
Image
PubChem 11166
UN number 1723
Properties
C3H5I
Molar mass 167.98 g·mol−1
Appearance Pale yellow liquid
Density 1.837 g/cm3
Melting point −99 °C (−146 °F; 174 K)
Boiling point 101 °C (214 °F; 374 K)
Hazards
MSDS MSDS at Sigma Aldrich
EU classification Toxic (T), Flammable (F)
Flash point 18 °C (64 °F; 291 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 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[edit]

References[edit]

  1. ^ a b Bertleff, Werner (2000). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg. 20. doi:10.1002/14356007.a05_217. Retrieved 17 December 2013. 
  2. ^ Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry: pg. 11. doi:10.1002/14356007.a13_533. 
  3. ^ Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry: pg. 10. doi:10.1002/14356007.a18_215. 
  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. Newyork: 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: 1005–1007. doi:10.1021/ja02182a023. Retrieved 15 December 2013. 
  8. ^ Armarego, Wilfred; and Chai. Christina (2012). Purification of Laboratory Chemicals. Kidlington: Elsevier. p. 114. ISBN 9780123821614.