Allyl iodide

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.302 Edit this at Wikidata
EC Number
  • 209-130-4
UNII
UN number 1723
  • InChI=1S/C3H5I/c1-2-3-4/h2H,1,3H2 checkY
    Key: BHELZAPQIKSEDF-UHFFFAOYSA-N checkY
  • InChI=1/C3H5I/c1-2-3-4/h2H,1,3H2
  • ICC=C
  • C=CCI
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
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
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).

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones,[1][failed verification] sorbic acid esters,[1] 5,5-disubstituted barbituric acids,[2][failed verification] and organometallic catalysts.[3][failed verification] 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

  1. ^ a b Bertleff, Werner (2000). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry. pp. 9, 14–15. doi:10.1002/14356007.a05_217. ISBN 978-3527306732. When unsaturated amines are carbonylated in the presence of Co2(CO)8, N-alkyl pyrrolidinones are obtained. Carbonylation of allyl halides in the presence of primary amines and a rhodium compound affords the same products....If allyl derivatives are carbonylated in the presence of acetylene by means of Ni(CO)4 and water or methanol at 20 °C, the acetylene adds onto the allyl halide and 2-cis-5-dienoic acids or esters or sorbic acid esters are obtained.
  2. ^ Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry. p. 521. doi:10.1002/14356007.a13_533. ISBN 978-3527306732. Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides.
  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. Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds.
  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.


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