Misplaced Pages

Allyl iodide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.302 Edit this at Wikidata
EC Number
  • 209-130-4
PubChem CID
UNII
UN number 1723
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5I/c1-2-3-4/h2H,1,3H2Key: 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
Appearance Pale yellow liquid
Density 1.837 g/cm
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:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H225, H314
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones, sorbic acid esters, 5,5-disubstituted barbituric acids, and organometallic catalysts. Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite, Finkelstein reaction on allyl halides, or by the action of elemental phosphorus and iodine on glycerol. 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.

See also

References

  1. ^ 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.


Stub icon

This article about an organic halide is a stub. You can help Misplaced Pages by expanding it.

Categories: