Allyl iodide

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/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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

Allyl iodide (3-iodopropene) is an

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]

References

^
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.

ISBN 978-3527306732
. Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides.

ISBN 978-3527306732
. Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds.

ISBN 9780471714583
.

^ Adams, Rodger (1944). Organic Reactions, Volume II. New York: John Wiley & Sons, Inc. p. 22.

^ Schorlemmer, C. (1874). A manual of the chemistry of the carbon compounds. London: Macmillan and Co. p. 262.

doi:10.1021/ja02182a023
. Retrieved 15 December 2013.

ISBN 9780123821614
.

organic halide is a stub. You can help Wikipedia by expanding it.
v
t
e

[Carbonylation-1] 
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] ISBN 978-3527306732
. Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides.

[3] ISBN 978-3527306732
. Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds.

[4] 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] :10.1021/ja02182a023
. Retrieved 15 December 2013.

[8] ISBN 9780123821614
.

[4]

[5]

[6]

[7]

[8]

See also

References