Allyl iodide

{{chembox

| ImageFile = Allyl iodide.png

| PIN = 3-Iodoprop-1-ene

| OtherNames = Allyl iodide
3-Iodopropene
3-Iodopropylene
3-Iodo-1-propene
Iodoallylene
2-Propenyl iodide

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21171407

| SMILES1 = C=CCI

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C3H5I/c1-2-3-4/h2H,1,3H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BHELZAPQIKSEDF-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 556-56-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 46830QOA4D

| EINECS = 209-130-4

| UNNumber = 1723

| PubChem = 11166

| SMILES = ICC=C

| InChI = 1/C3H5I/c1-2-3-4/h2H,1,3H2

}}

|Section2={{Chembox Properties

| C=3|H=5|I=1

| Appearance = Pale yellow liquid

| Density = 1.837 g/cm³

| MeltingPtC = −99

| BoilingPtC = 101 to 103

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=238325&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F238325%3Flang%3Den MSDS at Sigma Aldrich]

| GHSPictograms = {{GHS02}}{{GHS05}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225|314}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}}

| MainHazards =

| FlashPtC = 18

}}

}}

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones,{{Cite encyclopedia|last=Bertleff|first=Werner|chapter=Carbonylation|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|pages=9,14–15|doi=10.1002/14356007.a05_217|isbn=978-3527306732|quote=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.}}{{failed verification|reason=No content specific to the iodide, just generic allyl halides (typically chloride)|date=October 2023}} sorbic acid esters, 5,5-disubstituted barbituric acids,{{Cite encyclopedia|last=Wollweber|first=Hartmund|chapter=Hypnotics|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|page=521|doi=10.1002/14356007.a13_533|isbn=978-3527306732|quote=Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides.}}{{failed verification|reason=No content specific to the iodide, just generic allyl halides (typically chloride)|date=October 2023}} and organometallic catalysts.{{Cite encyclopedia|last=Behr|first=Arno|chapter=Organometallic Compounds and Homogeneous Catalysis|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|page=10|doi=10.1002/14356007.a18_215|isbn=978-3527306732|quote=Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds.}}{{failed verification|reason=No content specific to the iodide, just generic allyl halides (typically chloride)|date=October 2023}} Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite,{{cite book|last=Patnaik|first=Pradyot|title=A Comprehensive Guide to the Hazardous Properties of Chemical Substances 3rd Ed|year=2007|publisher=John Wiley & Sons|location=New Jersey|isbn=9780471714583|pages=141–142|url=https://books.google.com/books?id=-CRRJBVv5d0C&q=allyl+iodide&pg=PA141}} Finkelstein reaction on allyl halides,{{cite book|last=Adams|first=Rodger|title=Organic Reactions, Volume II|year=1944|publisher=John Wiley & Sons, Inc.|location=New York|pages=22|url=https://www.scribd.com/doc/101455067/Organic-Reactions-v2}} or by the action of elemental phosphorus and iodine on glycerol.{{cite book|last=Schorlemmer, C.|title=A manual of the chemistry of the carbon compounds|year=1874|publisher=Macmillan and Co.|location=London|page=262|url=https://books.google.com/books?id=VHEDAAAAQAAJ&q=262&pg=PR3}}{{cite journal|last=Datta|first=Rasek Lal|title=The Preparation of Allyl Iodide|journal=Journal of the American Chemical Society|date=March 1914|volume=36|issue=5|pages=1005–1007|doi=10.1021/ja02182a023|url=https://books.google.com/books?id=BrI7AQAAMAAJ&pg=PA1005|access-date=15 December 2013}} Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at {{convert|-5|C|F}} before decomposition into free iodine becomes apparent.{{cite book|author1=Armarego, Wilfred |author2=Chai. Christina|title=Purification of Laboratory Chemicals|year=2012|publisher=Elsevier|location=Kidlington|isbn=9780123821614|page=114|url=https://books.google.com/books?id=4ViVUQi7Z60C}}