Benzyl iodide
{{distinguish|iodotoluene}}
{{Chembox
| ImageFile = Benzyl iodide.svg
| ImageSize = 200px
| ImageAlt =
| PIN = (Iodomethyl)benzene
| OtherNames = Fraissite, iodotoluol, α-iodotoluene, phenylmethyliodide
| Section1 = {{Chembox Identifiers
| CASNo = 620-05-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 859JV557EV
| PubChem = 12098
| ChemSpiderID = 11601
| EINECS =
| SMILES = C1=CC=C(C=C1)CI
| StdInChI= 1S/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
| StdInChIKey= XJTQJERLRPWUGL-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=7|H=7|I=1
| Appearance = Low-melting crystals or colorless liquid
| Density =
| Solubility = Insoluble
| MeltingPt = 24.5 °C
| BoilingPtC = 218
| VaporPressure =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS07}} {{GHS09}}
| GHSSignalWord = WARNING
| HPhrases =
| PPhrases =
| FlashPtC = 86
| AutoignitionPt =
}}
}}
Benzyl iodide is an organic compound with the chemical formula {{chem|C|7|H|7|I}}.{{cite web|title=BENZYL IODIDE|url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB2305798.htm|publisher=chemicalbook.com|access-date=8 June 2017}}{{cite web|title=Benzyl iodide|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C620053&Mask=8|website=NIST|publisher=webbook.nist.gov|access-date=8 June 2017}} The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes.
Synthesis
Benzyl iodide can be obtained via the Finkelstein reaction from benzyl chloride and sodium iodide in acetone.
Properties
Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C.CRC Handbook of Chemistry and Physics, 90. Edition, CRC Press, Boca Raton, Florida, 2009, {{ISBN|978-1-4200-9084-0}}, Section 3, Physical Constants of Organic Compounds, p. 3-306. As a liquid, the compound has the high refractive index of 1.6334. Benzyl iodide is also a powerful lachrymator.{{cite book|last1=Bauta|first1=William E.|title=Encyclopedia of Reagents for Organic Synthesis|publisher=onlinelibrary.wiley.com|doi=10.1002/047084289X.rb060|year=2001|isbn=978-0471936237|chapter=Benzyl Iodide}}{{cite book|last1=Fieser|first1=Louis F.|last2=Fieser|first2=Mary|title=Organische Chemie|date=1982|publisher=Wiley |isbn=978-3-527-25075-2|language=de}}
See also
References
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{{Chemical agents}}