Benzyl iodide

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Benzyl iodide
Benzyl iodide.svg
Names
Preferred IUPAC name
(Iodomethyl)benzene
Other names
Fraissite, iodotoluol, α-iodotoluene, phenylmethyliodide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.659 Edit this at Wikidata
UNII
  • InChI=1S/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
    Key: XJTQJERLRPWUGL-UHFFFAOYSA-N
  • C1=CC=C(C=C1)CI
Properties
C7H7I
Molar mass 218.037 g·mol−1
Appearance Low-melting crystals or colorless liquid
Melting point 24.5 °C
Boiling point 218 °C (424 °F; 491 K)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation mark GHS09: Environmental hazard
Warning
Flash point 86 °C (187 °F; 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzyl iodide is an organic compound with the chemical formula C
7
H
7
I
.[1][2] 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[edit]

Benzyl iodide can be obtained via the Finkelstein reaction from benzyl chloride and sodium iodide in acetone.

Synthesis of benzyl iodide by Finkelstein reaction

Properties[edit]

Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C.[3] As a liquid, the compound has the high refractive index of 1.6334. Benzyl iodide is also a powerful lachrymator.[4][5]

See also[edit]

References[edit]

  1. ^ "BENZYL IODIDE". chemicalbook.com. Retrieved 8 June 2017.
  2. ^ "Benzyl iodide". NIST. webbook.nist.gov. Retrieved 8 June 2017.
  3. ^ 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.
  4. ^ Bauta, William E. (2001). "Benzyl Iodide". Encyclopedia of Reagents for Organic Synthesis. onlinelibrary.wiley.com. doi:10.1002/047084289X.rb060. ISBN 978-0471936237.
  5. ^ Fieser, Louis F.; Fieser, Mary (1982). Organische Chemie (in German). ISBN 978-3-527-25075-2.