Benzyl iodide

Not to be confused with iodotoluene.
Benzyl iodide
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
7H
7I.[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

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

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

References

  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). Wiley. ISBN 978-3-527-25075-2.