Benzyl iodide

Benzyl iodide
Names
	Preferred IUPAC name (Iodomethyl)benzene
	Other names Fraissite, iodotoluol, α-iodotoluene, phenylmethyliodide
Identifiers
CAS Number	620-05-3;
3D model (JSmol)	Interactive image;
ChemSpider	11601;
ECHA InfoCard	100.009.659
PubChem CID	12098;
UNII	859JV557EV ;
CompTox Dashboard (EPA)	DTXSID6060715 ;
	InChI InChI=1S/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: XJTQJERLRPWUGL-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)CI;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
	GHS labelling:
Pictograms
Signal word	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). Infobox references

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.

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

Synthesis of benzyl iodide by Finkelstein reaction

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]

[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.

[1] [1]
"BENZYL IODIDE". chemicalbook.com. Retrieved 8 June 2017.

[2] [2]
"Benzyl iodide". NIST. webbook.nist.gov. Retrieved 8 June 2017.

[CRC_HANDBOOK-3] [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] [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] [5]
Fieser, Louis F.; Fieser, Mary (1982). Organische Chemie (in German). Wiley. ISBN 978-3-527-25075-2.

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[2]

[3]

[4]

[5]

Benzyl iodide

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Synthesis

Properties

See also

References