Benzyl iodide is an organic compound with the chemical formula . The compound consists of a

benzene ring Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

with an attached iodidemethyl group. The substance is an

alkyl halide The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely us ...

and is a constitutional isomer of the iodotoluenes.

Synthesis

Benzyl iodide can be obtained via the

Finkelstein reaction The Finkelstein reaction named after the German chemist Hans Finkelstein, is an SN2 reaction (Substitution Nucleophilic Bimolecular reaction) that involves the exchange of one halogen atom for another. It is an equilibrium reaction, but the rea ...

from

benzyl chloride Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared indu ...

and

sodium iodide Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine. Under standard conditions, it is a white, water-soluble solid comprising a 1:1 mix of sodium cations (Na+) and iodide anions (I ...

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

Synthesis of Benzyl Iodide from Benzyl Chloride

Properties

Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C.''

CRC Handbook of Chemistry and Physics The ''CRC Handbook of Chemistry and Physics'' is a comprehensive one-volume reference resource for science research. First published in 1914, it is currently () in its 103rd edition, published in 2022. It is sometimes nicknamed the "Rubber Bible ...

'', 90. Edition, CRC Press, Boca Raton, Florida, 2009, , Section 3, ''Physical Constants of Organic Compounds'', p. 3-306. As a liquid, the compound has the high

refractive index In optics, the refractive index (or refraction index) of an optical medium is a dimensionless number that gives the indication of the light bending ability of that medium. The refractive index determines how much the path of light is bent, o ...

of 1.6334. Benzyl iodide is also a powerful

lachrymator Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...

References

{{Chemical agents Organoiodides Benzyl compounds Lachrymatory agents

Synthesis

Properties

See also

References