10235. Benzophenone Imine

Nomenclature

CAS number: 1013-88-3
α-Phenylbenzenemethanimine; diphenyl ketimine; 1,1-diphenylmethylenimine.
C13H11N; mol wt 181.23.
C 86.16%, H 6.12%, N 7.73%.

Description and references

Reagent for protection of primary amines. Prepn of salt forms: A. Hantzsch, F. Kraft, Ber. 24, 3511 (1891). Prepn by addn of phenylmagnesium bromide to benzonitrile, followed by hydrolysis with CH3OH: P. L. Pickard, T. L. Tolbert, J. Org. Chem. 26, 4886 (1961) DOI; eidem, Org. Synth. coll. vol. V, 520 (1973); by reaction of benzophenone with NH3: G. Verardo et al., Synth. Commun. 18, 1501 (1988) DOI. Electrochemical properties: S. Zhan, M. D. Hawley, J. Electroanal. Chem. 319, 275 (1991) DOI. Synthetic applications: M. J. O'Donnell, Aldrichim. Acta 34, 3 (2001); Y. Liu et al., J. Heterocycl. Chem. 40, 713 (2003). Review: A. Crespo, Synlett 2006, 2345-2346 DOI.

Chemical structure

Properties

Liquid, bp3.5 127-128°. bp8 151-152°. nD20 1.6180-1.6191. d20 1.0849. Light sensitive. Store under Nitrogen.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5319-67-5
C13H11N.HCl; mol wt 217.69.
C 71.73%, H 5.56%, N 6.43%, Cl 16.29%.

Properties

mp 139°. Sol in cold water; slightly sol in chloroform. Insol in ether, benzene.

Use

Protecting group for primary amines in peptide chemistry; ammonia surrogate in catalyzed coupling reactions.