1138. Benzylideneaniline

Nomenclature

CAS number: 538-51-2; 1750-36-3 ((E)-form) ; 33993-35-0 ((Z)-form)
N-(Phenylmethylene)benzenamine; benzalaniline; benzaldehyde N-phenylimine; N-phenylbenzaldimine.
C13H11N; mol wt 181.23.
C 86.16%, H 6.12%, N 7.73%.

Description and references

Prepn from aniline and benzaldehyde: O. Hinsberg, Ber. 20, 1585 (1887); A. Hantzsch, O. Schwab, ibid. 34, (1901); L. A. Bigelow, H. Eatough, Org. Synth. coll. vol. I (2nd ed., 1941) p 80. Molecular structure: M. Traetteberg et al., J. Mol. Struct. 48, 395 (1978). Absorption spectrum: Baly et al., J. Chem. Soc. 97, 590 (1910).

Chemical structure

Properties

Crystals from 85% ethanol, mp 52°. Irritant. d450 1.045. bp760 300°. Sol in alcohol, chloroform, acetic anhydride, carbon disulfide.

Use

Reagent in organic synthesis.