6026. α-Methylbenzylamine

Nomenclature

CAS number: 98-84-0
α-Methylbenzenemethanamine; α-phenylethylamine; 1-phenylethylamine; α-aminoethylbenzene.
C8H11N; mol wt 121.18.
C 79.29%, H 9.15%, N 11.56%.

Description and references

Prepn from acetophenone and ammonium formate: A. W. Ingersoll et al., J. Am. Chem. Soc. 58, 1808 (1936); by reduction of acetophenone in liquid ammonia: J. C. Robinson, H. R. Snyder, Org. Synth. coll. vol. III, 717 (1955). Stereospecific synthesis of R-(+)-form: H. Takahashi et al., Chem. Pharm. Bull. 29, 3387 (1981). Resolution of (dl)-methylbenzylamine: W. Theikecker, H.-G. Winkler, Ber. 87, 690 (1954). Use of (R)-(+)-methylbenzylamine as resolving agent: E. J. Corey, J. Mann, J. Am. Chem. Soc. 95, 6832 (1973). Use as chiral intermediate in synthesis of α-methyl-α-amino nitriles: K. Weinges et al., Ber. 110, 2098 (1977); of β-amino acids: M. Furukawa et al., Chem. Pharm. Bull. 26, 260 (1978). Toxicity: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).

Chemical structure

Derivative

dl-Form.

Properties

Liquid. Aromatic odor. Absorbs CO2 from air. d415 0.9395. bp18 80-81°. Strong base. Soly in water at 20° about 4.2%. Misc with alcohol, ether. LD50 orally in rats: 0.94 g/kg (Smyth).

Derivative

(+)-Form.

Properties

Liquid, bp 184-186°. d422 0.950. [α]D22 +40.3° (neat).

Derivative

()-Form.

Properties

Liquid, bp12 73°. d422 0.950. [α]D22 40.3° (neat).

Use

As resolving agent; chiral intermediate.