alpha-Methylbenzylamine

Title: a-Methylbenzylamine
CAS Registry Number: 98-84-0
CAS Name: a-Methylbenzenemethanamine
Additional Names: a-phenylethylamine; 1-phenylethylamine; a-aminoethylbenzene
Molecular Formula: C8H11N
Molecular Weight: 121.18
Percent Composition: C 79.29%, H 9.15%, N 11.56%
Literature 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 a-methyl-a-amino nitriles: K. Weinges et al., Ber. 110, 2098 (1977); of b-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).
Derivative Type: 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).
Boiling point: bp18 80-81°
Density: d415 0.9395
Toxicity data: LD50 orally in rats: 0.94 g/kg (Smyth)
Derivative Type: (+)-Form
Properties: Liquid, bp 184-186°. d422 0.950. [a]D22 +40.3° (neat).
Boiling point: bp 184-186°
Optical Rotation: [a]D22 +40.3° (neat)
Density: d422 0.950
Derivative Type: (-)-Form
Properties: Liquid, bp12 73°. d422 0.950. [a]D22 -40.3° (neat).
Boiling point: bp12 73°
Optical Rotation: [a]D22 -40.3° (neat)
Density: d422 0.950
Use: As resolving agent; chiral intermediate.
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