DL-alpha-Methylbenzylamine

Chemical properties

liquid

The Uses of DL-alpha-Methylbenzylamine

Used for synthesis and as an emulsifying agent; used as a resolving agent and chiral intermediate.

The Uses of DL-alpha-Methylbenzylamine

α-Methylbenzylamine can be used as a reactant for the synthesis of dihydro-5H-dibenz[c,e]azepinium salts by reacting with racemic biphenol derivatives.

Definition

ChEBI: A phenylethylamine that is ethylamine substituted by a phenyl group at position 1.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4272, 1984 DOI: 10.1021/jo00196a031
Chemical and Pharmaceutical Bulletin, 36, p. 1529, 1988 DOI: 10.1248/cpb.36.1529
Tetrahedron Letters, 27, p. 3957, 1986 DOI: 10.1016/S0040-4039(00)84883-2

General Description

α-Methylbenzylamine is a nitrogen source that is widely used as a representative substrate to study the chemo-enzymatic kinetic resolution of primary amines.

Flammability and Explosibility

Non flammable

Purification Methods

Dissolve the amine in toluene, dry over NaOH and distil; fraction boiling at 187-188o/atm is collected. Store it under N2 to avoid forming the carbamate and urea. Similarly for the S-(-) enantiomer [2627-86-3]. [Ingersoll Org Synth Coll Vol II 503 1943, Robinson & Snyder Org Synth Coll Vol III 717 1955, Beilstein 12 IV 2424, 2425.]