Tert-Butylamine

tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.

Preparation
tert-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts:
 * NH3 +  CH2=C(CH3)2  →   H2NC(CH3)3

The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste.


 * (CH3)2C=CH2 +  HCN  +  H2O   →   (CH3)3CNHCHO
 * (CH3)3CNHCHO +  H2O   →   (CH3)3CNH2  +  HCO2H

In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.

Uses
tert-Butylamine is used as an intermediate in the preparation of the sulfenamides such as N-tert-butyl-2-benzothiazylsulfenamide and N-tert-butyl-2-benzothiazylsulfenimide. As rubber accelerators, these compounds modify the rate of vulcanization of rubber. A variety of pesticides are derived from this amine, including terbacil, terbutryn, and terbumeton.

In pharmacology under the name erbumine, tert-butylamine has been used as a counterion in drug substances such as perindopril erbumine.