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Tert-Butylamine

| NFPA-H = 3 | NFPA-R = 0 | NFPA-F = 4

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.

References

References

  1. (2000). "Amines, Aliphatic".
  2. Kenneth N. Campbell, Armiger H. Sommers, Barbara K. Campbell. (1947). "''tert''-Butylamine". Organic Syntheses.
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alkylamines tert-butyl-compounds
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