tert-Butylamine

Template:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox Lethal amounts (set)Template:Chembox SDSTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer

tert-Butylamine

Template:Chembox image sbs cell
Template:Longitem	Template:Unbulleted list
Template:Longitem	605267
ChEBI	Template:Unbulleted list
ChemSpider	Template:Unbulleted list
DrugBank	Template:Unbulleted list
EC Number	Template:Unbulleted list
Template:Longitem	1867
KEGG	Template:Unbulleted list
MeSH	tert-butylamine
Template:Longitem	Template:Unbulleted list
RTECS number	Template:Unbulleted list
UN number	3286
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Odor	fishy, ammoniacal
Density	0.696 g/mL
Melting point	Template:Chembox CalcTemperatures
Boiling point	Template:Chembox CalcTemperatures
log P	0.802
Vapor pressure	39.29 kPa (at 20 °C)
Template:Longitem	1.377
Template:Longitem	191.71 J K−1 mol−1
Template:Longitem	233.63 J K−1 mol−1
Template:Longitem	−151.1–−150.1 kJ mol−1
Template:Longitem	−2.9959–−2.9951 MJ mol−1
NFPA 704 (fire diamond)	Template:NFPA 704 diamond
Flash point	Template:Chembox CalcTemperatures
Template:Longitem	Template:Chembox CalcTemperatures
Explosive limits	1.7–9.8%
Template:Longitem	Template:Unbulleted list
Template:Longitem	2-Methyl-2-nitrosopropane

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.

See also

• Borane tert-butylamine complex