tert-Butylamine

tert-Butylamine 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.

tert-Butylamine
Skeletal formula of tert-butylamine
Ball and stick model of the tert-butylamine molecule
Names
Preferred IUPAC name
2-Methylpropan-2-amine
Other names
  • 2-Aminoisobutane
  • 2-Amino-2-methylpropane
  • Dimethylethylamine
  • 2-Methyl-2-aminopropane
  • 2-Methyl-2-propylamine
  • Trimethylaminomethane
  • Erbumine (INN)
Identifiers
3D model (JSmol)
605267
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.808
EC Number
  • 200-888-1
1867
MeSH tert-butylamine
RTECS number
  • EO3330000
UNII
UN number 3286
Properties
C4H11N
Molar mass 73.139 g·mol−1
Appearance Colorless liquid
Odor fishy, ammoniacal
Density 0.696 g/mL
Melting point −67.50 °C; −89.50 °F; 205.65 K
Boiling point 43 to 47 °C; 109 to 116 °F; 316 to 320 K
Miscible
log P 0.802
Vapor pressure 39.29 kPa (at 20 °C)
1.377
Thermochemistry
191.71 J K−1 mol−1
233.63 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −151.1–−150.1 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −2.9959–−2.9951 MJ mol−1
Hazards
Safety data sheet rose-hulman.edu
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H302, H314, H331
P210, P261, P280, P305+351+338, P310
NFPA 704 (fire diamond)
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
3
0
Flash point −38 °C (−36 °F; 235 K)
380 °C (716 °F; 653 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
464 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds
 2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

(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.[2]

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.

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See also
  • Borane tert-butylamine complex

References
  1. Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
  2. Kenneth N. Campbell, Armiger H. Sommers, Barbara K. Campbell (1947). "tert'-Butylamine". 47: 12. doi:10.15227/orgsyn.027.0012. Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
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