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tert-Butylamine

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tert-Butylamine
Skeletal formula of 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
CAS Number
3D model (JSmol)
Beilstein Reference 605267
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.808 Edit this at Wikidata
EC Number
  • 200-888-1
Gmelin Reference 1867
MeSH tert-butylamine
PubChem CID
RTECS number
  • EO3330000
UNII
UN number 3286
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3Key: YBRBMKDOPFTVDT-UHFFFAOYSA-N
SMILES
  • CC(C)(C)N
Properties
Chemical formula C4H11N
Molar mass 73.139 g·mol
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
Solubility in water Miscible
log P 0.802
Vapor pressure 39.29 kPa (at 20 °C)
Refractive index (nD) 1.377
Thermochemistry
Heat capacity (C) 191.71 J K mol
Std molar
entropy (S298) 		233.63 J K mol
Std enthalpy of
formation (ΔfH298) 		−151.1–−150.1 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−2.9959–−2.9951 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Signal word Danger
Hazard statements H225, H302, H314, H331
Precautionary statements P210, P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3 4 0
Flash point −38 °C (−36 °F; 235 K)
Autoignition
temperature 		380 °C (716 °F; 653 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose) 464 mg kg (oral, rat)
Safety data sheet (SDS) rose-hulman.edu
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 , 100 kPa). Infobox references
Chemical compound

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

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. ISBN 3527306730.
  2. Kenneth N. Campbell, Armiger H. Sommers, Barbara K. Campbell (1947). "tert'-Butylamine". Organic Syntheses. 47: 12. doi:10.15227/orgsyn.027.0012.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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