tert-Butylamine

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
75-64-9 YesY
3D model (Jmol) Interactive image
605267
ChEBI CHEBI:44639 YesY
ChEMBL ChEMBL13782 YesY
ChemSpider 6145 YesY
ECHA InfoCard 100.000.808
EC Number 200-888-1
1867
MeSH tert-butylamine
PubChem 6385
RTECS number EO3330000
UN number 3286
Properties
C4H11N
Molar mass 73.14 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
−151.1–−150.1 kJ mol−1
−2.9959–−2.9951 MJ mol−1
Hazards
Safety data sheet rose-hulman.edu
GHS pictograms
GHS signal word DANGER
H225, H302, H314, H331
P210, P261, P280, P305+351+338, P310
F C
R-phrases R11, R20/22, R35
S-phrases S16, S26, S36/37/39, S45
NFPA 704
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., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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

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.

Preparation

tert-Butylamine is produced commercially by the Ritter reaction of isobutene with hydrogen cyanide under acidic conditions to give the formamide:[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 or 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. ↑ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_001
  2. ↑ Kenneth N. Campbell, Armiger H. Sommers, and Barbara K. Campbell (1955). "tert'-Butylamine". Org. Synth.; Coll. Vol., 3, p. 148
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