tert-Butylamine

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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
ChemSpider
ECHA InfoCard 100.000.808
EC Number 200-888-1
1867
MeSH tert-butylamine
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 The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H302, H314, H331
P210, P261, P280, P305+351+338, P310
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
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[edit]

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[edit]

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[edit]

References[edit]

  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