Tert-Butylamine

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tert-Butylamine
Skeletal formula of tert-butylamine Tert-Butylamin Strukturformel.svg
Skeletal formula of tert-butylamine
Tert-Butylamine molecule ball.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-888-1
1867
MeSH tert-butylamine
PubChem CID
RTECS number
  • EO3330000
UNII
UN number 3286
  • InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3 Yes check.svgY
    Key: YBRBMKDOPFTVDT-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)N
Properties
C4H11N
Molar mass 73.139 g·mol−1
AppearanceColorless 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
Std molar
entropy (S⦵298)
233.63 J K−1 mol−1
−151.1–−150.1 kJ mol−1
−2.9959–−2.9951 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Danger
H225, H302, H314, H331
P210, P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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)
380 °C (716 °F; 653 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
464 mg kg−1(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 [77 °F], 100 kPa).

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.

Contents

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.

See also

Related Research Articles

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<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.

tert-Butyl chloride is the organochloride with the formula (CH3)3CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.

<i>sec</i>-Butylamine Chemical compound

sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH3CH2CH(NH2)CH3. It is a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine, and isobutylamine. sec-Butylamine is chiral and therefore can exist in either of two enantiomeric forms.

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tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.

<i>tert</i>-Butyl hydroperoxide Chemical compound

tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable.

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Aminomethyl propanol (AMP) is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.

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<i>tert</i>-Butyl hypochlorite Chemical compound

tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).

<i>tert</i>-Butoxybis(dimethylamino)methane Chemical compound

tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.

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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