tert-Butylamine

tert-Butylamine

Skeletal formula of tert-butylamine Ball and stick model of the tert-butylamine molecule
Names
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	75-64-9 Y
Beilstein Reference	605267
ChEBI	CHEBI:44639 Y
ChEMBL	ChEMBL13782 Y
ChemSpider	6145 Y
EC Number	200-888-1
Gmelin Reference	1867
Jmol 3D model	Interactive image
MeSH	tert-butylamine
PubChem	6385
RTECS number	EO3330000
UN number	3286
InChI InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3 Y Key: YBRBMKDOPFTVDT-UHFFFAOYSA-N Y
SMILES CC(C)(C)N
Properties
Chemical formula	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
Solubility in water	Miscible
log P	0.802
Vapor pressure	39.29 kPa (at 20 °C)
Refractive index (nD)	1.377
Thermochemistry
Specific heat capacity (C)	191.71 J K−1 mol−1
Std molar entropy (So298)	233.63 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−151.1–−150.1 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.9959–−2.9951 MJ mol−1
Vapor pressure	{{{value}}}
Related compounds
Related alkanamines	Ethylamine Ethylenediamine Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine n-Butylamine sec-Butylamine Putrescine
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:

(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 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

• Borane tert-butylamine complex