Tert-Butylamine

tert-Butylamine

Skeletal formula of tert-butylamine
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	75-64-9  Y
3D model (JSmol)	Interactive image
Beilstein Reference	605267
ChEBI	CHEBI:44639  Y
ChEMBL	ChEMBL13782  Y
ChemSpider	6145  Y
ECHA InfoCard	100.000.808
EC Number	200-888-1
Gmelin Reference	1867
MeSH	tert-butylamine
PubChem CID	6385
RTECS number	EO3330000
UNII	91Z53KF68U  Y
UN number	3286
CompTox Dashboard (EPA)	DTXSID5024681
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	73.139 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
Heat capacity (C)	191.71 J K−1 mol−1
Std molar entropy (S⦵298)	233.63 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−151.1–−150.1 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−2.9959–−2.9951 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H331
Precautionary statements	P210, P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	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−1(oral, rat)
Safety data sheet (SDS)	rose-hulman.edu
Related compounds
Related alkanamines	Ethylamine Propylamine Isopropylamine 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). Infobox references

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:

${\displaystyle {\ce {NH3 + CH2=C(CH3)2-> H2NC(CH3)3}}}$

The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste. ^[1]

${\displaystyle {\ce {(CH3)2C=CH2 + HCN + H2O -> (CH3)3CNHCHO}}}$

${\displaystyle {\ce {(CH3)3CNHCHO + H2O -> (CH3)3CNH2 + HCO2H}}}$

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

• Borane tert-butylamine complex

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.