tert-Butylamine

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tert-Butylamine
Skeletal formula of tert-butylamine
Ball and stick model of tert-butylamine
Identifiers
CAS number 75-64-9 YesY
PubChem 6385
ChemSpider 6145 YesY
EC number 200-888-1
UN number 3286
MeSH tert-butylamine
ChEBI CHEBI:44639 YesY
ChEMBL CHEMBL13782 YesY
RTECS number EO3330000
Beilstein Reference 605267
Gmelin Reference 1867
Jmol-3D images Image 1
Properties
Molecular 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
Hazards
MSDS 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
GHS hazard statements H225, H302, H314, H331
GHS precautionary statements P210, P261, P280, P305+351+338, P310
EU classification Highly Flammable F Corrosive 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
Flash point −38 °C (−36 °F; 235 K)
Explosive limits 1.7–9.8%
LD50 464 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds 2-Methyl-2-nitrosopropane
Except where noted otherwise, 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:[2]

(CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO
(CH3)3CNHCHO + H2O → (CH3)3NH2 + HCO2H

In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.[3]

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.

References[edit]

  1. ^ "tert-butylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 7 May 2012. 
  2. ^ 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
  3. ^ Kenneth N. Campbell, Armiger H. Sommers, and Barbara K. Campbell (1955), "tert'-Butylamine", Org. Synth. ; Coll. Vol. 3: 148