tert-Butylamine
| tert-Butylamine | |
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2-Methylpropan-2-amine[1] |
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Other names
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| Identifiers | |
| CAS number | 75-64-9  |
| PubChem | 6385 |
| ChemSpider | 6145 |
| EC number | 200-888-1 |
| UN number | 3286 |
| MeSH | tert-butylamine |
| ChEBI | CHEBI:44639 |
| ChEMBL | CHEMBL13782 |
| RTECS number | EO3330000 |
| Beilstein Reference | 605267 |
| Gmelin Reference | 1867 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H11N |
| Molar mass | 73.14 g mol−1 |
| Appearance | Colorless liquid |
| Odor | fishy, ammoniacal |
| Density | 0.696 g/mL |
| Melting point |
-68 °C, 205.65 K, -90 °F |
| Boiling point |
43-47 °C, 316-320 K, 109-116 °F |
| Solubility in water | Miscible |
| log P | 0.802 |
| Vapor pressure | 39.29 kPa (at 20 °C) |
| Refractive index (nD) | 1.377 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−151.1–−150.1 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−2.9959–−2.9951 MJ mol−1 |
| Standard molar entropy S |
233.63 J K−1 mol−1 |
| Specific heat capacity, C | 191.71 J K−1 mol−1 |
| Hazards | |
| MSDS | rose-hulman.edu |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H302, H314, H331 |
| GHS precautionary statements | P210, P261, P280, P305+351+338, P310 |
| EU classification |  F  C |
| R-phrases | R11, R20/22, R35 |
| S-phrases | S16, S26, S36/37/39, S45 |
| NFPA 704 |
 4
3
0
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| Flash point | -38 °C |
| Autoignition temperature |
380 °C |
| Explosive limits | 1.7–9.8% |
| LD50 | 464 mg kg−1 (oral, rat) |
| Related compounds | |
| Related alkanamines | |
| Related compounds | 2-Methyl-2-nitrosopropane |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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)3NHCH
- (CH3)3NHCHO + 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 (N-tertbutyl-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]
- ^ "tert-butylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 7 May 2012.
- ^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_001
- ^ Kenneth N. Campbell, Armiger H. Sommers, and Barbara K. Campbell (1955), "tert'-Butylamine", Org. Synth.; Coll. Vol. 3: 148
