N-Butylamine
Chemical compound
From Wikipedia, the free encyclopedia
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.[3]
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| Names | |
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| Preferred IUPAC name
Butan-1-amine | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| Abbreviations | NBA |
| 605269 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.364 |
| EC Number |
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| 1784 | |
| MeSH | n-butylamine |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1125 |
CompTox Dashboard (EPA) |
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| Properties | |
| C4H11N | |
| Molar mass | 73.139 g·molâ1 |
| Appearance | Colorless liquid |
| Odor | fishy, ammoniacal |
| Density | 740 mg mlâ1 |
| Melting point | â49 °C; â56 °F; 224 K |
| Boiling point | 77 to 79 °C; 170 to 174 °F; 350 to 352 K |
| Miscible | |
| log P | 1.056 |
| Vapor pressure | 9.1 kPa (at 20 °C) |
Henry's law constant (kH) |
570 μmol Paâ1 kgâ1 |
| Basicity (pKb) | 3.22 |
| â58.9·10â6 cm3/mol | |
Refractive index (nD) |
1.401 |
| Viscosity | 500 µPa s (at 20 °C) |
| Thermochemistry | |
Heat capacity (C) |
188 J Kâ1 molâ1 |
Std enthalpy of formation (ÎfH⦵298) |
â128.9 â â126.5 kJ molâ1 |
Std enthalpy of combustion (ÎcH⦵298) |
â3.0196 â â3.0174 MJ molâ1 |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225, H302, H312, H314, H332 | |
| P210, P280, P305+P351+P338, P310 | |
| NFPA 704 (fire diamond) | |
| Flash point | â7 °C (19 °F; 266 K) |
| 312 °C (594 °F; 585 K) | |
| Explosive limits | 1.7â9.8% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
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LCLo (lowest published) |
4000 ppm (rat, 4 hr) 263 ppm (mouse, 2 hr)[1] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) |
C 5 ppm (15 mg/m3) [skin][2] |
REL (Recommended) |
C 5 ppm (15 mg/m3) [skin][2] |
IDLH (Immediate danger) |
300 ppm[2] |
| Safety data sheet (SDS) | hazard.com |
| Related compounds | |
Related alkanamines |
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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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Synthesis and reactions
It is produced by the reaction of ammonia and alcohols over alumina:
![{\displaystyle {\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}){\vphantom {A}}_{\smash[{t}]{3}}\mathrm {OH} {}+{}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{3}}{}\mathrel {\longrightarrow } {}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}){\vphantom {A}}_{\smash[{t}]{3}}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {H} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {O} }}](http://wikimedia.org/api/rest_v1/media/math/render/svg/4277a183bb33113450362dc46c5629507a50fda5)
n-Butylamine is a weak base. The pKa of [CH3(CH2)3NH3]+ is 10.78.[4]
n-Butylamine exhibits reactions typical of other simple alkyl amines, i.e., alkylation, acylation, condensation with carbonyls. It forms complexes with metal ions, examples being cis- and trans-[PtI2(NH2Bu)2].[5]
Uses
This compound is used as an ingredient in the manufacture of pesticides (such as thiocarbazides), pharmaceuticals, and emulsifiers. It is also a precursor for the manufacture of N,Nâ²-dibutylthiourea, a rubber vulcanization accelerator, and n-butylbenzenesulfonamide, a plasticizer of nylon. It is used in the synthesis of fengabine, the fungicide benomyl, and butamoxane, and the antidiabetic tolbutamide.[6]
Safety
The LD50 to rats through the oral exposure route is 366 mg/kg.[7]
In regards to occupational exposures to n-butylamine, the Occupational Safety and Health Administration and National Institute for Occupational Safety and Health have set occupational exposure limits at a ceiling of 5 ppm (15 mg/m3) for dermal exposure.[8]
