N-Butylamine


n-Butylamine is an organic compound with the formula CH33NH2. 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.

Synthesis and reactions

It is produced by the reaction of ammonia and alcohols over alumina:
n-Butylamine exhibits reactions typical of other simple alkyl amines, i.e. protonation, alkylation, acylation, condensation with carbonyls. Like other simple aliphatic amines, n-butylamine is a weak base: the pKa of + is 10.78.
n-Butylamine is also a commonly used ligand in coordination chemistry, which can coordinate with metal ions, such as Pt2+, Pd2+ ions, and form tetrabutylamine- or dibutylamine- metal complexes.

Uses

This compound is used as an ingredient in the manufacture of pesticides, pharmaceuticals, and emulsifiers. It is also a precursor for the manufacture of N,N′-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.
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Safety

The LD50 to rats through the oral exposure route is 366 mg/kg.
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 for dermal exposure.