n-Butylamine

n-Butylamine

Names
Preferred IUPAC name Butan-1-amine
Other names 1-Aminobutane 1-Butanamine Monobutylamime
Identifiers
CAS Number	109-73-9 Y
3D model (Jmol)	Interactive image
Abbreviations	NBA
Beilstein Reference	605269
ChEBI	CHEBI:43799 N
ChEMBL	ChEMBL13968 Y
ChemSpider	7716 Y
DrugBank	DB03659 N
ECHA InfoCard	100.003.364
EC Number	203-699-2
Gmelin Reference	1784
MeSH	n-butylamine
PubChem	8007
RTECS number	EO29750002
UNII	N2QV60B4WR N
UN number	1125
InChI InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 Y Key: HQABUPZFAYXKJW-UHFFFAOYSA-N Y
SMILES CCCCN
Properties
Chemical formula	C4H11N
Molar mass	73.14 g·mol−1
Appearance	Colorless liquid
Odor	fishy, ammoniacal
Density	740 mg mL−1
Melting point	−49 °C; −56 °F; 224 K
Boiling point	77 to 79 °C; 170 to 174 °F; 350 to 352 K
Solubility in water	Miscible
log P	1.056
Vapor pressure	9.1 kPa (at 20 °C)
Henry's law constant (kH)	570 μmol Pa−1 kg−1
Refractive index (nD)	1.401
Viscosity	500 µPa s (at 20 °C)
Thermochemistry
Specific heat capacity (C)	188 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−128.9–−126.5 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−3.0196–−3.0174 MJ mol−1
Hazards
Safety data sheet	hazard.com
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H302, H312, H314, H332
GHS precautionary statements	P210, P280, P305+351+338, P310
EU classification (DSD)	F C
R-phrases	R11 R20/21/22, R35
S-phrases	S3, S16, S26, S29 S36/37/39 S45
NFPA 704	3 2 0
Flash point	−7 °C (19 °F; 266 K)
Autoignition temperature	312 °C (594 °F; 585 K)
Explosive limits	1.7–9.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	366 mg kg−1 (oral, rat) 626 mg kg−1 (dermal, rabbit) 430 mg kg−1 (oral, mouse) 430 mg kg−1 (oral, guinea pig) [1]
LCLo (lowest published)	4000 ppm (rat, 4 hr) 263 ppm (mouse, 2 hr)[1]
US health exposure limits (NIOSH):
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]
Related compounds
Related alkanamines	Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine tert-Butylamine sec-Butylamine Putrescine Pentylamine Cadaverine
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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Infobox references

n-Butylamine is an organic compound (specifically, an amine) with the formula CH₃CH₂CH₂CH₂NH₂. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine and isobutylamine. At standard temperature and pressure, n-butylamine 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.

Like other simple aliphatic amines, n-butylamine is a weak base with a pK_a of 10.59 in its protonated form.^[3]

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,N'-dibutylthiourea, a rubber vulcanization accelerator, and n-butylbenzenesulfonamide, a plasticizer of nylon.

N-Butylamine was used in the synthesis of Fengabine.

Safety

The LD₅₀ to rats through the oral exposure route is 366 mg/kg.^[4]

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.^[5]

References