N-Butylamine

n-Butylamine

Skeletal formula of n-butylamine
Names
Preferred IUPAC name Butan-1-amine
Other names 1-Aminobutane 1-Butanamine Monobutylamine
Identifiers
CAS Number	109-73-9  Y
3D model (JSmol)	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 CID	8007
RTECS number	EO29750002
UNII	N2QV60B4WR  N
UN number	1125
CompTox Dashboard (EPA)	DTXSID1021904
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	73.139 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
Basicity (pKb)	3.22
Magnetic susceptibility (χ)	−58.9·10−6 cm3/mol
Refractive index (nD)	1.401
Viscosity	500 µPa s (at 20 °C)
Thermochemistry
Heat capacity (C)	188 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−128.9 – −126.5 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−3.0196 – −3.0174 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H314, H332
Precautionary statements	P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	2 3 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]
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	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). N  verify  (what is  YN ?) Infobox references

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]

Synthesis and reactions

It is produced by the reaction of ammonia and alcohols over alumina:

${\displaystyle {\ce {CH3(CH2)3OH + NH3 -> CH3(CH2)3NH2 + H2O}}}$

n-Butylamine is a weak base. The pK_a 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

Butylamine is a precursor to the fungicide benomyl.

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. 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]

References

1. "N-Butylamine". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
2. NIOSH Pocket Guide to Chemical Hazards. "#0079". National Institute for Occupational Safety and Health (NIOSH).
3. PubChem. "Butylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-02-15.
4. H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
5. Rochon, Fernande D.; Buculei, Viorel (2004). "Multinuclear NMR Study and Crystal Structures of Complexes of the Types cis- and trans-Pt(amine)2I2". Inorganica Chimica Acta. 357 (8): 2218–2230. doi:10.1016/j.ica.2003.10.039.
6. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi : 10.1002/14356007.a02_001
7. "n-Butylamine MSDS" (PDF). Archived from the original (PDF) on 2013-11-12. Retrieved 2013-11-12.
8. CDC - NIOSH Pocket Guide to Chemical Hazards

External links

• Media related to N-Butylamine at Wikimedia Commons