n-Butylamine

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.

n-Butylamine
Names
Preferred IUPAC name
Butan-1-amine
Other names
  • 1-Aminobutane
  • 1-Butanamine
  • Monobutylamine
Identifiers
3D model (JSmol)
Abbreviations NBA
605269
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.364
EC Number
  • 203-699-2
1784
MeSH n-butylamine
RTECS number
  • EO29750002
UNII
UN number 1125
Properties
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
Miscible
log P 1.056
Vapor pressure 9.1 kPa (at 20 °C)
570 μmol Pa−1 kg−1
Basicity (pKb) 3.22
-58.9·10−6 cm3/mol
1.401
Viscosity 500 µPa s (at 20 °C)
Thermochemistry
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
Safety data sheet hazard.com
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H302, H312, H314, H332
P210, P280, P305+351+338, P310
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point −7 °C (19 °F; 266 K)
312 °C (594 °F; 585 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
  • 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]
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]
Related compounds
Related alkanamines
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

Synthesis and reactions

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

CH3(CH2)3OH + NH3 → CH3(CH2)3NH2 + H2O

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 [CH3(CH2)3NH3]+ is 10.78.[3]

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.[4][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,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]

Butylamine is a precursor to the fungicide benomyl.

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]

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References
  1. "N-Butylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  2. NIOSH Pocket Guide to Chemical Hazards. "#0079". National Institute for Occupational Safety and Health (NIOSH).
  3. H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79: 5441–5444. doi:10.1021/ja01577a030.
  4. Yin, Xi; Shi, Miao; Wu, Jianbo; Pan, Yung-Tin; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (11 September 2017). "Quantitative Analysis of Different Formation Modes of Platinum Nanocrystals Controlled by Ligand Chemistry". Nano Letters. 17 (10): 6146–6150. doi:10.1021/acs.nanolett.7b02751. PMID 28873317.
  5. Yin, Xi; Shi, Miao; Kwok, Kam Sang; Zhao, Haidong; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (22 May 2018). "Dish-like higher-ordered palladium nanostructures through metal ion-ligand complexation". Nano Research. 11 (6): 3442–3452. doi:10.1007/s12274-018-1993-0.
  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
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