n-Butylamine

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n-Butylamine
Skeletal formula of n-butylamine
Ball-and-stick model of the N-butylamine molecule
Names
Preferred IUPAC name
Butan-1-amine
Other names
  • 1-Aminobutane
  • 1-Butanamine
  • Monobutylamine
Identifiers
3D model (JSmol)
Abbreviations NBA
605269
ChEBI
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 73.14 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
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
−128.9–−126.5 kJ mol−1
−3.0196–−3.0174 MJ mol−1
Hazards
Safety data sheet hazard.com
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H302, H312, H314, H332
P210, P280, P305+351+338, P310
NFPA 704
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., gasoline Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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)
[2]
4000 ppm (rat, 4 hr)
263 ppm (mouse, 2 hr)[2]
US health exposure limits (NIOSH):
PEL (Permissible)
C 5 ppm (15 mg/m3) [skin][1]
REL (Recommended)
C 5 ppm (15 mg/m3) [skin][1]
IDLH (Immediate danger)
300 ppm[1]
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).
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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.

Synthesis and reactions[edit]

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]

Uses[edit]

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.[4]

Butylamine is a precursor to the fungicide benomyl.

Safety[edit]

The LD50 to rats through the oral exposure route is 366 mg/kg.[5]

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.[6]

References[edit]

  1. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0079". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b "N-Butylamine". Immediately Dangerous to Life and Health. 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. ^ 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
  5. ^ n-Butylamine MSDS
  6. ^ CDC - NIOSH Pocket Guide to Chemical Hazards