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Contents

   



(Top)
 


1 Synthesis and reactions  





2 Uses  





3 Safety  





4 References  





5 External links  














n-Butylamine






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From Wikipedia, the free encyclopedia
 


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

    CAS Number

    3D model (JSmol)

    Abbreviations NBA

    Beilstein Reference

    605269
    ChEBI
    ChEMBL
    ChemSpider
    DrugBank
    ECHA InfoCard 100.003.364 Edit this at Wikidata
    EC Number
    • 203-699-2

    Gmelin Reference

    1784
    MeSH n-butylamine

    PubChem CID

    RTECS number
    • EO29750002
    UNII
    UN number 1125

    CompTox Dashboard (EPA)

    • InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 checkY

      Key: HQABUPZFAYXKJW-UHFFFAOYSA-N checkY

    • 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−1kg−1
    Basicity (pKb) 3.22

    Magnetic susceptibility (χ)

    -58.9·10−6cm3/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
    fH298)

    −128.9–−126.5 kJ mol−1

    Std enthalpy of
    combustion
    cH298)

    −3.0196–−3.0174 MJ mol−1
    Hazards
    GHS labelling:

    Pictograms

    GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark

    Signal word

    Danger

    Hazard statements

    H225, H302, H312, H314, H332

    Precautionary statements

    P210, P280, P305+P351+P338, P310
    NFPA 704 (fire diamond)
    NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
    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)
  • [2]

    LCLo (lowest published)

    4000 ppm (rat, 4 hr)
    263 ppm (mouse, 2 hr)[2]
    NIOSH (US health exposure limits):

    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]
    Safety data sheet (SDS) hazard.com
    Related compounds

    Related alkanamines

  • 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 checkY☒N ?)

    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 aminesofbutane, 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

    [edit]

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

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

    n-Butylamine is a weak base. The pKa 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

    [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 plasticizerofnylon. 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

    [edit]

    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

    [edit]
    1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0079". National Institute for Occupational Safety and Health (NIOSH).
  • ^ a b "N-Butylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  • ^ PubChem. "Butylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-02-15.
  • ^ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  • ^ 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.
  • ^ 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
  • ^ "n-Butylamine MSDS" (PDF). Archived from the original (PDF) on 2013-11-12. Retrieved 2013-11-12.
  • ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  • [edit]
    Retrieved from "https://en.wikipedia.org/w/index.php?title=N-Butylamine&oldid=1231994443"

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