N-Butylamine

{{DISPLAYTITLE:''n''-Butylamine}} {{Chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 412364052 |Name = ''n''-Butylamine |ImageFile = N-Butylamine.svg |ImageClass = skin-invert-image |ImageFile_Ref = {{chemboximage|correct|??}} |ImageSize = 200 |ImageName = Skeletal formula of ''n''-butylamine |ImageFile1 = N-butylamine-from-xtal-1994-3D-balls.png |ImageSize1 = 180 |ImageClass1 = bg-transparent |ImageAlt1 = Ball-and-stick model of the ''n''-butylamine molecule |PIN = Butan-1-amine |OtherNames = {{Unbulleted list|1-Aminobutane|1-Butanamine|Monobutylamine }} |Section1={{Chembox Identifiers |Abbreviations = NBA |CASNo = 109-73-9 |CASNo_Ref = {{cascite|correct|CAS}} |PubChem = 8007 |ChemSpiderID = 7716 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |UNII = N2QV60B4WR |UNII_Ref = {{fdacite|changed|FDA}} |EINECS = 203-699-2 |UNNumber = 1125 |DrugBank = DB03659 |DrugBank_Ref = {{drugbankcite|changed|drugbank}} |MeSHName = n-butylamine |ChEBI = 43799 |ChEBI_Ref = {{ebicite|changed|EBI}} |ChEMBL = 13968 |ChEMBL_Ref = {{ebicite|correct|EBI}} |RTECS = EO29750002 |Beilstein = 605269 |Gmelin = 1784 |SMILES = CCCCN |StdInChI = 1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = HQABUPZFAYXKJW-UHFFFAOYSA-N |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties |C=4 | H=11 | N=1 |Appearance = Colorless liquid |Odor = fishy, ammoniacal |Density = 740 mg ml−1 |MeltingPtK = 224 |BoilingPtK = 350 to 352 |Solubility = Miscible |LogP = 1.056 |VaporPressure = 9.1 kPa (at 20 °C) |HenryConstant = 570 μmol Pa−1 kg−1 |pKb = 3.22 |RefractIndex = 1.401 |Viscosity = 500 µPa s (at 20 °C) |MagSus = −58.9·10−6 cm3/mol }} |Section3={{Chembox Thermochemistry |DeltaHf = −128.9 – −126.5 kJ mol−1 |DeltaHc = −3.0196 – −3.0174 MJ mol−1 |HeatCapacity = 188 J K−1 mol−1 }} |Section4={{Chembox Hazards |ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/b6340.htm hazard.com] |GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}} |GHSSignalWord = '''DANGER''' |HPhrases = {{H-phrases|225|302|312|314|332}} |PPhrases = {{P-phrases|210|280|305+351+338|310}} |NFPA-F = 3 |NFPA-H = 2 |NFPA-R = 0 |FlashPtC = -7 |AutoignitionPtC = 312 |ExploLimits = 1.7–9.8% |LD50 = {{Unbulleted list|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)}}<ref name=IDLH>{{IDLH|109739|N-Butylamine}}</ref> |PEL = C 5 ppm (15 mg/m3) [skin]<ref name=NIOSH>{{PGCH|0079}}</ref> |IDLH = 300 ppm<ref name=NIOSH/> |REL = C 5 ppm (15 mg/m3) [skin]<ref name=NIOSH/> |LCLo = 4000 ppm (rat, 4 hr) 263 ppm (mouse, 2 hr)<ref name=IDLH/> }} |Section5={{Chembox Related |OtherFunction_label = alkanamines |OtherFunction = {{Unbulleted list|Propylamine|Isopropylamine|1,2-Diaminopropane|1,3-Diaminopropane|Isobutylamine|''tert''-Butylamine|''sec''-Butylamine|Putrescine|Pentylamine|Cadaverine}} |OtherCompounds = 2-Methyl-2-nitrosopropane }} }} '''''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.<ref>{{Cite web|last=PubChem|title=Butylamine|url=https://pubchem.ncbi.nlm.nih.gov/compound/8007|access-date=2022-02-15|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>

==Synthesis and reactions== It is produced by the reaction of ammonia and alcohols over alumina: :<chem>CH3(CH2)3OH + NH3 -> CH3(CH2)3NH2 + H2O</chem>

''n''-Butylamine is a weak base. The pKa of [CH3(CH2)3NH3]+ is 10.78.<ref>{{cite journal|author=H. K. Hall, Jr.|year=1957|journal=J. Am. Chem. Soc.|volume=79|pages=5441–5444|title=Correlation of the Base Strengths of Amines|issue=20|doi=10.1021/ja01577a030}}</ref>

''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].<ref>{{cite journal |doi=10.1016/j.ica.2003.10.039|title=Multinuclear NMR Study and Crystal Structures of Complexes of the Types ''cis''- and ''trans''-Pt(amine)''2''I''2''|year=2004|last1=Rochon|first1=Fernande D.|last2=Buculei|first2=Viorel|journal=Inorganica Chimica Acta|volume=357|issue=8|pages=2218–2230}}</ref>

==Uses== [[File:Benomyl.png|thumb|upright=0.7|left|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.<ref name=Ullmann>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}}</ref>

==Safety== The LD50 to rats through the oral exposure route is 366 mg/kg.<ref>{{Cite web |url=https://us.vwr.com/stibo/hi_res/8235547.pdf |title=''n''-Butylamine MSDS |access-date=2013-11-12 |archive-url=https://web.archive.org/web/20131112205047/https://us.vwr.com/stibo/hi_res/8235547.pdf |archive-date=2013-11-12 |url-status=dead}}</ref>

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.<ref>[https://www.cdc.gov/niosh/npg/npgd0079.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref>

==References== {{Reflist}}

==External links== *{{Commonscatinline|N-Butylamine}}

{{DEFAULTSORT:Butylamine, n-}} Category:Alkylamines Category:Butyl compounds Category:Foul-smelling chemicals