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)}}{{IDLH|109739|N-Butylamine}}
|PEL = C 5 ppm (15 mg/m3) [skin]{{PGCH|0079}}
|REL = C 5 ppm (15 mg/m3) [skin]
|LCLo = 4000 ppm (rat, 4 hr)
263 ppm (mouse, 2 hr)
}}
|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.{{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}}
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 is a weak base. The pKa of [CH3(CH2)3NH3]+ is 10.78.{{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}}
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].{{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)2I2|year=2004|last1=Rochon|first1=Fernande D.|last2=Buculei|first2=Viorel|journal=Inorganica Chimica Acta|volume=357|issue=8|pages=2218–2230}}
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.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}}
Safety
The LD50 to rats through the oral exposure route is 366 mg/kg.{{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}}
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.[https://www.cdc.gov/niosh/npg/npgd0079.html CDC - NIOSH Pocket Guide to Chemical Hazards]
References
{{Reflist}}
External links
- {{Commonscatinline|N-Butylamine}}
{{DEFAULTSORT:Butylamine, n-}}