n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomericamines 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.[3]
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]
^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
^(PDF). Archived from the original (PDF) on 2013-11-12. Retrieved 2013-11-12.
Media related to N-Butylamine at Wikimedia Commons
October 21, 2023
butylamine, organic, compound, specifically, amine, with, formula, 3nh2, this, colourless, liquid, four, isomeric, amines, butane, others, being, butylamine, tert, butylamine, isobutylamine, liquid, having, fishy, ammonia, like, odor, common, amines, liquid, a. 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 3 n Butylamine NamesPreferred IUPAC name Butan 1 amineOther names 1 Aminobutane1 ButanamineMonobutylamineIdentifiersCAS Number 109 73 9 Y3D model JSmol Interactive imageAbbreviations NBABeilstein Reference 605269ChEBI CHEBI 43799 NChEMBL ChEMBL13968 YChemSpider 7716 YDrugBank DB03659 NECHA InfoCard 100 003 364EC Number 203 699 2Gmelin Reference 1784MeSH n butylaminePubChem CID 8007RTECS number EO29750002UNII N2QV60B4WR NUN number 1125CompTox Dashboard EPA DTXSID1021904InChI InChI 1S C4H11N c1 2 3 4 5 h2 5H2 1H3 YKey HQABUPZFAYXKJW UHFFFAOYSA N YSMILES CCCCNPropertiesChemical formula C 4H 11NMolar mass 73 139 g mol 1Appearance Colorless liquidOdor fishy ammoniacalDensity 740 mg ml 1Melting point 49 C 56 F 224 KBoiling point 77 to 79 C 170 to 174 F 350 to 352 KSolubility in water Misciblelog P 1 056Vapor pressure 9 1 kPa at 20 C Henry s lawconstant kH 570 mmol Pa 1 kg 1Basicity pKb 3 22Magnetic susceptibility x 58 9 10 6 cm3 molRefractive index nD 1 401Viscosity 500 µPa s at 20 C ThermochemistryHeat capacity C 188 J K 1 mol 1Std enthalpy offormation DfH 298 128 9 126 5 kJ mol 1Std enthalpy ofcombustion DcH 298 3 0196 3 0174 MJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H302 H312 H314 H332Precautionary statements P210 P280 P305 P351 P338 P310NFPA 704 fire diamond 230Flash point 7 C 19 F 266 K Autoignitiontemperature 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 comRelated compoundsRelated alkanamines PropylamineIsopropylamine1 2 Diaminopropane1 3 DiaminopropaneIsobutylaminetert Butylaminesec ButylaminePutrescinePentylamineCadaverineRelated compounds 2 Methyl 2 nitrosopropaneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis and reactions 2 Uses 3 Safety 4 References 5 External linksSynthesis and reactions EditIt is produced by the reaction of ammonia and alcohols over alumina CH3 CH2 3OH NH3 CH3 CH2 3NH2 H2On 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 EditThis 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 nbsp Butylamine is a precursor to the fungicide benomyl Safety EditThe 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 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 Hoke 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 HazardsExternal links Edit nbsp Media related to N Butylamine at Wikimedia Commons Retrieved from https en wikipedia org w index php title N Butylamine amp oldid 1168408370, wikipedia, wiki, book, books, library,
