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n - B u t y l a m i n e
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n -Butylamine
Names
Preferred IUPAC name
Other names
Monobutylamine
Identifiers
CAS Number
3D model (JSmol )
Abbreviations
NBA
Beilstein Reference
605269
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.003.364
EC Number
Gmelin Reference
1784
MeSH
n-butylamine
PubChem CID
RTECS number
UNII
UN number
1125
CompTox Dashboard (EPA )
InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 Y
Key: HQABUPZFAYXKJW-UHFFFAOYSA-N Y
Properties
Chemical formula
C 4 H 11 N
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 (k H )
570 μmol Pa−1 kg −1
Basicity (p K b )
3.22
Magnetic susceptibility (χ)
-58.9·10−6 cm 3 /mol
Refractive index (n D )
1.401
Viscosity
500 µPa s (at 20 °C)
Thermochemistry
Heat capacity (C )
188 J K−1 mol−1
Std enthalpy of formation (Δf H ⦵ 298 )
−128.9–−126.5 kJ mol−1
Std enthalpy of combustion (Δc H ⦵ 298 )
−3.0196–−3.0174 MJ mol−1
Hazards
GHS labelling :
Pictograms
Signal word
Danger
Hazard statements
H225 , H302 , H312 , H314 , H332
Precautionary statements
P210 , P280 , P305+P351+P338 , P310
NFPA 704 (fire diamond)
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):
LD 50 (median dose )
626 mg kg−1 (dermal, rabbit)
430 mg kg−1 (oral, mouse)
430 mg kg−1 (oral, guinea pig)
[2]
LC Lo (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).
Infobox references
Chemical compound
n -Butylamine is an organic compound (specifically, an amine ) with the formula CH3 (CH 2 )3 NH 2 . 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]
Synthesis and reactions
[ edit ]
It is produced by the reaction of ammonia and alcohols over alumina :
CH 3 (CH 2 )3 OH + NH3 → CH3 (CH 2 )3 NH 2 + H2 O
n -Butylamine is a weak base . The pKa of [CH 3 (CH 2 )3 NH 3 ]+ 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 (NH 2 Bu )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 plasticizer of nylon . 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 LD 50 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 ]
^ 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)2 I 2 ". 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
External links
[ edit ]
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=N-Butylamine&oldid=1231994443 "
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