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{{DISPLAYTITLE:''n''-Butylamine}} {{DISPLAYTITLE:''n''-Butylamine}}
{{chembox {{Chembox
| Watchedfields = changed |Verifiedfields = changed
|Watchedfields = changed
| verifiedrevid = 398782308
|verifiedrevid = 412364052
| Name = ''n''-Butylamine
| ImageFile = N-Butylamine.svg |Name = ''n''-Butylamine
|ImageFile = N-Butylamine.svg
| ImageSize = 150px
|ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName = ''n''-Butylamine
|ImageSize = 200
| IUPACName = butan-1-amine
|ImageName = Skeletal formula of ''n''-butylamine
| OtherNames = NBA; Monobutylamime; 1-Butanamine; 1-Aminobutane
|ImageFile1 = N-butylamine-from-xtal-1994-3D-balls.png
| Section1 = {{Chembox Identifiers
| SMILES = NCCCC |ImageSize1 = 180
|ImageAlt1 = Ball-and-stick model of the ''n''-butylamine molecule
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|PIN = Butan-1-amine
| ChemSpiderID = 7716
|OtherNames = {{Unbulleted list|1-Aminobutane|1-Butanamine|Monobutylamine
| PubChem = 8007
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 13968
| InChI = 1/C4H11N/c1-2-3-4-5/h2-5H2,1H3
| InChIKey = HQABUPZFAYXKJW-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HQABUPZFAYXKJW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-73-9
| RTECS =
| UNNumber = UN 1125
}}
| Section2 = {{Chembox Properties
|C=4|H=11|N=1
| Appearance = Colorless liquid
| Density = 0.74 g/cm<sup>3</sup>
| Solubility = Miscible
| MeltingPtC = -49
| BoilingPtC = 77
| pKa = 10.59<ref>{{cite journal | doi = 10.1021/ja01577a030 | author = Hall, H.K. | journal = J. Am. Chem. Soc. | year = 1957 | volume = 79 | pages = 5441}}</ref>
| Viscosity = 0.5 ] at 20 °C
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| MainHazards = Corrosive, if touched an cause smelling and taste problems and Highly flammable
| FlashPt = -14 °C
| RPhrases = {{R11}} {{R35}} {{R20}} {{R21}} {{R22}}
| SPhrases = {{S3}} {{S16}} {{S26}} {{S29}} {{S45}} {{S36}} {{S37}} {{S39}}
}}
| Section8 = {{Chembox Related
| OtherCpds = ]<br />]<br />]<br />]<br />]
}}
}} }}
|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<sup>−1</sup>
|MeltingPtK = 224
|BoilingPtK = 350 to 352
|Solubility = Miscible
|LogP = 1.056
|VaporPressure = 9.1 kPa (at 20&nbsp;°C)
|HenryConstant = 570 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
|pKb = 3.22
|RefractIndex = 1.401
|Viscosity = 500 µPa s (at 20&nbsp;°C)
|MagSus = -58.9·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = −128.9–−126.5 kJ mol<sup>−1</sup>
|DeltaHc = −3.0196–−3.0174 MJ mol<sup>−1</sup>
|HeatCapacity = 188 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
|ExternalSDS =
|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<sup>−1</sup> <small>(oral, rat)</small>|626 mg kg<sup>−1</sup> <small>(dermal, rabbit)</small>|430 mg kg<sup>−1</sup> <small>(oral, mouse)</small>|430 mg kg<sup>−1</sup> <small>(oral, guinea pig)</small>}}<ref name=IDLH>{{IDLH|109739|N-Butylamine}}</ref>
|PEL = C 5 ppm (15 mg/m<sup>3</sup>) <ref name=NIOSH>{{PGCH|0079}}</ref>
|IDLH = 300 ppm<ref name=NIOSH/>
|REL = C 5 ppm (15 mg/m<sup>3</sup>) <ref name=NIOSH/>
|LCLo = 4000 ppm (rat, 4 hr)<br/>263 ppm (mouse, 2 hr)<ref name=IDLH/>
}}
|Section5={{Chembox Related
|OtherFunction_label = alkanamines
|OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]|]}}
|OtherCompounds = ]
}}
}}
'''''n''-Butylamine''' is an organic compound (specifically, an ]) with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>. This colourless liquid is one of the four ]ic ]s of ], the others being ], ], and ]. 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==
'''''n''-Butylamine''' is an organic compound (specifically, an ]) with the formula CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>. This colourless liquid is one of the four ]ic ]s of ], the others being ], ] and ]. At standard temperature and pressure, ''n''-butylamine 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.
It is produced by the reaction of ammonia and alcohols over ]:
:CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>OH + NH<sub>3</sub> → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub> + H<sub>2</sub>O

''n''-Butylamine is a ]. The pK<sub>a</sub> of <sup>+</sup> 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''-.<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== ==Uses==
].]]
This compound is used as an ingredient in the manufacture of ]s (such as ]s), ]s, and ]s. It is also a precursor for the manufacture of N,N'-dibutylthio], a rubber ] accelerator, and n-butylbenzenesulfonamide, a ] of ].
This compound is used as an ingredient in the manufacture of ]s (such as ]s), ]s, and ]s. It is also a precursor for the manufacture of ], a rubber ] accelerator, and ''n''-butylbenzenesulfonamide, a ] of ]. It is used in the synthesis of ], the fungicide ], and ], and the ] ].<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 ] 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 ] and ] have set occupational exposure limits at a ceiling of 5 ppm (15 mg/m<sup>3</sup>) for dermal exposure.<ref></ref>


==References== ==References==
{{reflist}} {{Reflist}}


==External links==
{{DEFAULTSORT:Butylamine, n-}}
*{{Commonscatinline|N-Butylamine}}
]


{{DEFAULTSORT:Butylamine, n-}}
]
]
]
]
]
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]
]

Latest revision as of 12:38, 7 December 2024

n-Butylamine
Skeletal formula of 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
  • InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3Key: HQABUPZFAYXKJW-UHFFFAOYSA-N
SMILES
  • CCCCN
Properties
Chemical formula C4H11N
Molar mass 73.139 g·mol
Appearance Colorless liquid
Odor fishy, ammoniacal
Density 740 mg ml
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 kg
Basicity (pKb) 3.22
Magnetic susceptibility (χ) -58.9·10 cm/mol
Refractive index (nD) 1.401
Viscosity 500 µPa s (at 20 °C)
Thermochemistry
Heat capacity (C) 188 J K mol
Std enthalpy of
formation (ΔfH298) 		−128.9–−126.5 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−3.0196–−3.0174 MJ mol
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 (oral, rat)
  • 626 mg kg (dermal, rabbit)
  • 430 mg kg (oral, mouse)
  • 430 mg kg (oral, guinea pig)
LCLo (lowest published) 4000 ppm (rat, 4 hr)
263 ppm (mouse, 2 hr)
NIOSH (US health exposure limits):
PEL (Permissible) C 5 ppm (15 mg/m)
REL (Recommended) C 5 ppm (15 mg/m)
IDLH (Immediate danger) 300 ppm
Safety data sheet (SDS) hazard.com
Related compounds
Related alkanamines
Related compounds 2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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 is 10.78.

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-.

Uses

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.

Safety

The LD50 to rats through the oral exposure route is 366 mg/kg.

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/m) for dermal exposure.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0079". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "N-Butylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. PubChem. "Butylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-02-15.
  4. H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  5. 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.
  6. 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
  7. "n-Butylamine MSDS" (PDF). Archived from the original (PDF) on 2013-11-12. Retrieved 2013-11-12.
  8. CDC - NIOSH Pocket Guide to Chemical Hazards

External links

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