N-Butylamine

Last updated
n-Butylamine
N-Butylamine.svg
N-butylamine-from-xtal-1994-3D-balls.png
Names
Preferred IUPAC name
Butan-1-amine
Other names
  • 1-Aminobutane
  • 1-Butanamine
  • Monobutylamine
Identifiers
3D model (JSmol)
AbbreviationsNBA
605269
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.364 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-699-2
1784
MeSH n-butylamine
PubChem CID
RTECS number
  • EO29750002
UNII
UN number 1125
  • InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 Yes check.svgY
    Key: HQABUPZFAYXKJW-UHFFFAOYSA-N Yes check.svgY
  • CCCCN
Properties
C4H11N
Molar mass 73.139 g·mol−1
AppearanceColorless 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
Miscible
log P 1.056
Vapor pressure 9.1 kPa (at 20 °C)
570 μmol Pa−1 kg−1
Basicity (pKb)3.22
-58.9·10−6 cm3/mol
1.401
Viscosity 500 µPa s (at 20 °C)
Thermochemistry
188 J K−1 mol−1
−128.9–−126.5 kJ mol−1
−3.0196–−3.0174 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H312, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
2
3
0
Flash point −7 °C (19 °F; 266 K)
312 °C (594 °F; 585 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
  • 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)
[1]
4000 ppm (rat, 4 hr)
263 ppm (mouse, 2 hr) [1]
NIOSH (US health exposure limits):
PEL (Permissible)
C 5 ppm (15 mg/m3) [skin] [2]
REL (Recommended)
C 5 ppm (15 mg/m3) [skin] [2]
IDLH (Immediate danger)
300 ppm [2]
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 [77 °F], 100 kPa).
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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]

Contents

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. [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

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. Benomyl.png
Butylamine is a precursor to the fungicide benomyl.

Safety

The 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]

Related Research Articles

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine hydrate.

Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine, НДМГ; Несимметричный диметилгидразин (NDMG / NDMH or codenamed гептилheptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell typical for organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It is miscible with water, ethanol, and kerosene. In concentration between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock. Symmetrical dimethylhydrazine, 1,2-dimethylhydrazine is also known but is not as useful. UDMH can be oxidized in air to form many different substances, including toxic ones.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.

<span class="mw-page-title-main">Ethanolamine</span> Chemical compound

Ethanolamine is an organic chemical compound with the formula HOCH
2
CH
2
NH
2
or C
2
H
7
NO
. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. It was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

Aziridine is an organic compound consisting of the three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Diethylenetriamine</span> Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

<span class="mw-page-title-main">Diethanolamine</span> Chemical compound

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<span class="mw-page-title-main">Diethylamine</span> Chemical compound

Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

<span class="mw-page-title-main">Cyclohexylamine</span> Chemical compound

Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.

<span class="mw-page-title-main">Isopropylamine</span> Chemical compound

Isopropylamine is an organic compound, an amine. It is a hygroscopic colorless liquid with ammonia-like odor. It is miscible with water and flammable. It is a valuable intermediate in chemical industry.

Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde. It is a colourless liquid that dissolves in water and ether. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.

<i>m</i>-Xylylenediamine Chemical compound

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.

References

  1. 1 2 "N-Butylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0079". 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