Sec-Butylamine

sec-Butylamine
Structural formula of (R)-sec-butylamine
Structural formula of (S)-sec-butylamine
Space-filling model of (R)-sec-Butylamine
Space-filling model of (S)-sec-Butylamine
Names
Preferred IUPAC name
Butan-2-amine
Other names
  • 2-Aminobutane
  • 2-Butanamine
  • (±)-sec-Butylamine
  • DL-sec-Butylamine
  • 1-Methylpropylamine
  • Mono-sec-butylamine
Identifiers
3D model (JSmol)
Abbreviations 2-AB
s-BuNH2
sBuNH2
sBuNH2
1361345, 1718761 (R), 1718760 (S)
ChEBI
ChemSpider
ECHA InfoCard 100.034.288 Edit this at Wikidata
EC Number
  • 237-732-7
KEGG
RTECS number
  • EO3325000
UNII
UN number 2733
  • InChI=1S/C4H11N/c1-3-4(2)5/h4H,3,5H2,1-2H3 checkY
    Key: BHRZNVHARXXAHW-UHFFFAOYSA-N checkY
  • CCC(C)N
  • (R): CC[C@@H](C)N
  • (S): CC[C@H](C)N
Properties
C4H11N
Molar mass 73.139 g·mol−1
Appearance Colorless liquid
Odor Fishy, ammoniacal
Density 0.724 g cm−3
Melting point −104.50 °C; −156.10 °F; 168.65 K
Boiling point 63 °C; 145 °F; 336 K
Miscible
1.3928
Viscosity 500 μPa s (at 20 °C)
Thermochemistry
−138.5 to −136.5 kJ mol−1
−3.0095 to −3.0077 MJ mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H225, H302, H314, H332, H400
P210, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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
3
3
0
Flash point 19 °C (66 °F; 292 K)
Lethal dose or concentration (LD, LC):
  • 152 mg kg−1 (oral, rat)
  • 2.5 g kg−1 (dermal, rabbit)
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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sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH3CH2CH(NH2)CH3. It is a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine, and isobutylamine. sec-Butylamine is chiral, this simplest chiral amine, in fact. The compounds has been resolved into individual enantiomers by formation of the diastereomeric tartrate salts.

sec-Butylamine is used in the production of some pesticides.

Bromacil, a commercial herbicide, is produced from sec-butylamine.

Safety

The LD50 (rat) for primary alkylamines is on the order of 100 – 1,000 mg/kg.

References

  1. ↑ "ICSC 0401 - sec-BUTYLAMINE".
  2. ↑ Publicover, Ernlie A.; Kolwich, Jennifer; Stack, Darcie L.; Doué, Alyssa J.; Ylijoki, Kai E. O. (2017). "Crystal structure of ( S )- sec -butylammonium L-tartrate monohydrate". Acta Crystallographica Section E: Crystallographic Communications. 73 (5): 716–719. doi:10.1107/S2056989017005448. PMC 5418791. PMID 28529783.
  3. 1 2 Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3-527-30673-2.
  4. ↑ United States Environmental Protection Agency. "Bromacil". 1996, pp. 1–11. Accessed 9 October 2012