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
CAS Number	13952-84-6 ; 13250-12-9 (R) ; 513-49-5 (S) ;
3D model (JSmol)	Interactive image; (R): Interactive image; (S): Interactive image;
Abbreviations	2-AB; s-BuNH2; sBuNH2; sBuNH2
Beilstein Reference	1361345, 1718761 (R), 1718760 (S)
ChEBI	CHEBI:74526 ;
ChemSpider	23255 ; 2006669 (R) ; 5145745 (S) ;
ECHA InfoCard	100.034.288
EC Number	237-732-7;
KEGG	C18706 ;
PubChem CID	24874; 2724537 (R); 6713753 (S);
RTECS number	EO3325000;
UNII	QAZ452YGSG ; 29HC5ICB6K (R) ; Z192XWH21O (S) ;
UN number	2733
CompTox Dashboard (EPA)	DTXSID4022284 ;
	InChI InChI=1S/C4H11N/c1-3-4(2)5/h4H,3,5H2,1-2H3 Key: BHRZNVHARXXAHW-UHFFFAOYSA-N ;
	SMILES CCC(C)N; (R): CC[C@@H](C)N; (S): CC[C@H](C)N;
Properties
Chemical formula	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
Solubility in water	Miscible
Refractive index (nD)	1.3928
Viscosity	500 μPa s (at 20 °C)
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−138.5 to −136.5 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−3.0095 to −3.0077 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H332, H400
Precautionary statements	P210, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 3 0
Flash point	19 °C (66 °F; 292 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	152 mg kg−1 (oral, rat); 2.5 g kg−1 (dermal, rabbit);
Related compounds
Related alkanamines	Propylamine; Isopropylamine; Isobutylamine; tert-Butylamine; n-Butylamine;
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). verify (what is ?) Infobox references

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.^[2]

sec-Butylamine is used in the production of some pesticides.^[3]

Safety

The LD₅₀ (rat) for primary alkylamines is on the order of 100 – 1,000 mg/kg.^[3]

References

↑ "ICSC 0401 - sec-BUTYLAMINE".
↑ 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.
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.
↑ United States Environmental Protection Agency. "Bromacil". 1996, pp. 1–11. Accessed 9 October 2012

[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.

[Ullmann-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.

[EPA-4] United States Environmental Protection Agency. "Bromacil". 1996, pp. 1–11. Accessed 9 October 2012

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