sec-Butylamine

*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;
Abbreviations	2-AB
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;
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 pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H302, H314, H332, H400
GHS precautionary statements	P210, P273, P280, P305+351+338, 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).

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 and therefore can exist in either of two enantiomeric forms.

sec-Butylamine is used in the production of some pesticides.^[2]

Bromacil, a commercial herbicide, is produced from sec-butylamine.^[3]

Safety

The LD50 (rat) for primary alkylamines is 100 – 1 mg/kg.^[2]

References

^ http://www.inchem.org/documents/icsc/icsc/eics0401.htm
^ ^a ^b 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.
^ United States Environmental Protection Agency. "Bromacil". 1996, pp. 1–11. Accessed 9 October 2012

[1] ttp://www.inchem.org/documents/icsc/icsc/eics0401.htm

[Ullmann-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.

[EPA-3] United States Environmental Protection Agency. "Bromacil". 1996, pp. 1–11. Accessed 9 October 2012

[1]

[2]

[3]

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
Abbreviations	2-AB
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
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^[1]
Refractive index (n_D)	1.3928
Viscosity	500 μPa s (at 20 °C)
Thermochemistry
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−138.5 to −136.5 kJ mol⁻¹
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	−3.0095 to −3.0077 MJ mol⁻¹
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H302, H314, H332, H400
GHS precautionary statements	P210, P273, P280, P305+351+338, 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).