sec-Butylamine

sec-Butylamine

Names
IUPAC name Butan-2-amine[1]
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)
Abbreviations	2-AB
Beilstein Reference	1361345, 1718761 (R), 1718760 (S)
ChEBI	CHEBI:74526
ChemSpider	23255 2006669 (R) 5145745 (S)
EC Number	237-732-7
Jmol interactive 3D	Image
KEGG	C18706
PubChem	24874 2724537 (R) 6713753 (S)
RTECS number	EO3325000
UNII	QAZ452YGSG
UN number	2733
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	73.14 g·mol^−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
Density	724 mg mL^−1
Melting point	−104.50 °C; −156.10 °F; 168.65 K
Boiling point	63 °C; 145 °F; 336 K
Solubility in water	Miscible[2]
Refractive index (nD)	1.3928
Viscosity	500 μPa s (at 20 °C)
Thermochemistry
Std enthalpy of formation (ΔfH^o298)	−138.5–−136.5 kJ mol^−1
Std enthalpy of combustion (ΔcH^o298)	−3.0095–−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
EU classification (DSD)	F C N
R-phrases	R11, R20/22, R35, R50
S-phrases	S16, S26, S36/37/39, S45
NFPA 704	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 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine tert-Butylamine n-Butylamine Putrescine Pentylamine Cadaverine
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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Infobox references

sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH₃CH₂CH(NH₂)CH₃, and occurs as a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine and isobutylamine. It is very harmful to aquatic organisms.

sec-Butylamine is used as a fungicide^[3] and is considered a high production volume chemical. It is undergoing comprehensive review by the American Chemistry Council's Amines Panel as part of the Primary Amines Category.

Chemical structure

sec-Butylamine is one of the isomers of butylamine. It is chiral and therefore can exist in either of two enantiomeric forms.

(R)-Enantiomer (left) and (S)-enantiomer (right)

Safety

This compound is moderately toxic, as well as flammable and corrosive.

References

1. "SEC-BUTYLAMINE - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 8 May 2012.
2. http://www.inchem.org/documents/icsc/icsc/eics0401.htm
3. Butylamine, AlanWood.net