sec-Butyl acetate

*sec*-Butyl acetate
Names
	Preferred IUPAC name Butan-2-yl acetate
	Other names 2-Butyl acetate; sec-Butyl ester; s-Butyl acetate; sec-Butyl ester of acetic acid; 1-Methylpropyl acetate;
Identifiers
CAS Number	105-46-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	7472 ;
ECHA InfoCard	100.003.001
PubChem CID	7758;
UNII	UVH2QII6CG ;
CompTox Dashboard (EPA)	DTXSID0047612 ;
	InChI InChI=1S/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3 Key: DCKVNWZUADLDEH-UHFFFAOYSA-N ; InChI=1/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3 Key: DCKVNWZUADLDEH-UHFFFAOYAV;
	SMILES O=C(OC(C)CC)C;
Properties
Chemical formula	C6H12O2
Molar mass	116.160 g·mol−1
Appearance	Clear, liquid
Odor	Fruity
Density	0.87 g/cm3, liquid
Melting point	−99 °C (−146 °F; 174 K)
Boiling point	112 °C (234 °F; 385 K)
Solubility in water	0.80 g/100 mL
Vapor pressure	10 mmHg
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
Flash point	17 °C; 62 °F; 290 K
Explosive limits	1.7–9.8%
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (950 mg/m3)
REL (Recommended)	TWA 200 ppm (950 mg/m3)
IDLH (Immediate danger)	1700 ppm
Safety data sheet (SDS)	External MSDS
	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-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose.^[3] It is a clear flammable liquid with a sweet smell.^[4]

sec-Butyl acetate has three isomers that are also acetate esters: n-butyl acetate, isobutyl acetate, and tert-butyl acetate.

History

The first method of production of sec-butyl acetate was the esterification of sec-butanol and acetic anhydride^[5] It was experimentally determined and published in 1946 by Rolf Altschul.^[6]

Toxicology

The LD₅₀ for rats is 13 g/kg.^[7] Exposure in humans to significant quantities of sec-butyl acetate can cause irritation to the eyes, mouth, throat, nose, and skin.^[8] Ingestion and inhalation of sec-butyl acetate can cause central nervous system depression producing symptoms of dizziness and disorientation.^[8]

Nomenclature

sec-Butyl acetate is chiral. It has one stereocenter, carbon 2 in the sec-butyl group. The names of the two enantiomers are:

[(2S)-butan-2-yl] acetate, (+)-sec-butyl acetate
[(2R)-butan-2-yl] acetate, (-)-sec-butyl acetate

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 370. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0073". National Institute for Occupational Safety and Health (NIOSH).
^ "Acetic acid", Ullman's encyclopedia of industrial chemistry (2003, 6th ed., Vol. 1, pp. 170–171). Weinheim, Germany: Wiley-VCH.
^ Howard, H. H. (1993). sec-Butyl acetate. In Handbook of environmental fate and exposure data for organic chemists (Vol. 5, pp. 60–65). Chelsea, MI: Lewis.
^ Altschul, R. (1946). "The Reversible Esterification of Carboxylic Acids with Isobutene and Trimethylethylene. Quantitative Studies and Synthetic Applications", Journal of the American Chemical Society, 68(12), 2605–2609.
^ "sec-butyl Acetate". The Merck Index. Royal Society of Chemistry. 2013.
^ Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.
^ ^a ^b International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.

External links

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 370. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[PGCH-2] ^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0073". National Institute for Occupational Safety and Health (NIOSH).

[3] "Acetic acid", Ullman's encyclopedia of industrial chemistry (2003, 6th ed., Vol. 1, pp. 170–171). Weinheim, Germany: Wiley-VCH.

[4] Howard, H. H. (1993). sec-Butyl acetate. In Handbook of environmental fate and exposure data for organic chemists (Vol. 5, pp. 60–65). Chelsea, MI: Lewis.

[5] Altschul, R. (1946). "The Reversible Esterification of Carboxylic Acids with Isobutene and Trimethylethylene. Quantitative Studies and Synthetic Applications", Journal of the American Chemical Society, 68(12), 2605–2609.

[6] "sec-butyl Acetate". The Merck Index. Royal Society of Chemistry. 2013.

[7] Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.

[inchem-8] International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.

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