Sec-Butyl acetate

sec-Butyl acetate

Names
Preferred IUPAC name Butan-2-yl acetate[1]
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^N
3D model (JSmol)	Interactive image
ChemSpider	7472^Y
ECHA InfoCard	100.003.001
PubChem CID	7758
UNII	UVH2QII6CG^N
CompTox Dashboard (EPA)	DTXSID0047612
InChI InChI=1S/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3^Y Key: DCKVNWZUADLDEH-UHFFFAOYSA-N^Y 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[2]
Density	0.87 g/cm^3, 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[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammable
Flash point	17 °C; 62 °F; 290 K[2]
Explosive limits	1.7–9.8%[2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (950 mg/m^3)[2]
REL (Recommended)	TWA 200 ppm (950 mg/m^3)[2]
IDLH (Immediate danger)	1700 ppm[2]
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). N verify (what is ^YN ?) 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

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.
2. 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.
8. International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.

External links

• ChemExpr.com
• CDC - NIOSH Pocket Guide to Chemical Hazards