Butyl acetate

For other uses, see Butyl acetate (disambiguation).

n-Butyl acetate is an organic compound with the formula CH₃CO₂(CH₂)₃CH₃. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.^[7]

n-Butyl acetate

Names
Preferred IUPAC name Butyl acetate
Systematic IUPAC name Butyl ethanoate
Other names n-Butyl acetate Acetic acid n-butyl ester Butile
Identifiers
CAS Number	123-86-4 Y
3D model (JSmol)	Interactive image
Abbreviations	BuAcO
ChEBI	CHEBI:31328 Y
ChEMBL	ChEMBL284391 Y
ChemSpider	29012 Y
ECHA InfoCard	100.004.236
EC Number	204-658-1
KEGG	C12304 Y
PubChem CID	31272
RTECS number	AF7350000
UNII	464P5N1905 Y
UN number	1123
CompTox Dashboard (EPA)	DTXSID3021982
InChI InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 Y Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N Y InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 Key: DKPFZGUDAPQIHT-UHFFFAOYAF
SMILES CCCCOC(=O)C
Properties
Chemical formula	CH3CO2(CH2)3CH3
Molar mass	116.160 g·mol−1
Appearance	Colorless liquid
Odor	Fruity
Density	0.8825 g/cm3 (20 °C)[1]
Melting point	−78 °C (−108 °F; 195 K)[1]
Boiling point	126.1 °C (259.0 °F; 399.2 K) at 760 mmHg[1]
Solubility in water	0.68 g/100 mL (20 °C)[1]
Solubility	Miscible in EtOH Soluble in acetone, CHCl3[1]
log P	1.82[1]
Vapor pressure	0.1 kPa (−19 °C) 1.66 kPa (24 °C)[1] 44.5 kPa (100 °C)[2]
Henry's law constant (kH)	0.281 L·atm/mol
Magnetic susceptibility (χ)	−77.47·10−6 cm3/mol
Thermal conductivity	0.143 W/m·K (0 °C) 0.136 W/m·K (25 °C) 0.130 W/m·K (50 °C) 0.116 W/m·K (100 °C)[1]
Refractive index (nD)	1.3941 (20 °C)[1]
Viscosity	1.002 cP (0 °C) 0.685 cP (25 °C) 0.5 cP (50 °C) 0.305 cP (100 °C)[1]
Structure
Dipole moment	1.87 D (24 °C)[1]
Thermochemistry
Heat capacity (C)	225.11 J/mol·K[2]
Std enthalpy of formation (ΔfH⦵298)	−609.6 kJ/mol[2]
Std enthalpy of combustion (ΔcH⦵298)	3467 kJ/mol[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammable
GHS labelling:
Pictograms	[3]
Signal word	Warning
Hazard statements	H226, H336[3]
Precautionary statements	P261[3]
NFPA 704 (fire diamond)	[4] 2 3 0
Flash point	22 °C (72 °F; 295 K)[4]
Autoignition temperature	370 °C (698 °F; 643 K)[4]
Threshold limit value (TLV)	150 ppm[1] (TWA), 200 ppm[1] (STEL)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	10768 mg/kg (~10.8g/kg) (rats, oral)[4]
LC50 (median concentration)	160 ppm (rat, 4 hr) 2000 ppm (rat, 4 hr) 391 ppm (rat, 4 hr) 1242 ppm (mouse, 2 hr)[5]
LCLo (lowest published)	14,079 ppm (cat, 72 min) 13,872 ppm (guinea pig, 4 hr)[5]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 150 ppm (710 mg/m3)[4]
REL (Recommended)	TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)[6]
IDLH (Immediate danger)	1700 ppm[6]
Related compounds
Related acetates	Ethyl acetate Propyl acetate Amyl acetate
Related compounds	Butanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

The other three isomers (four, including stereoisomers) of butyl acetate are isobutyl acetate, tert-butyl acetate, and sec-butyl acetate (two enantiomers).

Production and use

Butyl acetate is commonly manufactured by the Fischer esterification of butanol and acetic acid with the presence of sulfuric acid:^[7]

Butyl acetate is mainly used as a solvent for coatings and inks.^[7] It is a component of fingernail polish.^[8]

Occurrence in nature

Apples, especially of the "Red Delicious" variety, are flavored in part by this chemical. The alarm pheromones emitted by the Koschevnikov gland of honey bees contain butyl acetate.