Isoamyl acetate

Isoamyl acetate

Names
Preferred IUPAC name 3-Methylbutyl acetate
Systematic IUPAC name 3-Methylbutyl ethanoate
Other names Isopentyl acetate Isopentyl ethanoate Isoamyl acetate Banana oil Pear essence
Identifiers
CAS Number	123-92-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:31725 Y
ChEMBL	ChEMBL42013 Y
ChemSpider	29016 Y
ECHA InfoCard	100.004.240
KEGG	C12296 Y
UNII	Z135787824 Y
InChI InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3 Y Key: MLFHJEHSLIIPHL-UHFFFAOYSA-N Y InChI=1/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3 Key: MLFHJEHSLIIPHL-UHFFFAOYAI
SMILES O=C(OCCC(C)C)C
Properties
Chemical formula	C7H14O2
Molar mass	130.19 g·mol−1
Appearance	Colorless liquid
Odor	Banana-like
Density	0.876 g/cm3
Melting point	−78 °C (−108 °F; 195 K)
Boiling point	142 °C (288 °F; 415 K)
Solubility in water	0.3% (20 °C)
Vapor pressure	4 mmHg (20 °C)
Magnetic susceptibility (χ)	-89.4·10−6 cm3/mol
Hazards
NFPA 704	3 1 0
Flash point	25 °C (77 °F; 298 K)
Explosive limits	1.0% (100 °C) - 7.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	7422 mg/kg (rabbit, oral) 16,600 mg/kg (rat, oral)
LCLo (lowest published)	6470 ppm (cat)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 100 ppm (525 mg/m3)
REL (Recommended)	TWA 100 ppm (525 mg/m3)
IDLH (Immediate danger)	1000 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the ester formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is also described as similar to both banana and pear.Banana oil may be either pure isoamyl acetate, or flavorings that are mixtures of isoamyl acetate, amyl acetate, and other flavors.

Isoamyl acetate is prepared by the acid catalyzed reaction (Fischer esterification) between isoamyl alcohol and glacial acetic acid as shown in the reaction equation below. Typically, sulfuric acid is used as the catalyst. Alternately, an acidic ion exchange resin can be used as the catalyst.

Isoamyl acetate is used to confer banana flavor in foods. Pear oil commonly refers to a solution of isoamyl acetate in ethanol that is used as an artificial flavor.

It is also used as a solvent for some varnishes and nitrocellulose lacquers. As a solvent and carrier for materials such as nitrocellulose, it was extensively used in the aircraft industry for stiffening and wind-proofing fabric flying surfaces, where it and its derivatives were generally known as 'aircraft dope'. Now that most aircraft are all-metal, such use is now mostly limited to historically accurate reproductions and scale models. In addition, isoamyl acetate serves as an alarm pheromone in honey bees.