102-19-2

Basic information

• Product Name: Isopentyl phenylacetate
• Synonyms: PHENYLACETIC ACID ISOAMYL ESTER;PHENYLACETIC ACID ISOPENTYL ESTER;METHYL BUTYL PHENYL ACETATE;ISOPENTYL PHENYLACETATE;ISOAMYL PHENYLACETATE;ISOAMYL ALPHA-TOLUATE;FEMA 2081;3-METHYLBUTYL PHENYLACETATE
• CAS NO: 102-19-2
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• EINECS: 203-012-6
• Mol File: 102-19-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 268 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless oily liquid
• Density: 0.98
• Vapor Pressure: 0.00528mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Water Solubility: 63.049mg/L at 25℃
• CAS DataBase Reference: Isopentyl phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopentyl phenylacetate(102-19-2)
• EPA Substance Registry System: Isopentyl phenylacetate(102-19-2)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: AJ2945000
• Hazardous Substances Data: 102-19-2(Hazardous Substances Data)

Usage

Description

Isoamyl phenylacetate has a sweet, pleasant odor reminiscent of cocoa with a slight birch-tar undertone. May be prepared by esterification of phenylacetic acid with isoamyl alcohol in the presence of concentrated sulfuric acid; by heating benzyl nitrile and isoamyl alcohol in the presence of excess concentrated H2S04.

Chemical Properties

Isoamyl phenylacetate has a sweet, pleasant odor reminiscent of cocoa with a slight birch-tar undertone

Occurrence

Reported found in peppermint oil.

Preparation

By esterification of phenylacetic acid with isoamyl alcohol in the presence of concentrated sulfuric acid; by heating benzyl nitrile and isoamyl alcohol in the presence of excess concentrated H2SO4

Aroma threshold values

Aroma characteristics at 1%: sweet, honey, chocolate with a rosy floral nuance.

Taste threshold values

Taste characteristics at 5 to 10 ppm: warm rosy honey with phenyl chocolate nuances and dried fruit notes.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C13H18O2/c1-11(2)8-9-15-13(14)10-12-6-4-3-5-7-12/h3-7,11H,8-10H2,1-2H3

Upstream product

• 103-82-2 phenylacetic acid 
• 123-51-3 i-Amyl alcohol 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 5421-04-5 isopentyl 2-hydroxy-2-phenylacetate 

Relevant articles and documents

Structure activity relationship of organic alcohol and esters for antidepressant-like activity

The synthesized compounds 1-7 were evaluated for their antidepressant activity, among which 2-phenylethyl alcohol 1 and isoamyl phenylacetate 3 showed 43 % and 37 % reduction in immobility time in mice using forced swim test, thereby, displaying antidepressant-like activity. Compound 1 and 3 were equipotent and both these compounds were 2x effective than the standard drug phenelzine. Considering other esters it appears that a decrease in alkyl chain length or addition of either NO2 or OH groups to the phenyl ring caused a marked decline in the antidepressant-like activity.

Esterification in dry media using ferric perchlorate adsorbed on silica gel

Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic grade silica gel in the presence of alcohol ( to be used for esterification ) produces a supported reagent, Fe(ClO4)3(ROH)6/SiO2. This reagent, has been found effective for the rapid and high yield of esters, on grinding in the presence of carboxylic acids using pestle and mortar in the solid state.

Transesterification of methyl arylacetates wtih lithium alkoxides

A series of methyl arylacetates were transesterified in excellent yields using lithium alkoxides derived from primary, secondary, and tertiary aliphatic alcohols, benzyl alcohols, and allyl alcohol.