102-13-6

Basic information

• Product Name: Phenylacetic acid isobutyl ester
• Synonyms: FEMA 2210;ISOBUTYL ALPHA-TOLUATE;ISOBUTYL PHENYLACETATE;EGLANTINE;2-METHYLPROPYL PHENYLACETATE;ACETIC ACID, PHENYL:ISOBUTYL ESTER;PHENYLACETIC ACID ISOBUTYL ESTER;2-methylpropylbenzeneacetate
• CAS NO: 102-13-6
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 203-007-9
• Product Categories: flavoring;Alphabetical Listings;Flavors and Fragrances;I-L
• Mol File: 102-13-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 253 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless liquid
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0152mmHg at 25°C
• Refractive Index: n20/D 1.487(lit.)
• CAS DataBase Reference: Phenylacetic acid isobutyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylacetic acid isobutyl ester(102-13-6)
• EPA Substance Registry System: Phenylacetic acid isobutyl ester(102-13-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: CY1681950
• TSCA: Yes
• Hazardous Substances Data: 102-13-6(Hazardous Substances Data)

Usage

Description

Phenylacetic acid isobutyl ester, also known as isobutyl phenylacetate, is a colorless liquid with a sweet, musk-like fragrance and a sweet, honey-like flavor. It is prepared via esterification of phenylacetic acid with isobutyl alcohol and is soluble in most fixed oils but insoluble in glycerol, mineral oil, and propylene glycol. It has a honey-like odor and is combustible.

Uses

Used in Flavoring Industry:
Phenylacetic acid isobutyl ester is used as a flavoring agent for its sweet, honey-like taste and cocoa, fruity, and waxy flavor characteristics with a spicy nuance at 4 ppm. It is commonly used to enhance the flavor of various food products.
Used in Perfume Industry:
Phenylacetic acid isobutyl ester is used as a fragrance ingredient in perfumes due to its sweet, musk-like fragrance. It adds a pleasant and long-lasting scent to perfumes and other fragranced products.
Occurrence:
Phenylacetic acid isobutyl ester has been reported to be found in cocoa, indicating its natural presence in some food sources.

Preparation

By esterification of phenylacetic acid with isobutyl alcohol.

Biochem/physiol Actions

Taste at 5 ppm

InChI:InChI=1/C12H16O2/c1-3-10(2)14-12(13)9-11-7-5-4-6-8-11/h4-8,10H,3,9H2,1-2H3

Upstream product

• 103-82-2 phenylacetic acid 
• 78-83-1 2-methyl-propan-1-ol 
• 140-29-4 phenylacetonitrile 
• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 103-80-0 phenylacetyl chloride 
• 101-41-7 benzeneacetic acid methyl ester 
• 122-45-2 phenylacetic acid octyl ester 
• 122-43-0 butyl phenylacetate 
• 100-39-0 benzyl bromide 

Downstream Products

• 60784-59-0 cyclohexylmethyl isobutyl ester 
• 167700-96-1 (4-nitro-phenyl)-acetic acid isobutyl ester 
• 31197-67-8 iso-butyl 2-oxo-2-phenylacetate 
• 103-82-2 phenylacetic acid 
• 78-83-1 2-methyl-propan-1-ol 
• 124-38-9 carbon dioxide 
• 7332-98-1 tert-butyl phenylglyoxylate 
• 100-52-7 benzaldehyde 
• 67-64-1 acetone 

Relevant articles and documents

Ruthenium Complex catalysed Condensation of Nitriles with Alcohols

The catalysed condensation of nitriles with alcohols in the presence of 1-2 equiv. of water proceeds under neutral conditions to give the corresponding esters and lactones highly efficiently along with evolution of ammonia.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

PROCESS FOR SYNTHESIZING PHENYLACETIC ACID BY CARBONYLATION OF TOLUENE

A production process for substituted phenylacetic acids or ester analogues thereof is disclosed. In this process toluene or toluene substituted with various substituents, an alcohol, an oxidant and carbon monoxide are used as raw materials to obtain compounds comprising structure of phenylacetic acid ester or analogues thereof by catalysis of the complex catalyst formed from transition metal and ligand, and such compounds are hydrolyzed to obtain various substituted phenylacetic acid based compounds. This type of compounds and their derivatives serve as important fine chemicals used widely in the industries of pharmaceuticals, pesticides, perfume and the like.