122-43-0

Basic information

• Product Name: BUTYL PHENYLACETATE
• Synonyms: Acetic acid, phenyl-, butyl ester;Benzeneaceticacid,butylester;Butyl benzene acetate;butylbenzeneacetate;phenyl-aceticacibutylester;Phenylethanoic acid butyl ester;phenylethanoicacidbutylester;N-BUTYL PHENYLACETATE
• CAS NO: 122-43-0
• Molecular Formula: C12H16O2
• Molecular Weight: 192.25
• EINECS: 204-543-6
• Product Categories: A-B;Alphabetical Listings;Flavors and Fragrances
• Mol File: 122-43-0.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 133-135 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White powder
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• CAS DataBase Reference: BUTYL PHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: BUTYL PHENYLACETATE(122-43-0)
• EPA Substance Registry System: BUTYL PHENYLACETATE(122-43-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: AJ2480000
• Hazardous Substances Data: 122-43-0(Hazardous Substances Data)

Usage

Chemical Properties

Butyl phenylacetate has pleasant rose- and honey-like odor.

Occurrence

Reported found in mountain papaya.

Preparation

By direct esterification of the acid with n-butyl alcohol in the presence of gaseous HCl.

Taste threshold values

Taste characteristics at 5 ppm: honey, sweet, chocolate, floral and rose-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3318, 1974 DOI: 10.1021/jo00937a003Tetrahedron Letters, 25, p. 3791, 1984 DOI: 10.1016/S0040-4039(01)91168-2

Safety Profile

Low toxicity by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

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

Upstream product

• 109-65-9 1-bromo-butane 
• 103-82-2 phenylacetic acid 
• 688-74-4 boric acid tributyl ester 
• 201230-82-2 carbon monoxide 
• 100-39-0 benzyl bromide 
• 140-29-4 phenylacetonitrile 
• 71-36-3 butan-1-ol 
• 103-80-0 phenylacetyl chloride 
• 100-44-7 benzyl chloride 
• 61049-78-3 S-pyridin-2-yl 2-phenylethanethioate 
• 24406-16-4 lithium di-n-butylcuprate 
• 628-81-9 butyl ethyl ether 
• 142-96-1 dibutyl ether 
• 592-84-7 n-butyl formate 

Downstream Products

• 119656-72-3 (R)-mandelic acid n-butyl ester 
• 74879-33-7 (S)-mandelic acid n-butyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 102-16-9 benzyl 2-phenylacetate 
• 56424-18-1 1-Fluor-1-phenyl-essigsaeurebutylester 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 360-03-2 2,2-Difluoro-2-phenylacetic acid 
• 60-12-8 2-phenylethanol 
• 101-97-3 Ethyl 2-phenylethanoate 
• 122-45-2 phenylacetic acid octyl ester 
• 102-13-6 2-methylpropyl phenylacetate 
• 103-82-2 phenylacetic acid 
• 15895-94-0 butyl 2-phenylacrylate 
• 5524-55-0 n-butyl 2-oxo-2-phenylacetate 

Relevant articles and documents

Solid-Phase Synthesis of Phosphorothioate Oligonucleotides Using Sulfurization Byproducts for in Situ Capping

Oligonucleotides containing phosphorothioate (PS) linkages have recently demonstrated significant clinical utility. PS oligonucleotides are manufactured via a solid-phase chain elongation process in which a four-reaction cycle consisting of detritylation, coupling, sulfurization, and failure sequence capping with Ac2O is repeated. In the capping step, uncoupled sequences are acetylated at the 5′-OH to stop the chain growth and control the levels of deletion, or (n-1), impurities. Herein, we report that the byproducts of commonly used sulfurization reagents react with the 5′-OH and cap the failure sequences. The standard Ac2O capping step can therefore be eliminated, and this 3-reaction cycle process affords a higher yield and higher or comparable overall purity compared to the conventional 4-reaction synthesis. This improvement results in reducing the number of reactions from ～80 to ～60 for the synthesis of a typical length 20-mer oligonucleotide. For every kilogram of an oligonucleotide intermediate synthesized, > 500 L of reagents and organic solvents is saved, and the E-factor is decreased to 1500 from ～2000.

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Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.