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

Description

BUTYL PHENYLACETATE is an organic compound with a pleasant roseand honey-like odor. It is characterized by its sweet, chocolate, and floral taste at a concentration of 5 ppm. BUTYL PHENYLACETATE has been reported to be found in mountain papaya.

Uses

Used in Flavor and Fragrance Industry:
BUTYL PHENYLACETATE is used as a flavoring agent for its sweet, honey, chocolate, and floral taste characteristics. Its unique taste profile makes it suitable for enhancing the flavor of various food products.
BUTYL PHENYLACETATE is also used as a fragrance ingredient for its pleasant roseand honey-like odor. It can be incorporated into perfumes, cosmetics, and other scented products to provide a desirable and long-lasting fragrance.
Used in the Perfumery Industry:
In the perfumery industry, BUTYL PHENYLACETATE is used as a fixative agent. Its ability to provide a long-lasting and pleasant scent makes it an ideal component in the formulation of perfumes and colognes. It helps to stabilize and prolong the fragrance, ensuring that the scent remains consistent and enjoyable throughout the day.

Preparation

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

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.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.