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Sigma-Aldrich

Phenyl benzoate

99%

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Synonym(s):
Benzoic acid phenyl ester
Linear Formula:
C6H5CO2C6H5
CAS Number:
93-99-2
Molecular Weight:
198.22
Beilstein:
1566346
EC Number:
202-293-2
MDL number:
MFCD00003072
PubChem Substance ID:
24848534
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

bp

298-299 °C (lit.)

mp

68-70 °C (lit.)

solubility

alcohol: freely soluble (hot)
diethyl ether: slightly soluble
water: insoluble

SMILES string

O=C(Oc1ccccc1)c2ccccc2

InChI

1S/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H

InChI key

FCJSHPDYVMKCHI-UHFFFAOYSA-N

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General description

Phenyl benzoate is a phenyl ester of benzoic acid. Crystal structure of phenyl benzoate has been determined from 844 microdensitometer-measured intensities. All bond lengths and angles were reported to be normal. Phenyl benzoate undergoes Fries rearrangement catalyzed by heteropoly acids to yield the acylated phenols and esters.

Phenyl benzoate serves as a precursor that undergoes the intramolecular biaryl coupling reaction to produce the intermediate for the synthesis of (−)-steganone.

Application

Phenyl benzoate was used in the synthesis of soluble polyimides using dianhydride/diamine derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 - H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kaoru Matsushita et al.
Chemistry, an Asian journal, 13(17), 2393-2396 (2018-05-03)
A decarbonylative C-H coupling of azoles and aromatic esters by palladium catalysis is described. Our previously reported Ni-catalyzed C-H coupling of azoles and aromatic esters has a significant drawback regarding the substrate scope. Herein, we employ palladium catalysis instead of
Intramolecular biaryl coupling reaction of benzyl benzoate and phenyl benzoate derivatives, and its application to the formal synthesis of (-)-steganon
Takeda S, et al.
Tetrahedron, 63, 396-408 (2007)
Daun Jung et al.
Journal of applied toxicology : JAT, 36(9), 1129-1136 (2015-12-23)
In vitro testing methods for classifying sensitizers could be valuable alternatives to in vivo sensitization testing using animal models, such as the murine local lymph node assay (LLNA) and the guinea pig maximization test (GMT), but there remains a need
Fries rearrangement of aryl esters catalysed by heteropoly acid.
Kozhevnikova EF, et al.
Applied Catalysis A: General, 245(1), 69-78 (2003)
SYNTHESIS OF SOLUBLE HIGH Tg POLYIMIDES UTILIZING ESTER-ACID DIANHYDRIDE DERIVATIVES.
Moy TM, et al.
Advances in Polyimide Science and Technology: Proceedings of the Fourth International Conference on Polyimides (1993)
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Articles

Fries Rearrangement

The Fries rearrangement reaction is an organic name reaction which involves the conversion of phenolic esters into hydroxyaryl ketones on heating in the presence of a catalyst. Suitable catalysts for this reaction are Brønsted or Lewis acids such as HF, AlCl3, BF3, TiCl4, or SnCl4. The Fries rearrangement reaction is an ortho, para-selective reaction, and is used in the preparation of acyl phenols. This organic reaction has been named after German chemist Karl Theophil Fries.

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