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Sigma-Aldrich

Phenylbenzoat

99%

Synonym(e):

Phenyl-benzoat

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About This Item

Lineare Formel:
C6H5CO2C6H5
CAS-Nummer:
93-99-2
Molekulargewicht:
198.22
Beilstein:
1566346
EG-Nummer:
202-293-2
MDL-Nummer:
MFCD00003072
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24848534
NACRES:
NA.22

Assay

99%

Form

solid

bp

298-299 °C (lit.)

mp (Schmelzpunkt)

68-70 °C (lit.)

Löslichkeit

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

InChIKey

FCJSHPDYVMKCHI-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302,H315

Gefahreneinstufungen

Acute Tox. 4 Oral - Skin Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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
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)
The crystal structure of phenyl benzoate.
Adams JM and Morsi SE.
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, 32(5), 1345-1347 (1976)
Fries rearrangement of aryl esters catalysed by heteropoly acid.
Kozhevnikova EF, et al.
Applied Catalysis A: General, 245(1), 69-78 (2003)
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
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Artikel

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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