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142719

Sigma-Aldrich

Phenyl benzoate

99%

Sinonimo/i:

Benzoic acid phenyl ester

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About This Item

Formula condensata:
C6H5CO2C6H5
Numero CAS:
93-99-2
Peso molecolare:
198.22
Beilstein:
1566346
Numero CE:
202-293-2
Numero MDL:
MFCD00003072
Codice UNSPSC:
12352100
ID PubChem:
24848534
NACRES:
NA.22

Saggio

99%

Forma fisica

solid

P. eboll.

298-299 °C (lit.)

Punto di fusione

68-70 °C (lit.)

Solubilità

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

Stringa SMILE

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
FCJSHPDYVMKCHI-UHFFFAOYSA-N

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Categorie correlate

Descrizione generale

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.

Applicazioni

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302,H315

Classi di pericolo

Acute Tox. 4 Oral - Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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trans-Cinnamic acid ≥99%

Sigma-Aldrich

C80857

trans-Cinnamic acid

Fluorene 98%

Sigma-Aldrich

128333

Fluorene

Fenthion PESTANAL®, analytical standard

Supelco

36552

Fenthion

Benzoic anhydride ≥95%

Sigma-Aldrich

385980

Benzoic anhydride

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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Articoli

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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