Phenyl benzoate Chemical Properties

Melting point:

68-70 °C (lit.)

Boiling point:

298-299 °C (lit.)

Density 

1.235

refractive index 

1.5954 (estimate)

Flash point:

298-299°C

storage temp. 

Store below +30°C.

solubility 

alcohol: freely soluble (hot)

form 

Fine Crystalline Powder

color 

White

Odor

geranium odor

Water Solubility 

Soluble in ethanol, ethyl ether and chloroform. Insoluble in water.

Merck 

14,7275

BRN 

1566346

Stability:

Stable. Incompatible with strong oxidizing agents, strong acids, strong bases.

LogP

3.590

CAS DataBase Reference

93-99-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, phenyl ester(93-99-2)

EPA Substance Registry System

Benzoic acid, phenyl ester (93-99-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-38

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

DH6299500

TSCA 

Yes

HS Code 

29163100

Toxicity

LD50 orl-mus: 1225 mg/kg YKKZAJ 89,1179,69

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Phenyl benzoate Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Phenyl Benzoate is a key reagent in the synthesis of soluble polyimides using dianhydride/diamine derivatives.

Definition

ChEBI: A benzoate ester obtained by the formal condensation of phenol with benzoic acid.

Preparation

A glass tube was charged with benzoic anhydride (1.13 g, 5.00 mmol), diphenyl carbonate (1.07 g, 5.00 mmol), and either Ti(OBu)4 (0.020 g, 0.059 mmol) or Sn(OMe)2Bu2 (0.017 g, 0.059 mmol) as catalyst. The reaction mixture was heated at 300 ℃ for 30 min. After cooling to room temperature, the crude product obtained was dissolved in dichloromethane (10 mL) and the solution was filtered. The solvent was evaporated and the product obtained after column chromatography (silica gel; CH2Cl2/cyclohexane, 4:1) was recrystallized from petroleum ether; yield 95%.

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 86, 1983 DOI: 10.1139/v83-015
Synthesis, p. 908, 1983 DOI: 10.1055/s-1983-30561
Tetrahedron Letters, 41, p. 1343, 2000 DOI: 10.1016/S0040-4039(99)02289-3

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.

Safety Profile

Moderately toxic by ingestion. When heated it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the ester from EtOH using ca twice the volume needed for complete dissolution at 69o. [Beilstein 9 IV 303.]

Phenyl benzoate(93-99-2)Related Product Information

• Benzoic acid
• Benzyl benzoate
• Triphenyl phosphite
• Denatonium Benzoate Anhydrous
• Phenyl dichlorophosphate
• Diethyl phthalate
• Phenyl butyrate
• Benzoin
• Diphenyl chlorophosphate
• Triphenyl phosphate
• Dimethyl phthalate
• Phenylhydrazine
• Tris(trimethylsilyl)phosphate
• PHENYL VALERATE
• PHENYL ACETATE
• Diethylene glycol dibenzoate
• Methyl acrylate
• Emamectin benzoate