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Phenyl benzoate

Chemical compound From Wikipedia, the free encyclopedia

Phenyl benzoate is an organic compound with the chemical formula C6H5COOC6H5, often abbreviated as PhCOOPh, where Ph stands for phenyl. It is a white crystalline solid, with odor of geranium. It is the phenyl ester of benzoic acid. It can be obtained by the formal condensation of phenol with benzoic acid.[1]

Quick facts Names, Identifiers ...
Phenyl benzoate
Phenyl benzoate molecule
Names
IUPAC name
Phenyl benzoate[1]
Other names
  • Benzoic acid phenyl ester[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.086 Edit this at Wikidata
EC Number
  • 202-293-2
UNII
  • InChI=1S/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H
    Key: FCJSHPDYVMKCHI-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(=O)OC2=CC=CC=C2
Properties
C6H5COOC6H5
Molar mass 198.221 g·mol−1
Appearance White crystalline solid[1][2]
Odor Geranium[1][3]
Density 1.235 g/cm3[3]
Melting point 68–70 °C (154–158 °F; 341–343 K)[2]
Boiling point 298–299 °C (568–570 °F; 571–572 K)[2]
Insoluble[3]
Solubility Soluble in ethanol, diethyl ether and chloroform.[3]
1.5954 (estimate)[3]
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
 May cause irritation of the skin and serious irritation of the eyes[4]
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H317, H319
P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P501
Lethal dose or concentration (LD, LC):
1225 mg/kg (mouse, oral)
Related compounds
Related compounds
 Benzyl benzoate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Phenyl benzoate can be synthesized in good yield by the reaction between benzoyl chloride and phenol in basic conditions, for example using sodium hydroxide as a catalyst.[5]

C6H5COCl + C6H5OHNaOH→C6H5COOC6H5 + HCl

It can be sinthesized by the reaction of the same reactants, but using quaternary ammonium salts or tertiary amines as catalysts, using polar organic solvents such as dichloromethane and chlorobenzene. Using nonpolar organic solvents, such as n-hexane, benzene and toluene, causes the reaction rate to become slower overall. The order of catalytic activity for various quaternary ammonium salts as catalysts is benzyltributylammonium bromide > tetrabutylammonium hydrogensulfate > tetrabutylammonium bromide > benzyltriethylammonium chloride. The order of catalytic activity for various tertiary amines as catalysts is alkyldimethylamine > triethylamine > tributylamine > trimethylamine. The order of effectiveness of organic solvents is dichloromethane > n-hexane > chlorobenzene > toluene.[6]

Structure

Relative orientation of the benzene rings in phenyl benzoate's molecule varies with phase state and temperature.[7]

Uses

Phenyl benzoate is used in cosmetics as a preservative.[1] It is a key reagent in the synthesis of soluble polyimides using dianhydride and diamine derivatives.[3] Some phenyl benzoate derivatives possessing a terminal hydroxyl group shows anticancer behavior.[8]

References

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