Phenyl benzoate

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
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).
Infobox references

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]

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

  1. 1 2 3 4 5 6 7 PubChem. "Phenyl benzoate". pubchem.ncbi.nlm.nih.gov. Retrieved 20 March 2026.
  2. 1 2 3 Sigma-Aldrich. "Phenyl benzoate". www.sigmaaldrich.com. Retrieved 20 March 2026.
  3. 1 2 3 4 5 6 Chemical Book. "Phenyl benzoate". amp.chemicalbook.com. Retrieved 20 March 2026.
  4. ↑ ThermoFisher. "Phenyl benzoate, 99%". www.thermofisher.com. Retrieved 20 March 2026.
  5. ↑ Hill, Graham; Holman, John (21 March 2000). "Chemistry in Context". Nelson Thornes. Retrieved 21 March 2026 – via Google Books.
  6. ↑ Lee, Yao-Sheng; Yeh, Mou-Yung; Shih, Yen-Ping (1 May 1995). "Phase-Transfer Catalytic Kinetics of the Synthesis of Phenyl Benzoate". Industrial & Engineering Chemistry Research. 34 (5): 1572–1580. doi:10.1021/ie00044a009. Retrieved 21 March 2026 – via ACS Publications.
  7. ↑ Bogatyreva, I. K.; Avakyan, V. G.; Khodzhaeva, V. L. (1 March 1995). "Spectroscopic and conformational study of phenyl benzoate". Russian Chemical Bulletin. 44 (3): 443–447. doi:10.1007/BF00702384. Retrieved 21 March 2026 – via Springer Link.
  8. ↑ Fukushi, Yukako; Yoshino, Hironori; Ishikawa, Junya; Sagisaka, Masanobu; Kashiwakura, Ikuo; Yoshizawa, Atsushi (12 February 2014). "Synthesis and anticancer properties of phenyl benzoate derivatives possessing a terminal hydroxyl group". Journal of Materials Chemistry B. 2 (10): 1335–1343. doi:10.1039/C3TB21736A. Retrieved 21 March 2026 – via pubs.rsc.org.
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