Chemistry:Phenyl benzoate
| Phenyl benzoate molecule | |
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| IUPAC name
Phenyl benzoate[1]
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C 6H 5COOC 6H 5 | |
| 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] |
Refractive index (nD)
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1.5954 (estimate)[3] |
| Hazards[1] | |
| Main hazards | May cause irritation of the skin and serious irritation of the eyes[4] |
| GHS pictograms | 
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| GHS Signal word | Warning |
| HH302Script error: No such module "Preview warning".Category:GHS errors, HH315Script error: No such module "Preview warning".Category:GHS errors, HH317Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors | |
| PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP270Script error: No such module "Preview warning".Category:GHS errors, PP272Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP301+P317Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP330Script error: No such module "Preview warning".Category:GHS errors, PP333+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1225 mg/kg (mouse, oral) |
| Related compounds | |
Related compounds
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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 C
6H
5COOC
6H
5, 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]
- C
6H
5COCl + C
6H
5OHC
6H
5COOC
6H
5 + 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
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 PubChem. "Phenyl benzoate". https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl-benzoate.
- ↑ 2.0 2.1 2.2 Sigma-Aldrich. "Phenyl benzoate". https://www.sigmaaldrich.com/GB/en/sds/aldrich/142719.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 Chemical Book. "Phenyl benzoate". https://amp.chemicalbook.com/ChemicalProductProperty_EN_CB8256450.htm.
- ↑ ThermoFisher. "Phenyl benzoate, 99%". https://www.thermofisher.com/order/catalog/product/162061000.
- ↑ Hill, Graham; Holman, John (21 March 2000). "Chemistry in Context". Nelson Thornes. https://books.google.com.br/books?id=90IqK540a9AC&pg=PA111&dq=phenyl+benzoate&hl=en&sa=X&ved=0ahUKEwjh5-LCiInhAhVME7kGHQXRALQQ6AEIOjAD#v=onepage&q&f=false. Retrieved 21 March 2026.
- ↑ 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. https://doi.org/10.1021/ie00044a009. Retrieved 21 March 2026.
- ↑ 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. https://doi.org/10.1007/BF00702384. Retrieved 21 March 2026.
- ↑ 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. https://pubs.rsc.org/en/content/articlelanding/2014/tb/c3tb21736a. Retrieved 21 March 2026.
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