Methyl benzoate | |
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Methyl benzoate |
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Identifiers | |
CAS number | 93-58-3 |
PubChem | 7150 |
ChemSpider | 6883 |
UNII | 6618K1VJ9T |
ChEMBL | CHEMBL16435 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C8H8O2 |
Molar mass | 136.15 g mol−1 |
Density | 1.0837 g/cm³ |
Melting point |
-12.5 °C, 261 K, 10 °F |
Boiling point |
199.6 °C, 473 K, 391 °F |
Refractive index (nD) | 1.5164 |
Hazards | |
MSDS | Oxford MSDS |
NFPA 704 |
2
0
0
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Flash point | 82 °C |
Related compounds | |
Related compounds | Ethyl benzoate Propyl benzoate |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid, in presence of a strong acid such as hydrochloric acid.[1] It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents.
Methyl benzoate undergoes reactions both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitution, methyl benzoate undergoes nitration with nitric acid in the presence of sulfuric acid to give methyl 3-nitrobenzoate. Methyl benzoate also undergoes hydrolysis with addition of aqueous NaOH to give methanol and sodium benzoate, which can be acidified with aqueous HCl to form benzoic acid.
Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoa tree, and it is used in perfumery. It also finds use as a solvent and as a pesticide used to attract insects. It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[2] Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate;[3] drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.[4]