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| Methyl benzoate | |
|---|---|
 |
|
| IUPAC name | Methyl benzoate |
| Identifiers | |
| CAS number | [93-58-3] |
| SMILES |
|
| Properties | |
| Molecular formula | C8H8O2 |
| Molar mass | 136.15 g/mol |
| Density | 1.094 g/cm³ |
| Melting point |
-12.5 °C |
| Boiling point |
199.6 °C |
| Hazards | |
| MSDS | Oxford MSDS |
| NFPA 704 |
 2
0
0
|
| Flash point | 82 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid. It is a colorless to slightly yellow liquid that is insoluble with water, but miscible with most organic solvents.
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, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[1]
Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate;[2] drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.[3]
Reactions
- Electrophilic substitution: Methyl benzoate undergoes nitration with nitric acid in the presence of sulfuric acid, forming methyl 3-nitrobenzoate. This takes place when nitric acid is protonated and forms the NO2+, nitronium cation. This cation is the electrophile and attacks the benzene ring to form methyl 3-nitrobenzoate.
- Saponification: Methyl 3-nitrobenzoate undergoes hydrolysis with addition of aqueous NaOH. The ester is converted into a carboxylic acid. The result is the sodium salt of the acid, which can be acidified with aqueous HCl to form 3-nitrobenzoic acid.
See also
References
- ^ Schiestl, F.P.; Roubik, D.W. (2003). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29: 253–257. doi:.
- ^ Dejarme, Lindy E. (1997). "Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities" 2937: 19. doi:.
- ^ Waggoner, L. Paul (1997). "Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate" 2937: 216. doi:.
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