Methyl benzoate
IUPAC name	Methyl benzoate
Identifiers
CAS number	[93-58-3]
SMILES	O=C(OC)C1=CC=CC=C1
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

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

• Ethyl benzoate

References

1. ^ Schiestl, F.P.; Roubik, D.W. (2003). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29: 253–257. doi:10.1023/A:1021932131526. 
2. ^ Dejarme, Lindy E. (1997). "Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities" 2937: 19. doi:10.1117/12.266783. 
3. ^ Waggoner, L. Paul (1997). "Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate" 2937: 216. doi:10.1117/12.266775. 

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