Methyl benzoate

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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
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 disclaimer and 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.

However drug searching dogs are trained to detect the smell of methyl benzoate because of its connection to cocaine. Cocaine hydrochloride, though in its purest form odorless, naturally decomposes the benzoyl group on the cocaine molecule from the remnants of chemicals used in processing it, producing methyl alcohol and benzole acid, which stabilizes after a short time into methyl benzoate.

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]

[edit] 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.

[edit] See also

Ethyl benzoate

[edit] References

^ 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.