Methyl benzoate
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2008-05-28T08:05:40Z
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{{Chembox new
| Name = Methyl benzoate
| ImageFile = Methyl benzoate.png
<!-- | ImageSize = 150px -->
| ImageName = Methyl benzoate
| IUPACName = Methyl benzoate
| Section1 = {{Chembox Identifiers
| CASNo = 93-58-3
| SMILES = O=C(OC)C1=CC=CC=C1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>2</sub>
| MolarMass = 136.15 g/mol
| Density = 1.094 g/cm³
| MeltingPt = -12.5 °C
| BoilingPt = 199.6 °C}}
| Section7 = {{Chembox Hazards
| NFPA-H = 0
| NFPA-F = 2
| NFPA-R = 0
| FlashPt = 82 °C
}}
}}
'''Methyl benzoate''' is an [[ester]] with the [[chemical formula]] C<sub>6</sub>H<sub>5</sub>COOCH<sub>3</sub>. 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 bee]]s, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.<ref>{{cite journal | author = Schiestl, F.P.; Roubik, D.W. | year = 2003 | title = Odor Compound Detection in Male Euglossine Bees | journal = [[Journal of Chemical Ecology]] | volume = 29 | pages = 253–257 | doi = 10.1023/A:1021932131526}}</ref>
==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 NO<sub>2</sub><sup>+</sup>, [[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 [[Hydrochloric acid|HCl]] to form [[3-Nitrobenzoic acid|3-nitrobenzoic acid]].
==See also==
*[[Ethyl benzoate]]
==References==
<references/>
[[Category:flavors]]
[[Category:Benzoates]]
[[Category:Carboxylate esters]]
[[Category:Aromatic compounds]]
{{aromatic-stub}}
[[cs:Metylbenzoát]]
[[de:Methylbenzoat]]
[[it:Benzoato di metile]]
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[[pt:Metil benzoato]]
[[ja:安息香酸メチル]]