Methyl benzoate

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Methyl benzoate
Methyl benzoate
3D model of methyl benzoate
Identifiers
CAS number 93-58-3 YesY
PubChem 7150
ChemSpider 6883 YesY
UNII 6618K1VJ9T YesY
ChEMBL CHEMBL16435 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O2
Molar mass 136.15 g mol−1
Density 1.0837 g/cm³
Melting point −12.5 °C (9.5 °F; 260.6 K)
Boiling point 199.6 °C (391.3 °F; 472.8 K)
Refractive index (nD) 1.5164
Hazards
MSDS ScienceLab MSDS
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 82 °C (180 °F; 355 K)
Related compounds
Related compounds Ethyl benzoate
Propyl benzoate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5CO2CH3. It is a colorless liquid that is poorly soluble in water, but miscible with 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 such as orchid bees.

Synthesis and reactions[edit]

Methylbenzoate is formed by the condensation of methanol and benzoic acid, in presence of a strong acid such as hydrochloric acid.[1] It reacts both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitution, methyl benzoate undergoes acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate. It 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.

Occurrence[edit]

Methyl benzoate can be isolated from the freshwater fern Salvinia molesta.[2] 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.[3]

Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate;[4] drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.[5]

References[edit]

  1. ^ John McMurry (2008). Organic Chemistry, 7th Edition. Thompson - Brooks/Cole. ISBN 1-4390-4972-6. . Page 623
  2. ^ Choudhary, MI; Naheed, N; Abbaskhan, A; Musharraf, SG; Siddiqui, H; Atta-Ur-Rahman (2008). "Phenolic and other constituents of fresh water fern Salvinia molesta". Phytochemistry 69 (4): 1018–23. doi:10.1016/j.phytochem.2007.10.028. PMID 18177906. 
  3. ^ Schiestl, F.P.; Roubik, D.W. (2003). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866. 
  4. ^ Dejarme, Lindy E.; Gooding, Rachel E.; Lawhon, Sara J.; Ray, Prasenjit; Kuhlman, Michael R. (1997). Works, George; Rudin, Leonid I; Hicks, John et al., eds. "Proceedings of SPIE". SPIE Proceedings 2937. p. 19. doi:10.1117/12.266783.  |chapter= ignored (help)
  5. ^ Waggoner, L. Paul; Johnston, James M.; Williams, Marc; Jackson, Jan; Jones, Meredith H.; Boussom, Teresa; Petrousky, James A. (1997). Works, George; Rudin, Leonid I; Hicks, John et al., eds. "Proceedings of SPIE". SPIE Proceedings 2937. p. 216. doi:10.1117/12.266775.  |chapter= ignored (help)