Methyl benzoate

Methyl benzoate
Names
IUPAC name
Methyl benzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.055
UNII
Properties
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)
−81.95×10−6 cm3/mol
1.5164
Hazards
Safety data sheet 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 fuelHealth code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chlorideReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
2
0
0
Flash point 82 °C (180 °F; 355 K)
Related compounds
Related compounds
Except where otherwise noted, 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

Methyl benzoate is formed by the condensation of methanol and benzoic acid, in presence of a strong acid.[1]

Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate. Nucleophiles attack the carbonyl center, illustrated by hydrolysis with addition of aqueous NaOH to give methanol and sodium benzoate.

Occurrence

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

  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: 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: 216. doi:10.1117/12.266775. |chapter= ignored (help)
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