Methyl benzoate

Methyl benzoate
Names
	IUPAC name Methyl benzoate
Identifiers
CAS Number	93-58-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL16435 ;
ChemSpider	6883 ;
ECHA InfoCard	100.002.055
PubChem CID	7150;
UNII	6618K1VJ9T ;
CompTox Dashboard (EPA)	DTXSID5025572 ;
	InChI InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3 Key: QPJVMBTYPHYUOC-UHFFFAOYSA-N ; InChI=1/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3 Key: QPJVMBTYPHYUOC-UHFFFAOYAK;
	SMILES O=C(OC)c1ccccc1;
Properties
Chemical formula	C8H8O2
Molar mass	136.150 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
NFPA 704 (fire diamond)	0 2 0
Flash point	82 °C (180 °F; 355 K)
Safety data sheet (SDS)	ScienceLab MSDS
Related compounds
Related compounds	Ethyl benzoate; Propyl benzoate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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

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

^ John McMurry (2008). Organic Chemistry, 7th Edition. Thompson - Brooks/Cole. ISBN 1-4390-4972-6.. Page 623
^ 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.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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. {{cite journal}}: |chapter= ignored (help); Cite journal requires |journal= (help)
^ 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. {{cite journal}}: |chapter= ignored (help); Cite journal requires |journal= (help)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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. {{cite journal}}: |chapter= ignored (help); Cite journal requires |journal= (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. {{cite journal}}: |chapter= ignored (help); Cite journal requires |journal= (help)

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