Methyl benzoate

Methyl benzoate
3D model of methyl benzoate	Methyl benzoate
Names
	Preferred IUPAC name Methyl benzoate
	Systematic IUPAC name Methyl benzenecarboxylate
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)
Magnetic susceptibility (χ)	−81.95×10−6 cm3/mol
Refractive index (nD)	1.5164
Hazards
Safety data sheet	ScienceLab MSDS
NFPA 704 (fire diamond)	2 0 0
Flash point	82 °C (180 °F; 355 K)
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).
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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] [2]

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.[3] 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.[4]

Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate;[5] drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.[6]

Uses

Non electric Heat cost allocators. See: DIN EN 835.

References

Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555..
John McMurry (2008). Organic Chemistry, 7th Edition. Thompson - Brooks/Cole. ISBN 978-1-4390-4972-3.. 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. hdl:20.500.11850/57276. PMID 12647866.
Dejarme, Lindy E.; Gooding, Rachel E.; Lawhon, Sara J.; Ray, Prasenjit; Kuhlman, Michael R. (1997). "Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities". In Works, George; Rudin, Leonid I; Hicks, John; et al. (eds.). Proceedings of SPIE. SPIE Proceedings. 2937. p. 19. doi:10.1117/12.266783.
Waggoner, L. Paul; Johnston, James M.; Williams, Marc; Jackson, Jan; Jones, Meredith H.; Boussom, Teresa; Petrousky, James A. (1997). "Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate". In Works, George; Rudin, Leonid I; Hicks, John; et al. (eds.). Proceedings of SPIE. SPIE Proceedings. 2937. p. 216. doi:10.1117/12.266775.

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[Ullmann-1] Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555..

[2] John McMurry (2008). Organic Chemistry, 7th Edition. Thompson - Brooks/Cole. ISBN 978-1-4390-4972-3.. Page 623

[3] 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.

[4] 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. hdl:20.500.11850/57276. PMID 12647866.

[5] Dejarme, Lindy E.; Gooding, Rachel E.; Lawhon, Sara J.; Ray, Prasenjit; Kuhlman, Michael R. (1997). "Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities". In Works, George; Rudin, Leonid I; Hicks, John; et al. (eds.). Proceedings of SPIE. SPIE Proceedings. 2937. p. 19. doi:10.1117/12.266783.

[6] Waggoner, L. Paul; Johnston, James M.; Williams, Marc; Jackson, Jan; Jones, Meredith H.; Boussom, Teresa; Petrousky, James A. (1997). "Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate". In Works, George; Rudin, Leonid I; Hicks, John; et al. (eds.). Proceedings of SPIE. SPIE Proceedings. 2937. p. 216. doi:10.1117/12.266775.