Methyl benzoate

Methyl benzoate
Methyl benzoate
Methyl benzoate
3D model of methyl benzoate
3D model of methyl benzoate
Names
Preferred IUPAC name
Methyl benzoate
Systematic IUPAC name
Methyl benzenecarboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.055
UNII
  • InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3 checkY
    Key: QPJVMBTYPHYUOC-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3
    Key: QPJVMBTYPHYUOC-UHFFFAOYAK
  • O=C(OC)c1ccccc1
Properties[3]
C6H5COOCH3
Molar mass 136.150 g·mol−1
Appearance Colourless liquid
Density 1.0837 g/cm3
Melting point −12.35 °C (9.77 °F; 260.80 K)
Boiling point 199 °C (390 °F; 472 K)
log P 2.1[1]
Vapor pressure 0.51 hPa (0.0074 psi)[2]
−81.95×10−6 cm3/mol
1.5164
Viscosity 1.94 mPa·s (23 °C (73 °F; 296 K))[1]
Hazards
GHS labelling:[2]
GHS08: Health hazardGHS07: Exclamation mark
Warning
H227, H302, H361, H402
P201, P202, P210, P264, P270, P273, P280, P301+P312+P330, P308+P313, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
[1]
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 77 °C (171 °F; 350 K)[1]
518 °C (964 °F; 791 K)[1]
Explosive limits 8.6%–20%[1]
Lethal dose or concentration (LD, LC):
1625 mg/kg (rat, male)[2]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5COOCH3, sometimes abbreviated as PhCO2Me, where Ph and Me are phenyl and methyl, respectively. Its structure is C6H5−C(=O)−O−CH3. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents. Methyl benzoate has a pleasant smell, with almond and floral aromas, 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.[4][5]

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.[6] 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.[7]

Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate; drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.[8][9]

Uses

Nonelectric heat cost allocators. See: DIN EN 835.

References

  1. ^ a b c d e f "SDS - Methyl benzoate". www.fishersci.com. ThermoFisher Scientific. 18 December 2025. p. 3. Retrieved 21 April 2026.
  2. ^ a b c Sigma-Aldrich Co., product no. m29908.
  3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton, Florida: CRC Press. pp. 3–360, 3–578. ISBN 9781498754293.
  4. ^ Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 978-3-527-30673-2..
  5. ^ John McMurry (2008). Organic Chemistry (7th ed.). Thompson - Brooks/Cole. p. 623. ISBN 978-1-4390-4972-3.
  6. ^ 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.
  7. ^ 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. S2CID 2845587.
  8. ^ 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. Vol. 2937. p. 19. doi:10.1117/12.266783. S2CID 95964809.
  9. ^ 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. Vol. 2937. p. 216. doi:10.1117/12.266775. S2CID 93295016.
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