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Methyl benzoate

From Wikipedia, the free encyclopedia

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 Edit this at Wikidata
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
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)
−81.95×10−6 cm3/mol
1.5164
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 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
0
2
0
Flash point 82 °C (180 °F; 355 K)
Safety data sheet (SDS) ScienceLab MSDS
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 ?)

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, 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.

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Transcription

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

  1. ^ Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 978-3527306732..
  2. ^ John McMurry (2008). Organic Chemistry (7th ed.). Thompson - Brooks/Cole. p. 623. ISBN 978-1-4390-4972-3.
  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. S2CID 2845587.
  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. Vol. 2937. p. 19. doi:10.1117/12.266783. S2CID 95964809.
  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. Vol. 2937. p. 216. doi:10.1117/12.266775. S2CID 93295016.
This page was last edited on 29 February 2024, at 16:12
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