Methyl benzoate

Methyl benzoate
IUPAC name Methyl benzoate
Identifiers
CAS number	93-58-3 Y
PubChem	7150
ChemSpider	6883 Y
UNII	6618K1VJ9T Y
ChEMBL	CHEMBL16435 Y
Jmol-3D images	Image 1
SMILES O=C(OC)c1ccccc1
InChI InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3 Y Key: QPJVMBTYPHYUOC-UHFFFAOYSA-N Y InChI=1/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3 Key: QPJVMBTYPHYUOC-UHFFFAOYAK
Properties
Molecular formula	C8H8O2
Molar mass	136.15 g mol−1
Density	1.0837 g/cm³
Melting point	-12.5 °C, 261 K, 10 °F
Boiling point	199.6 °C, 473 K, 391 °F
Refractive index (nD)	1.5164
Hazards
MSDS	Oxford MSDS
NFPA 704	2 0 0
Flash point	82 °C
Related compounds
Related compounds	Ethyl benzoate Propyl benzoate
Y benzoate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl benzoate is an ester with the chemical formula C₆H₅COOCH₃. It is formed by the condensation of methanol and benzoic acid, in presence of a strong acid such as hydrochloric acid.^[1] It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents.

Reactions

Methyl benzoate undergoes reactions both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitution, methyl benzoate undergoes nitration with nitric acid in the presence of sulfuric acid to give methyl 3-nitrobenzoate. Methyl benzoate 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.

Odor

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. 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.^[2] Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate;^[3] drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.^[4]

References

1. ^ John McMurry (2008). Organic Chemistry, 7th Edition. Thompson - Brooks/Cole. ISBN 1439049726. . Page 623
2. ^ 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. 
3. ^ Dejarme, Lindy E. (1997). Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities. 2937. pp. 19. doi:10.1117/12.266783. 
4. ^ Waggoner, L. Paul (1997). Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate. 2937. pp. 216. doi:10.1117/12.266775.