Methyl benzoate: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 411162742

| Name = Methyl benzoate

| ImageFile2 =Methyl_benzoate_in_glass_bottle.jpeg

| ImageSize2 = 75px

| ImageFileL1 = Methyl benzoate.svg

| ImageSizeL1 = 150px

| ImageNameL1 = Methyl benzoate

| ImageFileR1 = Methyl Benzoate 3D Computer Model.png

| ImageSizeR1 = 150px

| ImageNameR1 = 3D model of methyl benzoate

| PIN = Methyl benzoate

| SystematicName = Methyl benzenecarboxylate

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| CASNo_Ref = {{cascite|correct|CAS}}

| SMILES = O=C(OC)c1ccccc1

}}

|Section2={{Chembox Properties

| C=8 | H=8 | O=2

| Density = 1.0837 g/cm³

| RefractIndex = 1.5164

| MeltingPtC = −12.5

| BoilingPtC = 199.6

| MagSus = −81.95×10⁻⁶ cm³/mol

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.sciencelab.com/msds.php?msdsId=9927228 ScienceLab MSDS]

| NFPA-H = 0

| NFPA-F = 2

| NFPA-R = 0

| FlashPtC = 82

}}

|Section8={{Chembox Related

| OtherCompounds = {{ubl|[[Ethyl benzoate]]|[[Propyl benzoate]]}}

'''Methyl benzoate''' is an [[organic compound]]. It is an [[ester]] with the [[chemical formula]] {{chem2|C6H5COOCH3}}, sometimes abbreviated as {{chem2|PhCO2Me}}, where Ph and Me are [[phenyl]] and [[methyl]], respectively. Its structure is {{chem2|C6H5\sC(\dO)\sO\sCH3}}. 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.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a03_555|title=Benzoic Acid and Derivatives|last1=Maki|first1=Takao|last2=Takeda|first2=Kazuo}}.</ref><ref>{{cite book |title=Organic Chemistry|edition=7th|publisher =Thompson - Brooks/Cole|author = John McMurry|year =2008 |isbn=978-1-4390-4972-3|page=623}}</ref>

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]]''.<ref>{{Cite journal|pmid=18177906|year=2008|last1=Choudhary|first1=MI|last2=Naheed|first2=N|last3=Abbaskhan|first3=A|last4=Musharraf|first4=SG|last5=Siddiqui|first5=H|title=Phenolic and other constituents of fresh water fern Salvinia molesta|volume=69|issue=4|pages=1018–23|doi=10.1016/j.phytochem.2007.10.028|journal=Phytochemistry|last6=Atta-Ur-Rahman}}</ref> It is one of many compounds that is attractive to males of various species of [[orchid bee]]s, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.<ref>{{cite journal |author1=Schiestl, F.P. |author2=Roubik, D.W. | year = 2003 | title = Odor Compound Detection in Male Euglossine Bees | journal = [[Journal of Chemical Ecology]] | volume = 29 | pages = 253–257 | doi = 10.1023/A:1021932131526 | pmid=12647866 | issue = 1| hdl = 20.500.11850/57276 |s2cid=2845587 | hdl-access = free }}</ref>

[[Cocaine]] [[hydrochloride]] hydrolyzes in moist air to give methyl benzoate;<ref>{{cite book | doi = 10.1117/12.266783 | title = Proceedings of SPIE | year = 1997 | author = Dejarme, Lindy E. | volume = 2937 | pages = 19 | chapter = Formation of methyl benzoate from cocaine hydrochloride under different temperatures and humidities | series = SPIE Proceedings | editor1-last = Works | editor1-first = George | editor2-last = Rudin | editor2-first = Leonid I | editor3-last = Hicks | editor3-first = John |display-editors = 3 | editor4-last = Carapezza | editor4-first = Edward M | last2 = Gooding | first2 = Rachel E. | last3 = Lawhon | first3 = Sara J. | last4 = Ray | first4 = Prasenjit | last5 = Kuhlman | first5 = Michael R.| s2cid = 95964809 }}</ref> [[drug-sniffing dog]]s are thus trained to detect the smell of methyl benzoate.<ref>{{cite book | doi = 10.1117/12.266775 | title = Proceedings of SPIE | year = 1997 | author = Waggoner, L. Paul | volume = 2937 | pages = 216 | chapter = Canine olfactory sensitivity to cocaine hydrochloride and methyl benzoate | series = SPIE Proceedings | editor1-last = Works | editor1-first = George | editor2-last = Rudin | editor2-first = Leonid I | editor3-last = Hicks | editor3-first = John |display-editors = 3 | editor4-last = Carapezza | editor4-first = Edward M | last2 = Johnston | first2 = James M. | last3 = Williams | first3 = Marc | last4 = Jackson | first4 = Jan | last5 = Jones | first5 = Meredith H. | last6 = Boussom | first6 = Teresa | last7 = Petrousky | first7 = James A.| s2cid = 93295016 }}</ref>

== Uses ==

Non electric [[Heat cost allocator]]s. See: DIN EN 835.

== References ==

<references />

{{Esters}}

[[Category:Benzoate esters]]

[[Category:Perfume ingredients]]