93-58-3 Usage
Chemical Description
Methyl benzoate is an ester with the chemical formula C8H8O2, commonly used as a flavoring agent.
Description
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.
Chemical Properties
Methyl Benzoate has been found in essential oils (e.g., ylang-ylang oil). It is a colorless liquid with a strong, dry-fruity, slightly phenolic odor. Methyl benzoate can be converted simply into other benzoates by transesterification. Since methyl benzoate is a fairly large by-product in the manufacture of Terylene, earlier synthetic routes such as those starting from benzoic acid or benzoyl chloride have largely been abandoned.
Physical properties
Methyl benzoate is a colorless, oily, transparent, liquid that has a pleasant fruity odor, similar to cananga. miscible with ether, soluble in methanol and ether, insoluble in water and glycerol. It is used in perfume bases, such as ylang-ylang and tuberose types.
Occurrence
Methyl benzoate can be isolated from the freshwater fern Salvinia molesta. 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. Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate; drug - sniffing dogs are thus trained to detect the smell of methyl benzoate.
Uses
Methyl benzoate is used in perfumery. It also finds use as a solvent. It acts as an intermediate and odor agents. Further, it is used to attract insects such as orchid bees. It is also used for cellulose esters, cellulose ethers, synthetic resin and rubber solvent and polyester fibers to assist in the preparation of flavor.
Application
Methyl benzoate is a volatile aromatic ester compound widely used in perfumery industries. It is naturally occurring in guava, mango, and kiwifruit. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones. It can also be utilized as a precursor for:Selective synthesis of benzaldehyde using supported manganese oxide catalysts.Preparation of benzophenone derivatives by reacting with aryl compounds via Friedel-Crafts acylation.
Preparation
Methyl benzoate is manufactured by heating benzoic acid and dimethyl sulfate to high temperature, or by exchange between ethyl benzoate and methanol in KOH solution. It may also be produced by the alcoholysis of benzonitrile. It is a by-product of ozonolysis of water.
Definition
ChEBI: Methyl benzoate is a benzoate ester obtained by condensation of benzoic acid and methanol. It has a role as a metabolite and an insect attractant. It is a benzoate ester and a methyl ester.
Aroma threshold values
Detection: 110 ppb
Taste threshold values
Taste characteristics at 30 ppm: phenolic and cherry pit with a camphoraceous nuance.
General Description
A crystalline solid or a solid dissolved in a liquid. Denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.
Air & Water Reactions
Slightly soluble in water. Hydrolyzes slowly in contact with water .
Reactivity Profile
Methyl benzoate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Methyl benzoate reacts with strong oxidizing agents and strong bases and hydrolyzes slowly in contact with water. .
Hazard
Toxic by ingestion.
Health Hazard
Methyl benzoate is a mild skin irritant. Irritating to the eyes, nose, throat, upper respiratory tract, and skin. May cause allegic skin and respiratory reactions.Theacute oral toxicity in test animals was oflow order. The toxic symptoms in animalsfrom oral administration of this compoundwere tremor, excitement, and somnolence.The LD50 value varies with species. The oralLD50 values in mice and rats are 3330 and1350 mg/kg, respectively.
Safety Profile
Moderately toxic by
ingestion. Mildly toxic by skin contact. A
skin and eye irritant. Combustible liquid
when exposed to heat or flame; can react
with oxidizing materials. To fight fire, use
foam, CO2, dry chemical, water to blanket
fire. When heated to decomposition it emits
acrid smoke and irritating fumes.
Synthesis
Methyl benzoate is formed by the condensation of methanol and benzoic acid, in presence of a strong acid such as hydrochloric acid . It reacts both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitution, methyl benzoate undergoes acidcatalysed nitration with nitric acid to give methyl 3-nitrobenzoate. It 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.
Potential Exposure
Used as food additive and as a solvent
for cellulose esters and ethers, resins and rubber.
Purification Methods
Wash the ester with dilute aqueous NaHCO3, then water, dry with Na2SO4 and fractionally distil it in a vacuum. [Beilstein 9 IV 283.]
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed.
Check Digit Verification of cas no
The CAS Registry Mumber 93-58-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 93-58:
(4*9)+(3*3)+(2*5)+(1*8)=63
63 % 10 = 3
So 93-58-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3
93-58-3Relevant articles and documents
Aerobic oxidative cleavage and esterification of C[dbnd]C bonds catalyzed by iron-based nanocatalyst
An, Yue,Fu, Weiru,Tan, Shangzhi,Wang, Lianyue,Yu, Xiangzhu,Zhao, Zhengjia,Zhu, Lina
, (2022/02/03)
Functionalization of C[dbnd]C bonds by oxidative cleavage plays an important role in organic synthesis. However, the traditional functionalized products are mainly aldehydes, ketones and carboxylic acids, and the substrates are limited to examples of active aromatic olefins with very scarce inactive olefins. Herein we disclose an efficient protocol for the direct formation of esters by oxidative cleavage of C[dbnd]C bonds using heterogeneous iron nanocomposite catalyst supported on nitrogen-doped carbon materials with molecular oxygen and tert-butylhydroperoxide (TBHP) as the oxidants. The results show that molecular oxygen as the terminal oxidant is mainly responsible for the cleavage process, and that the auxiliary oxidant TBHP promotes the formation of the intermediate epoxide, thus increasing the selectivity of the product. The catalytic system has a wide range of substrate compatibility involving the challenging inactive aliphatic and long-chain alkyl aryl olefins. The catalyst was reused seven times with no loss in catalytic activity. Characterization and control experiments uncover that the core-shell Fe and Fe3C nanoparticles encapsulated by graphitic carbon play a predominant role in catalyzing the oxidative cleavage of olefins to esters. Preliminary mechanistic studies disclose that this process involves both free radical reactions and tandem sequential reactions.
Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis
Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.
supporting information, (2022/02/21)
Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
