METHYL BENZOATE

CAS No.: 93-58-3
EC No.: 202-259-7

Description    Methyl benzoate is found in allspice. Methyl benzoate is present in various flower oils, banana, cherry, pimento berry, ceriman (Monstera deliciosa), clove bud and stem, mustard, coffee, black tea, dill, starfruit and cherimoya (Annona cherimola). Methyl benzoate is used in flavourings.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 is commonly used as bait to attract and collect these bees for study. Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid. It is a colorless to slightly yellow liquid that is insoluble with water, but miscible with most organic solvents.

Methyl benzoate
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Methyl benzoate
Methyl benzoate in glass bottle.jpeg
3D model of methyl benzoate
Methyl benzoate
Names
Preferred IUPAC name
Methyl benzoate
Systematic IUPAC name
Methyl benzenecarboxylate
Identifiers
CAS Number    
93-58-3 check
3D model (JSmol)    
Interactive image
ChEMBL    
ChEMBL16435 check
ChemSpider    
6883 check
ECHA InfoCard    100.002.055 Edit this at Wikidata
PubChem CID    
7150
UNII    
6618K1VJ9T check
CompTox Dashboard (EPA)    
DTXSID5025572 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    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)
Magnetic susceptibility (χ)    −81.95×10−6 cm3/mol
Refractive index (nD)    1.5164
Hazards
Safety data sheet    ScienceLab MSDS
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
200
Flash point    82 °C (180 °F; 355 K)
Related compounds
Related compounds    
Ethyl benzoate
Propyl benzoate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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.

Contents
1    Synthesis and reactions
2    Occurrence
3    Uses
4    References
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]

Methyl benzoate price More Price(22)
Manufacturer    Product number    Product description    CAS number    Packaging    Price    Updated    Buy
Sigma-Aldrich    18344    Methyl benzoate analytical standard    93-58-3    1ml-f    $20.7    2020-08-18    Buy
Sigma-Aldrich    18344    Methyl benzoate analytical standard    93-58-3    5ml-f    $68.7    2020-08-18    Buy
TCI Chemical    B0074    Methyl Benzoate >99.0%(GC)    93-58-3    25mL    $13    2020-06-24    Buy
TCI Chemical    B0074    Methyl Benzoate >99.0%(GC)    93-58-3    500mL    $26    2020-06-24    Buy
Alfa Aesar    A12404    Methyl benzoate, 99%    93-58-3    250g    $13.9    2020-06-24    Buy
Methyl benzoate Chemical Properties,Uses,Production
Flavors and perfume
Methyl benzoate is a commonly used aromatic carboxylic acid esters, flavors, and fragrances in daily chemical industry of China with strong floral, fruity aroma and ylang and tuberose like nuances as well as phenol breath. It is naturally presented in ylang oil, tuberose oil, clove oil, oil of Kalanchoe and daffodils oil and some other kinds of essential oils.
Methyl benzoate is the food flavors allowed by the provision of the GB2760-1996 of China and can be used for modulation of strawberry, raspberry, cherry, pineapple, rum, vanilla beans and nuts flavor and some other kinds of flavor essence; it can be applied to food and can also be applied to daily flavor formulations for the preparation the base of ylang type and flower flavor type incense with the amount being less than 12%. There is no restriction in IFRA.
Methyl benzoate was identified as GRAS by FEMA with the FEMA number being 2683 and approved by the FDA for human administration. The Council of Europe has listed methyl benzoate into the table of artificial flavor which can be used for food and is harmless to the human health with the maximum amount being 61 mg/kg and ADI being 5 mg/kg.
Methyl benzoate is stable in air and can be slowly oxidized in the presence of an oxidizing agent; it can react with base and can subject to saponification with generating benzonic acid. It can also have transesterification to prepare other kinds of benzoates; it is also susceptible to hydrolysis. According to the information provided by RIFM, the acute toxicity data of methyl benzoate: oral LD50: 3.4g/kg (rats).
The traditional method is based on the esterfication of the benzoate and methanol in the presence of sulfuric acid for generating methyl benzoate. Since the methyl benzoate is the intermediate in the production of polymer material-the by-product of dimethyl terephthalate. Therefore, we can try to isolate and obtain the product which can meet the perfumer specification from the crude methyl benzoate.
Methyl benzoate can not only be used for the preparation of rosette, geranium type and other flavors but also be used as the solvents of cellulose esters, cellulose ether, resins and rubber; it can also be used for the fiber dyeing of hydrophobic polyester and can shorten the dyeing time, reduce the dyeing temperature and improve the degree of wash fastness after dyeing fabric.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Content Analysis
Measure it according to the method 1 in the ester assay (OT-18). The amount of the taken sample is 900 mg. Take 68.08 as the equivalency factors for calculation or measure it according to the non-polar column method according to the gas chromatography (GT-10-4) method.
Toxicity
ADI: 5mg/kg (CE).
LD50: 1350mg/kg (rat, oral).
Limited use
FEMA (mg/kg): Soft drinks 2.2; cold drink 4.5; candy 8.4; Bakery 9.9; Gum: 61.
Take appropriate amount as limit (FDA§172.515, 2000);
Chemical Properties
It is colorless oily liquid with strong floral and cherry aromas. It is miscible with ethyl ether, soluble in methanol, ethyl ether but insoluble in water and glycerol.
Uses
It can be used as the solvents of cellulose esters, cellulose ethers, synthetic resins and rubber as well as the dyeing auxiliary agent of polyester fiber. It can be used for the preparation of flavors.
It can be used as the solvent in the microscopic analysis as well as the solvent for cellulose.
GB 2760-1996 provides it as allowable food flavors. It can be mainly used for the preparation of strawberry, raspberry, pineapple, cherry, vanilla beans, nuts and rum flavor.
It is commonly used spices for formulating ylang, tuberose scent type. It can also be applied to daffodils, lavender, clove and savory type of Spanish leather. Being used in combination with rock rose product, oak moss or tree moss as well as vetiver oil, it can be used for preparing fern type to achieve pleasant scent. IT can be applied to inexpensive detergent, bad-smell masking agents as well as industrial flavor. It can also be widely applied to food flavors such as strawberry type and so on.
For flavor preparation, it is also used as a cellulose ester, cellulose ether solvent, resin, rubber, etc.
It can be used for organic synthesis; for the solvents of cellulose esters, cellulose ether, resin, rubber and so on; it can also be used as spice with rich aroma of wintergreen oil and cananga oil. It can be used for preparation of soap and cosmetics-purpose artificial ylang oil and sesame oil; it can also be used as food flavor for the preparation of strawberry, pineapple, cherries and rum.
Production method
Put through the hydrogen chloride gas into the methanol solution of the benzoic acid.
It can be produced through the reaction of benzoic acid and dimethyl sulfate at elevated temperatures.
It can be produced from the co-heating between benzoic acid and methanol in the presence of sulfuric acid.
Category
Toxic substances.
Toxicity grading
Poisoning
Acute toxicity
Oral-rat-LD50: 1177 mg/kg; Oral-Mouse LD50: 3330 mg/kg.
Skin irritation data
Rabbit 10 mg/24 hr Mild; Eyes-rabbit 500 mg/24 hr mild.
Explosive and hazardous characteristics
High-temperature, explosive.
Combustible property and hazard characteristics
Combustible upon fire.
Storage characteristics
Treasury: ventilation, low-temperature and dry; store and transport it separately from food and oxidant.
Extinguishing Media
Foam, dry powder, carbon dioxide.
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.
Methyl benzoate is used in perfume bases, such as ylang-ylang and tuberose types.
Chemical Properties
Methyl benzoate is a colorless, oily, transparent, liquid. Pleasant odor.
Chemical Properties
colourless to light yellow fragrant liquid
Chemical Properties
Methyl paraben is methyl ester of p-hydroxybenzoic acid. It does not occur naturally and is produced commercially by esterification of p-hydroxybenzoic acid. Methyl benzoate has a fruity odor, also similar to cananga.
Chemical Properties
Methyl benzoate has a fruity odor, similar to cananga.
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 perfumes..
Uses
In perfumes (Peau d'Espagne).
Definition
ChEBI: A benzoate ester obtained by condensation of benzoic acid and methanol.
Preparation
By heating benzoic acid and dimethyl sulfate to high temperature, or by exchange between ethyl benzoate and methanol in KOH solution.
Production Methods
The compound is manufactured by heating methanol and benzoic acid in the presence of sulfuric acid or by passing dry hydrogen chloride through a solution of benzoic acid in methanol . It may also be produced by the alcoholysis of benzonitrile . It is a by-product of ozonolysis of water .
Aroma threshold values
Detection: 110 ppb
Taste threshold values
Taste characteristics at 30 ppm: phenolic and cherry pit with a camphoraceous nuance.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 31, p. 4209, 1983 DOI: 10.1248/cpb.31.4209
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
Irritating to the eyes, nose, throat, upper respiratory tract, and skin. May cause allegic skin and respiratory reactions.
Health Hazard
Methyl benzoate is a mild skin irritant. 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.
Fire Hazard
Special Hazards of Combustion Products: None
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.
Chemical 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.
Methyl benzoate Preparation Products And Raw materials

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 feijoatree, 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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Other names
Methyl benzoate (IUPAC Name); benzoic acid methyl ester; Methyl ester benzoic acid; Methyl benzenecarboxylate; Methylbenzoat; methylbenzoate; o-methyl benzoate

Synonyms:
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EC 202-259-7; SCHEMBL7200; KSC487A6F; MLS001050185; CHEMBL16435; SCHEMBL4790973; DTXSID5025572; SCHEMBL10330498; CTK3I7062; KS-00000VMQ; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; NSC9394; Methyl benzoate, >=99% (GC); ZINC156868; ACT10969; NSC-9394; Methyl benzoate, analytical standard; Tox21_201832; Tox21_303198; ANW-75136; BBL010502; SBB058212; STK021498; AKOS000120640; Methyl benzoate, >=98%, FCC, FG; LS-1945; MCULE-3681534655; UN 2938; C(C1=CC=CC=C1)(=O)O[C]; Methyl benzoate, for synthesis, 98.0%; NCGC00091665-01; NCGC00091665-02; NCGC00256939-01; NCGC00259381-01; SC-18079; SMR001216584; VS-02533; B0074; FT-0622713; ST51015549; Methyl benzoate, natural, >=98%, FCC, FG; C20645; 102027-EP2272817A1; 102027-EP2275469A1; 102027-EP2287940A1; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; 102027-EP2289965A1; 102027-EP2301983A1; 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Methyl benzoate; Metil benzoat; 202-259-7 [EINECS]; 93-58-3 [RN]; Benzoate de méthyle [French] [ACD/IUPAC Name]; Benzoato di metile [Italian]; Benzoesäuremethylester [German]; benzoic acid methyl ester; Benzoic acid, methyl ester [ACD/Index Name]; Methyl benzenecarboxylate; Methyl benzoate [ACD/IUPAC Name]; Methylbenzoaat [Dutch]; Methylbenzoat [German]; Methyl-benzoat [German] [ACD/IUPAC Name]; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; methylbenzoate; Methylester kyseliny benzoove [Czech]; metil benzoato [Portuguese]; MFCD00008421 [MDL number]; 202-284-3 [EINECS]; 204995-53-9 [RN]; 208396-40-1 [RN]; 25764-08-3 [RN]; 442197-98-0 [RN]; 5-22-02-00059 [Beilstein]; 91929-46-3 [RN]; Benzoic acid-methyl ester; Clorius; Clorius (VAN); METHYL BENZOATE-CARBONYL-13C; Methyl Benzoate-d8; methyl_benzoate; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; 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ST51015549; Methyl benzoate, natural, >=98%, FCC, FG; C20645; 102027-EP2272817A1; 102027-EP2275469A1; 102027-EP2287940A1; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; 102027-EP2289965A1; 102027-EP2301983A1; 102027-EP2371831A1; A844641; Methyl benzoate [UN2938] [Keep away from food]; Q417328; J-522592; Methyl benzoate [UN2938] [Keep away from food]; Z19825577; F0001-2239; Benzoic acid, methyl ester; Methyl benzenecarboxylate; Benzoate, methyl ester; Methyl benzenecarboxylic acid; Methyl benzoic acid; Benzoic acid methyl ester; Clorius; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; Methyl ester; benzoic acid; Methylbenzoate; Niobe oil; Oil OF niobe; Oniobe oil; benzoic acid methyl ester; clorius; methyl benzene carboxylate; methyl benzenecarboxylate; o-methyl benzoate; ortho-methyl benzoate; methyl benzoate FCC; methyl benzoate natural; methyl benzoate pure; methylbenzoate; niobe oil; FEMA 2683; NIOBE OIL; Oilofmiobe; Oniobe oil; Oxidate le; OIL OF NIOBE; Methylbenzoat; Slethylbenzoat; METHYL BENZOATE; ESSENCE OF NIOBE; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; 202-259-7 [EINECS]; 93-58-3 [RN]; Benzoate de méthyle [French] [ACD/IUPAC Name]; Benzoato di metile [Italian]; Benzoesäuremethylester [German]; benzoic acid methyl ester; Benzoic acid, methyl ester [ACD/Index Name]; Methyl benzenecarboxylate; Methyl benzoate [ACD/IUPAC Name]; Methylbenzoaat [Dutch]; Methylbenzoat [German]; Methyl-benzoat [German] [ACD/IUPAC Name]; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; methylbenzoate; Methylester kyseliny benzoove [Czech]; metil benzoato [Portuguese]; MFCD00008421 [MDL number]; 202-284-3 [EINECS]; 204995-53-9 [RN]; 208396-40-1 [RN]; 25764-08-3 [RN]; 442197-98-0 [RN]; 5-22-02-00059 [Beilstein]; 91929-46-3 [RN]; Benzoic acid-methyl ester; Clorius; Clorius (VAN); METHYL BENZOATE-CARBONYL-13C; Methyl Benzoate-d8; methyl_benzoate; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat; Niobe oil; Oniobe oil; VS-02533; WLN: 1OVR; methylbenzoate; benzoic acid; methyl ester; clorius; benzoic acid methyl ester, niobe oil; oil of niobe; methyl benzenecarboxylate; essence of niobe; oniobe oil; oxidate le; METHYL BENZOATE; METİL BENZOAT; Methyl benzoate; Metil benzoat