Methyl benzoate

Methyl benzoate Chemical Properties
Melting point -12 °C (lit.)
Boiling point 198-199 °C (lit.)
density 1.088 g/mL at 20 °C (lit.)
vapor density 4.68 (vs air)
vapor pressure <1 mm Hg ( 20 °C)
FEMA 2683 | METHYL BENZOATE
refractive index n20/D 1.516(lit.)
Fp 181 °F
storage temp. Store at +5°C to +30°C.
solubility ethanol: soluble60%, clear (1mL/4ml)
form Liquid
color Clear colorless to pale yellow
Specific Gravity1.087~1.095 (20℃)
Odorat 1.00 % in dipropylene glycol. phenolic wintergreen almond floral cananga
Odor Typephenolic
explosive limit8.6-20%(V)
Water Solubility <0.1 g/100 mL at 22.5 ºC
JECFA Number851
Merck 14,6024
BRN 1072099
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases.
LogP2.12-2.2 at 20℃
CAS DataBase Reference93-58-3(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, methyl ester(93-58-3)
EPA Substance Registry SystemMethyl benzoate (93-58-3)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
RIDADR UN 2938
WGK Germany 1
RTECS DH3850000
Autoignition Temperature510 °C
TSCA Yes
HS Code 29163100
Hazardous Substances Data93-58-3(Hazardous Substances Data)
ToxicityLD50 orally in rats: 3.43 g/kg (Smyth)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Methyl benzoate Usage And Synthesis
DescriptionMethyl 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 PropertiesMethyl 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 propertiesMethyl 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.
OccurrenceMethyl 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.
UsesMethyl 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.
ApplicationMethyl 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.
PreparationMethyl 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.
DefinitionChEBI: 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 valuesDetection: 110 ppb
Taste threshold valuesTaste 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 DescriptionA 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 ReactionsSlightly soluble in water. Hydrolyzes slowly in contact with water .
Reactivity ProfileMethyl 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. .
HazardToxic by ingestion.
Health HazardMethyl 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 ProfileModerately 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.
SynthesisMethyl 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 ExposureUsed as food additive and as a solvent for cellulose esters and ethers, resins and rubber.
Purification MethodsWash the ester with dilute aqueous NaHCO3, then water, dry with Na2SO4 and fractionally distil it in a vacuum. [Beilstein 9 IV 283.]
Waste DisposalDissolve 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.
Methanol Paraquat dichloride Sodium benzoate Methyl Acetonitrile Sodium methylparaben Basic Violet 1 ETHYL 3-FLUOROBENZOATE Methyl 2-iodobenzoate Methyl 4-methylbenzoate Kresoxim-methyl Methyl 4-(bromomethyl)benzoate Emamectin benzoate Methyl benzoate Benzoic acid Benzyl benzoate BENZOICACID Methyl benzoylformate

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