ChemicalBook > Product Catalog > Organic Chemistry > Ethers and derivatives > Ethers, ether-alcohols > Anisole
Basic information Product Features Toxicity Limited use Chemical properties Uses Production method Category Toxicity grading Acute toxicity Stimulus data Flammability hazard characteristics Storage feature Extinguishing agents Occupational standards Safety Related Supplier
Anisole Chemical Properties
- Melting point:-37 °C
- Boiling point:154 °C(lit.)
- Density 0.995 g/mL at 25 °C(lit.)
- vapor density 3.7 (vs air)
- vapor pressure 10 mm Hg ( 42.2 °C)
- FEMA 2097 | ANISOLE
- refractive index n
- Flash point:125 °F
- storage temp. Store at RT.
- solubility 1.71g/l
- form Liquid
- color Clear colorless
- Relative polarity0.198
- Odorphenol, anise odor
- Odor Threshold0.057ppm
- explosive limit0.34-6.3%(V)
- Water Solubility 1.6 g/L (20 ºC)
- JECFA Number1241
- Merck 14,669
- BRN 506892
- Stability:Stable. Flammable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference100-66-3(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzene, methoxy-(100-66-3)
- EPA Substance Registry SystemAnisole (100-66-3)
- Hazard Codes Xn,Xi
- Risk Statements 10-38-20-36/37
- Safety Statements 37/39-26-16-24/25
- RIDADR UN 2222 3/PG 3
- WGK Germany 2
- RTECS BZ8050000
- Autoignition Temperature887 °F
- TSCA Yes
- HazardClass 3
- PackingGroup III
- HS Code 29093090
- Hazardous Substances Data100-66-3(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 3700 mg/kg (Taylor)
Anisole Usage And Synthesis
- Product FeaturesAnisole, also known as anise ether, methoxybenzene methyl phenyl ether, is a colorless liquid with an odor of anise, sweet, naturally present in the tarragon oil, insoluble in water, soluble in alcohol, ether, acetone, soluble in benzene. It irritates the eyes and mucous membranes. It is obtained originally from distilled methyl salicylate or methoxybenzoate, is now mainly produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Anisole is prone to start Electrophilic substitution reaction in aromatic nucleus, and condensed with formaldehyde to produce viscous oil or resin material, reacts with phosphorus trichloride to produce chlorine anisole and a small amount of o-chloro product, reacts with thionyl chloride to produce 2,4,6-trichloroanisole. In addition, anisole is heated to react with hydrobromic or hydroiodic, carbon-oxygen bond cleaves, phenol and halogenated methane is produced, which is an important method for determining methoxy group of benzene ring.
The above information is edited by the chemicalbook of Yan Yanyong.
- ToxicityGRAS (FEMA).
LD50 3700 mg/kg (rat, oral).
- Limited useFEMA (mg/kg): Soft drinks 9.0, cold 16, confectionery51, bakery 34.
limited in moderation (FDA§172.515,2000).
- Chemical propertiesIt is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.
- Uses1. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.
2. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.
3. It is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.
4. It is used in organic synthesis, also used as solvents, perfume and insect repellent.
5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.
- Production methodIt is produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Phenol was mixed with sodium hydroxide solution, dimethyl sulfate was slowly added at below 10 ℃. And then heat to 40 ℃, reflux for 18h, then stand for separation of the oil and dried with anhydrous calcium chloride, vacuum distillation to obtain anisole.
It is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react.
It is generated from heating phenol and methanol.
It is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.
- CategoryFlammable liquid
- Toxicity gradingModerate toxicity
- Acute toxicityOral-rat LD50: 3700 mg/kg. Oral-Mouse LD50: 2800 mg/kg
- Stimulus dataSkin-rabbit 500 mg/24 hours moderate
- Flammability hazard characteristicsIn case of fire, high temperature, strong oxidants, it is combustible. Burning discharges irritative smoke.
- Storage featurecomplete package, with care, warehouse ventilation, away from open flame, heat, and stored separately from oxidants
- Extinguishing agentsFoam, carbon dioxide, dry sandy, soil
- Occupational standardsSTEL 10 mg/m3
- Chemical PropertiesClear straw colored liquid
- Chemical PropertiesAnisole is a colorless to yellowish liquid with an agreeable, aromatic, spicy-sweet odor.
- Chemical PropertiesAnisole has a characteristic pleasant, anise-like, agreeable aromatic odor.
- OccurrenceReported found in apple juice and in the oil of Artemisia dracunculus var. turkestanica; also reported found in butter, Camembert cheese, roasted beef, olive (Olea europae), Malay apple, Jerusalem artichoke (Helianthus tuberosus), Bourbon vanilla, truffles, crab and sopadilla fruit (Achras sapota L.).
- UsesA biochemical for proteomics research.
- UsesIn perfumery, in organic syntheses.
- DefinitionChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.
- PreparationBy reacting phenol and dimethyl sulfate in the presence of aqueous NaOH; by passing methyl chloride into a suspension of sodium phenolate in liquid ammonia
- Aroma threshold valuesDetection: 50 ppb
- Synthesis Reference(s)Canadian Journal of Chemistry, 40, p. 441, 1962 DOI: 10.1139/v62-070
Journal of the American Chemical Society, 88, p. 4271, 1966 DOI: 10.1021/ja00970a037
Organic Syntheses, Coll. Vol. 1, p. 58, 1941
- General DescriptionA clear straw-colored liquid with an aromatic odor. Insoluble in water and the same density as water. Vapors heavier than air. Flash point 125°F. Boiling point 307°F. Moderately toxic by ingestion. A skin irritant. Used to make perfumes, flavorings and as a solvent.
- Air & Water ReactionsFlammable. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Insoluble in water
- Reactivity ProfileEthers, such as Anisole can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
- Health HazardInhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
- Safety ProfileModerately toxic by ingestion and inhalation. A skin irritant. A flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid fumes.
- Potential ExposureAnisole is used as a solvent; a flavoring, vermicide, making perfumes; and in organic synthesis.
- ShippingUN2222 Anisole, Hazard Class: 3; Labels: 3- Flammable liquid.
- Purification MethodsShake anisole with half its volume of 2M NaOH, and the emulsion is allowed to separate. Repeat three times, then wash twice with water, dry over CaCl2, filter, dry over sodium wire and finally distil it from fresh sodium under N2 using a Dean-Stark trap (samples in the trap being rejected until free from turbidity) [Caldin et al. J Chem Soc, Faraday Trans 1 72 1856 1976]. Alternatively dry it with CaSO4 or CaCl2, or by refluxing with sodium or BaO with crystalline FeSO4 or by passage through an alumina column. Traces of phenols are removed by prior shaking with 2M NaOH, followed by washing with water. It has been be purified by zone refining. [Beilstein 6 IV 548.]
- IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
- 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.
Anisole Preparation Products And Raw materials
- Raw materialsSodium hydroxideDimethyl sulfatePhenolDimethyl ether
- Preparation Products1-Methyl-1H-imidazole-4-carboxylic acidImidazole-4-methanol4,5-Imidazoledicarboxylic acid1-METHYL-1H-IMIDAZOLE-5-CARBOXYLIC ACIDCefdinir1,5-Diazabicyclo[4.3.0]non-5-ene4,5-DICARBOXY-1-METHYL-1H-IMIDAZOLEALLURA RED ACDiaveridineCeftibutenPYRIDIN-4-YLMETHYL-HYDRAZINEPYRIDIN-2-YLMETHYL-HYDRAZINE1H-Imidazole-4-carboxylic acidMethyldopa1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILEPYRIDIN-3-YLMETHYL-HYDRAZINELawesson's Reagent6-Hydroxy-1-naphthoic acidDisperse Blue BGLBunazosin hydrochlorideCHLOROTRIANISENEcleaner LSCefcapene pivoxilVerapamil6-METHOXY-1-NAPHTHOIC ACIDpoly AO-79Alacepriltrisodium [5-acetamido-4-hydroxy-3-[[2-hydroxy-5-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonato(5-)]cuprate(3-) 2-Bromoanisole3-(4-METHOXYBENZOYL)PROPIONIC ACID1H-Imidazole-4,5-dicarbonitrile4-Chloro-4'-hydroxybenzophenone4-chloro-4'-methoxybenzophenone1-CHLOROMETHYL-2,3,4-TRIMETHOXYBENZENEMETHOXYCHLORAnisyl acetateFast Scarlet Base LG2,4,6-TRIBROMOANISOLEFenofibrate4-Fluoro-4'-methoxybenzophenone
- Phenol Phenetole Veratraldehyde Thiophanate-methyl Methyl acetate Tribenuron methyl m-Anisyl alcohol 3-Bromoanisole 3,4-Dimethoxyphenethylamine (Trifluoromethoxy)benzene 4'-Methoxyacetophenone anisole,p-propenyl Anise oil (3-Methoxyphenyl)acetonitrile Kresoxim-methyl p-Anisaldehyde Methyl salicylate METSULFURON METHYL
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