Anisole, 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.
LD50 3700 mg/kg (rat, oral).
Anisole has acute toxicity, LD50: 3700mg/kg (oral in rats); 2800mg/kg (oral in mice). Rabbit percutaneous: 500mg (24h), moderate stimulation. Anisole is also mutagenic, causing DNA inhibition, 25 μmol/L in human lymphocytes.
FEMA (mg/kg): Soft drinks 9.0, cold 16, confectionery51, bakery 34.
limited in moderation (FDA§172.515,2000).
It is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.
1. 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.
It 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.
Oral-rat LD50: 3700 mg/kg. Oral-Mouse LD50: 2800 mg/kg
Skin-rabbit 500 mg/24 hours moderate
Flammability hazard characteristics
In case of fire, high temperature, strong oxidants, it is combustible. Burning discharges irritative smoke.
complete package, with care, warehouse ventilation, away from open flame, heat, and stored separately from oxidants
Foam, carbon dioxide, dry sandy, soil
STEL 10 mg/m3
Clear straw colored liquid
Anisole is a colorless to yellowish liquid with
an agreeable, aromatic, spicy-sweet odor.
Anisole has a characteristic pleasant, anise-like, agreeable aromatic odor.Anisole is used in perfumery.
Reported 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.).
A biochemical for proteomics research.
In perfumery, in organic syntheses.
Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.
Anisole is an organic compound with the chemical formula C7H8O with a pleasant anise-like aroma, used in organic synthesis and also as a solvent, fragrance and insect repellent. For organic synthesis, it is also used as solvent, fragrance and insect repellent.
By reacting phenol and dimethyl sulfate in the presence of aqueous NaOH; by passing methyl chloride into a suspension
of sodium phenolate in liquid ammonia
ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.
Aroma threshold values
Detection: 50 ppb
Canadian Journal of Chemistry, 40, p. 441, 1962 DOI: 10.1139/v62-070Journal of the American Chemical Society, 88, p. 4271, 1966 DOI: 10.1021/ja00970a037Organic Syntheses, Coll. Vol. 1, p. 58, 1941
A 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 Reactions
Flammable. 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
Ethers, 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.
Inhalation 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.
Moderately 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.
Anisole is used as a solvent; a flavoring,
vermicide, making perfumes; and in organic synthesis.
UN2222 Anisole, Hazard Class: 3; Labels: 3-
Shake 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.]
Incompatible 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.
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