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EC / List no.: 202-876-1
CAS no.: 100-66-3
Mol. formula: C7H8O
Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5.
Anisole is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances.
The compound is mainly made synthetically and is a precursor to other synthetic compounds.
Anisole is an ether.
Anisole is a standard reagent of both practical and pedagogical value.
Anisolecan be prepared by the Williamson ether synthesis; sodium phenoxide is reacted with a methyl halide to yield anisole.
Reactivity
Anisole undergoes electrophilic aromatic substitution reaction at a faster speed than benzene, which in turn reacts more quickly than nitrobenzene.
The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites.
The enhanced nucleophilicity of anisole vs. benzene reflects the influence of the methoxy group, which renders the ring more electron-rich.
The methoxy group strongly affects the pi cloud of the ring as a mesomeric electron donor, more so than as an inductive electron withdrawing group despite the electronegativity of the oxygen.
Stated more quantitatively, the Hammett constant for para-substitution of anisole is -0.27.
Illustrative of its nucleophilicity, anisole reacts with acetic anhydride to give 4-methoxyacetophenone:
CH3OC6H5 + (CH3CO)2O → CH3OC6H4C(O)CH3 + CH3CO2H
Unlike most acetophenones, but reflecting the influence of the methoxy group, methoxyacetophenone undergoes a second acetylation.
Many related reactions have been demonstrated.
For example, P4S10 converts anisole to Lawesson's reagent, [(CH3OC6H4)PS2]2.
Also indicating an electron-rich ring, anisole readily forms π-complexes with metal carbonyls, e.g. Cr(η6-anisole)(CO)3.
The ether linkage is highly stable, but the methyl group can be removed with hydroiodic acid:
CH3OC6H5 + HI → HOC6H5 + CH3I
Birch reduction of anisole gives 1-methoxycyclohexa-1,4-diene.
Preparation:
Anisole is prepared by methylation of sodium phenoxide with dimethyl sulfate or methyl chloride:
2 C6H5O−Na+ + (CH3O)2SO2 → 2 C6H5OCH3 + Na2SO4
Applications:
Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals.
For example, synthetic anethole is prepared from anisole.
Anisole appears as a clear straw-colored liquid with an aromatic odor.
Insoluble in water and the same density as water.
Vapors heavier than air.
Moderately toxic by ingestion.
A skin irritant. Used to make perfumes, flavorings and as a solvent.
Use and Manufacturing
IN PERFUMERY; IN ORGANIC SYNTHESES
Important intermediate in the manufacture of organic compounds, for example fragrances and pharmaceuticals.
Anisole is also used as a solvent and heat transfer medium.
Industry Uses
Photosensitive chemicals
Solvents (which become part of product formulation or mixture)
Industry Processing Sectors
Computer and electronic product manufacturing
Photographic film paper, plate, and chemical manufacturing
Anisole is a starting raw material to be chemically transformed by Pharmaceuticals Industries (technical grade). Its appearance is a clear liquid.
Anisole presents a wide range of applications: solvent for chemical reactions, synthesis intermediates and solvent for electronics.
anisole is a colorless liquid ether C6H5OCH3 of pleasant odor obtained by distilling anisic acid or by the action of dimethyl sulfate and alkali on phenol and used chiefly in perfumery; methyl phenyl ether
Product Features
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.
Anisole irritates the eyes and mucous membranes.
Anisole 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.
Chemical properties
Anisole is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.
Uses:
1. GB2760-1996 stipulates it as allowable usable spices in food.
Anisole is mainly used for the preparation of vanilla, fennel and beer flavor.
2. Anisole is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.
3. Anisole is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.
4. Anisole is used in organic synthesis, also used as solvents, perfume and insect repellent.
5. Anisole is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.
Production method
Anisole 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.
Anisole is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react.
Anisole is generated from heating phenol and methanol.
Anisole is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.
Chemical Properties
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.
Occurrence
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.).
Uses:
A biochemical for proteomics research.
In perfumery, in organic syntheses.
Definition
ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.
Preparation
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
General Description
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
Reactivity Profile
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.
Purification Methods
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).
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.
Anisolehas been be purified by zone refining.
About this substance
Helpful information
This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
This substance is used in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using this substance. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing
This substance is used in the following products: laboratory chemicals.
Release to the environment of this substance can occur from industrial use: formulation of mixtures.
Uses at industrial sites
This substance is used in the following products: coating products, laboratory chemicals, pharmaceuticals and semiconductors.
This substance has an industrial use resulting in manufacture of another substance (use of intermediates).
This substance is used in the following areas: scientific research and development.
This substance is used for the manufacture of: chemicals, machinery and vehicles and furniture.
Release to the environment of this substance can occur from industrial use: in processing aids at industrial sites and as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of this substance can occur from industrial use: manufacturing of the substance.
General Description
A clear straw-colored liquid with an aromatic odor.
Insoluble in water and the same density as water. Vapors heavier than air.
Moderately toxic by ingestion.
A skin irritant. Used to make perfumes, flavorings and as a solvent.
Anisole is a colourless pleasant-smelling liquid used as a solvent and vermicide and in perfume and flavouring.
Formula: C6H5OCH3; relative density: 0.996; melting pt: –37.5°C; boiling pt: 155°C
Anisole, also known as methoxybenzene, is a colorless liquid with a smell similar to that of anise seed, and can be quite naseauting.
Anisole is more electron rich than benzene because of the resonance effect of the methoxy group upon the aromatic ring.
This resonance effect has a greater effect upon the pi cloud of the ring than the inductive effect where the electronegative oxygen exerts a pull on the electron density in the benzene ring through the sigma bond.
Anisole reacts with electrophiles in the electrophilic aromatic substitution reaction more quickly than benzene, which in turn reacts more quickly than nitrobenzene.
Rate of reaction:
Anisole > Benzene > Nitrobenzene
The methoxy group acts as an ortho/para directing group.
Anisole is used in perfumery and chemical syntheses, and is an insect pheromone.
Anisole is a flavouring agent Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals.
For example, synthetic anethole is prepared from anisole.
Anisole undergoes electrophilic aromatic substitution reaction more quickly than does benzene, which in turn reacts more quickly than nitrobenzene.
The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites.
The enhanced nucleophilicity of anisole vs benzene reflects the influence of the methoxy group, which renders the ring more electron-rich.
The methoxy group strongly affects the pi cloud of the ring, moreso than the inductive effect of the electronegative oxygen.
belongs to the class of organic compounds known as anisoles.
These are organic compounds containing a methoxybenzene or a derivative thereof.
Anisole or methoxybenzene, is an organic compound with the formula CH3OC6H5.
It is used as a precursor in the production of perfumes and other pharmaceuticals.
Properties
Chemical
Anisole undergoes electrophilic aromatic substitution reaction more quickly than does benzene, which in turn reacts more quickly than nitrobenzene.
The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites.
Physical
Anisole is a colorless or straw-colored liquid, with an odor reminiscent of anise, almost insoluble in water, but soluble in other organic solvents, like acetone or alcohols.
Availability
Anisole is sold by chemical suppliers, and can be bought online.
Preparation
Anisole is best prepared via the Williamson ether synthesis, by reacting sodium phenoxide with methyl iodide.
C6H5O−Na+ + CH3I → C6H5OCH3 + NaI
Molecular formula C7H8O
Molecular weight 108.14
CAS number 100-66-3
EINECS number 202-876-1
Specifications
Appearance Clear, colourless liquid
Purity (by GC) 99.5% minimum
Moisture (by KF) 0.3% maximum
Physical properties
Boiling point 154°C
Specific gravity 0.995 at 20°C
Solubility in water Insoluble
Description
Anisole is a clear, colourless liquid.
Applications
Intermediate for perfumery and pharmaceutical products
Storage and handling
Store in a properly labeled and tightly closed container in a cool and well-ventilated area.
Keep the container away from heat and other possible sources of ignition.
Handle in accordance with good industrial hygiene and safety practices.
Containers that are opened must be carefully resealed and kept upright to prevent leakage.
Wear suitable protective clothing and personal protective equipment (PPE).
In case of insufficient ventilation, wear suitable respiratory equipment.
Avoid contact with skin and eyes.
Always refer to the Safety Data Sheet (SDS) for detailed information on storage and handling.
Anisole, PhOMe, is a weakly polar aprotic solvent with an electric permittivity, εs, equal to 4.33, which allows one to obtain excellent cyclic voltammetric curves at electrodes of conventional size but has a Pekar factor almost two times lower than THF and CH2Cl2 resulting in a lower solvent reorganization energy for electron transfer processes.
Electrochemistry in anisole of a number of π-electron systems: ferrocene, anthracene, 1-chloro- and 9-chloroanthracene, is described.
Anisole finds applications in various sectors including perfumes, pharmaceuticals, and other application including food & beverages and dyes.
Perfume was the largest application segment in 2014 accounting for over 50% of global revenue and is expected to grow significantly as a result of high consumption owing to its pleasant and sweet properties.
Robust manufacturing base of cosmetic industry coupled with growing domestic demand in U.S., China, Germany, Saudi Arabia, Italy, Mexico, Brazil, France and the UK is expected to augment industry growth over the forecast period
Product use in the pharmaceuticals sector is expected to grow at CAGR of over 4.2% from 2015 to 2022 in light of high growth in China and India on account of favorable FDI policies.
Moreover, growing domestic demand in developing countries due to increasing health awareness coupled with technological advancement is expected to further drive pharmaceutical industry, contributing to market growth over the next seven years.
IUPAC names:
Anisol
ANISOL
Anisole
anisole
Anisole
anisole
Fenil metil eter
Methoxybenzene
methoxybenzene
Metoxybenzene
SYNONYMS:
ANISOLE
Methoxybenzene
100-66-3
Benzene, methoxy-
Methyl phenyl ether
Anisol
Phenyl methyl ether
Phenoxymethane
Anizol
Phenol methyl ether
Methoxy-Benzene
4-methoxybenzene
HSDB 44
UNII-B3W693GAZH
NSC 7920
Ether, methyl phenyl-
MFCD00008354
B3W693GAZH
CHEBI:16579
4-methoxy-benzene
Anisole, 99%, pure
Benzene, methoxy
Ether, methyl phenyl
FEMA Number 2097
Anisole, 99%, Extra Dry, AcroSeal(R)
FEMA No. 2097
EINECS 202-876-1
UN2222
Anisloe
anisole
AI3-00042
methylphenyl ether
4-methoxy benzene
Anethole,(S)
Methyl phenyl-Ether
Anisole, 8CI
Anisole Methoxybenzene
Methoxy-Benzeneanisole
154492-88-3
Anisole-[13C
PubChem12830
Methoxy-benzene (anisol)
bmse010217
EC 202-876-1
SCHEMBL1205
WLN: 1O
Anisole, analytical standard
ACMC-1C6S9
[C]OC1=CC=CC=C1
Anisole, anhydrous, 99.7%
SCHEMBL497674
AQUALINE STANDARD 1.0
Methoxybenzine
Anisole, SuperDry, J&KSeal
Benzene,methoxy-
Ether, methyl phenyl-
ether,methylphenyl
femanumber:2097
methoxy-benzen
Phenoxymethane
Anisole;Methoxybenzene
Methyoxybenzine
ANISOLE, STANDARD FOR GC
ANISOLE 99+% FCC
ANISOLE, ANHYDROUS, 99.7%
ANISOLE, REAGENTPLUS, 99%
ANISOLE REAGENTPLUS 99%
ANISLOE
ANISOLE FOR SYNTHESIS
Methoxybenzene=Anisole
Anisole( 99%, HyDry, with molecular sieves, Water≤50 ppm (by K.F.))
Anisole(99%, HyDry, Water≤50 ppm (by K.F.))
Esomeprazole Impurity 86
Anisole (liquid) Methoxybenzene
Anisole (liquid)
Anisole, 99%, SpcDry, Water≤50 ppM (by K.F.), SpcSeal
Anisole ReagentPlus(R), 99%
METHYL PHENYL ETHER
AQUALINE STANDARD 1.0
FEMA 2097
MOB
PHENOL METHYL ETHER
Phenyl methyl ether
ANISOL
ANISOLE
METHOXYBENZENE
Anizol
benzene,methoxy
ANISOLE, REAG.
Amisale
Anisole (technical)
Methoxybenzene (technical)
Methyl phenyl ether (technical)
Anisole, extra pure, 99%
ANISOLE,REAGENT
7) ANISOLE
Anisole: (Anisole anhydrous: Methoxybenzene)
ANISOLE extrapure AR
Methoxybenzene, Methyl phenyl ether
Anisole，Anethole，Methoxybenzene，Phenol methyl ether
Anisole ,99%
ANISOLE, 99%, EXTRA PURE
Anisole,Methoxybenzene, Methyl phenyl ether
Anisole, synthesis grade
Anisole (1.2 mL/ampule
Anisole, 99%, pure
Anisole, extra pure, 99% 1LT
Anisole, 99.7%, SuperDry, water≤20 ppm, J&KSeal
ANISODUSACUTANGULUSEXTRACT
Phloroglucinol Impurity 41
