CAS number 100-66-3 YesY
ChemSpider 7238 YesY
KEGG C01403 YesY
ChEBI CHEBI:16579 YesY
Jmol-3D images Image 1
Image 2
Molecular formula C7H8O
Molar mass 108.14 g/mol
Appearance colorless liquid
Density 0.995 g cm−3
Melting point

−37 °C, 236 K, -35 °F

Boiling point

154 °C, 427 K, 309 °F

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Anisole, or methoxybenzene, is the organic compound with the formula CH3OC6H5. It 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 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, more so than the inductive effect of the electronegative oxygen.

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, [(CH3O6H4)PS2]2.

The ether linkage is highly stable, but the methyl group can be removed with hydroiodic acid:

CH3OC6H5 + HI → HOC6H5 + CH3I


Anisole is prepared by the Williamson ether synthesis, reacting sodium phenoxide with a methyl bromide and related methylating reagents:[1]

C6H5ONa+ + CH3Br → CH3OC6H5 + NaBr


Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals.[2] For example, synthetic anethole is prepared from anisole.


Anisole is relatively nontoxic with an LD50 of 3700 mg/kg in rats.[3]

See also


  1. ^ G. S. Hiers and F. D. Hager (1941), "Anisole", Org. Synth., ; Coll. Vol. 1: 58 
  2. ^ Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus “Phenol Derivatives“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_313
  3. ^ MSDS; its main hazard is its flammabiliy.[1]

External links

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Look at other dictionaries:

  • Anisole — Général Nom IUPAC méthoxybenzene No CAS …   Wikipédia en Français

  • anisole — ● anisole nom masculin Éther méthylique du phénol, CH3O―C6H5, bon solvant des composés organiques et intermédiaire industriel …   Encyclopédie Universelle

  • anisole — [an′i sōl΄] n. [Fr anisol < anis (see ANISE) + ol, OLE] a colorless, fragrant liquid, C6H5OCH3, made by heating phenol with methyl alcohol: it is used in making perfumes …   English World dictionary

  • anisole — Anisol An i*sol anisole anisole, n. [Anisic + ol.] (Chem.) Methyl phenyl ether, {C6H5.O.CH3}, got by distilling anisic acid or by the action of methide on potassium phenolate. [Webster 1913 Suppl.] …   The Collaborative International Dictionary of English

  • anisole — anizolas statusas T sritis chemija formulė CH₃OC₆H₅ atitikmenys: angl. anisole rus. анизол ryšiai: sinonimas – metoksibenzenas …   Chemijos terminų aiškinamasis žodynas

  • anisole — /an euh sohl /, n. Chem. a colorless, water insoluble liquid, C7H8O, having a pleasant, aromatic odor, used chiefly in perfumery and organic synthesis, and as a vermicide. Also called methyl phenyl ether, methoxybenzene. [1860 65; ANISE + OLE2] * …   Universalium

  • anisole — noun The aromatic ether methoxybenzene; it is used in perfumery and in organic synthesis; and derivative of this compound Syn: anisol …   Wiktionary

  • anisole — Obtained from anisic acid; used in perfumery …   Medical dictionary

  • anisole — n. chemical substance used in perfumes and organic synthesis …   English contemporary dictionary

  • anisole — an·is·ole …   English syllables

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