Anisole, or methoxybenzene, is an 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. It is an ether.
|Preferred IUPAC name
|Systematic IUPAC name
Methyl phenyl ether
3D model (JSmol)
|Molar mass||g·mol−1 108.140|
|Melting point||−37 °C (−35 °F; 236 K)|
|Boiling point||154 °C (309 °F; 427 K)|
|GHS signal word||Warning|
|H226, H315, H319|
|P210, P233, P240, P241, P242, P243, P264, P280, P302+352, P303+361+353, P305+351+338, P321, P332+313, P337+313, P362, P370+378, P403+235, P501|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|3700 mg/kg (rat, oral)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
It can be prepared by the Williamson ether synthesis; sodium phenoxide is reacted with a methyl halide to yield 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 as a mesomeric electron donor, more so than as an inductive electron withdrawing group despite the electronegativity of the oxygen.
- 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.
- CH3OC6H5 + HI → HOC6H5 + CH3I
- 2 C6H5O−Na+ + (CH3O)2SO2 → 2 C6H5OCH3 + Na2SO4
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 702–703. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
Anisole, C6H5-O-CH3, is the only name in the class of ethers which is retained both as a preferred IUPAC name and for use in general nomenclature. For preferred IUPAC names, no substitution is allowed; for general nomenclature substitution is allowed on the ring and on the side chain under certain conditions (see P-18.104.22.168).
- G. S. Hiers and F. D. Hager (1941). "Anisole". Organic Syntheses.; Collective Volume, 1, p. 58
- 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
- MSDS Archived July 1, 2010, at the Wayback Machine