|Jmol-3D images||Image 1
|Molar mass||108.14 g mol−1|
|Melting point||−37 °C; −35 °F; 236 K|
|Boiling point||154 °C; 309 °F; 427 K|
|LD50||3700 mg/kg (rat, oral)|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.
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
- C6H5O−Na+ + CH3Br → CH3OC6H5 + NaBr
- Butylated hydroxyanisole
- Ethyl phenyl ether
- 2,4,6-Trichloroanisole (cork taint)
- G. S. Hiers and F. D. Hager (1941), "Anisole", Org. Synth.; Coll. Vol. 1: 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