Anisole

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 π 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 reacts with acetic anhydride to give 4-methoxyacetophenone and acetic acid as a byproduct. The reaction of anisole with P4S10 forms Lawesson's reagent an important chemical in phosphorus-sulfur chemistry.