Anisole

Anisole

Systematic name	Methoxybenzene
Molecular formula	C₆H₅OCH₃
Molar mass	108.14 g/mol
CAS number	[100-66-3]
Density	0.995 g/ml
Melting point	−37 °C
Boiling point	154 °C
SMILES	COc1ccccc1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Anisole, also known as methoxybenzene, is a colorless liquid with a pleasant smell similar to that of anise seed. 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 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.