Anisole

Anisole

Names
IUPAC name Anisole
Preferred IUPAC name Methoxybenzene
Systematic IUPAC name Methoxybenzene
Other names Methyl phenyl ether Phenoxymethane
Properties
Chemical formula	C7H8O
Molar mass	108.14 g/mol
Appearance	Colorless liquid
Odor	Anise-like
Density	0.995 g/cm3
Melting point	−37 °C (−35 °F; 236 K)
Boiling point	154 °C (309 °F; 427 K)
Solubility in water	0.171 g/ 100 ml (20 °C)
Solubility	Miscible in acetone, alcohols, ethers
Vapor pressure	3.54 mmHg (at 25 °C)
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	52 °C (125 °F; 325 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	3,700 mg/kg (rat, oral)
Related compounds
Related compounds	Phenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Anisole or methoxybenzene, is an organic compound with the formula CH₃OC₆H₅. It is used as a precursor in the production of perfumes and other pharmaceuticals.

Properties

Chemical

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.

Physical

Anisole is a colorless or straw-colored liquid, with an odor reminiscent of anise, almost insoluble in water, but soluble in other organic solvents, like acetone or alcohols.

Availability

Anisole is sold by chemical suppliers, and can be bought online.

Preparation

Anisole is best prepared via the Williamson ether synthesis, by reacting sodium phenoxide with methyl iodide.

C₆H₅O⁻Na⁺ + CH₃I → C₆H₅OCH₃ + NaI

Projects

• Make perfumes
• Fragrant compound collection
• Synthesis of trinitroanisole

Handling

Safety

Anisole is relatively nontoxic with an LD50 of 3,700 mg/kg in rats. It may be irritant to skin.

Storage

Anisole is best kept in closed glass bottles with a good lid/stopper.

Disposal

Should be strongly diluted in a more flammable solvent, like ethanol or acetone, then burned.

References

Relevant Sciencemadness threads

• Help on Friedel Crafts alkylation and acylation of anisole and acetophenone