Anisole
| Names | |
|---|---|
| IUPAC name
Anisole
| |
| Preferred IUPAC name
Methoxybenzene | |
| Systematic IUPAC name
Methoxybenzene | |
| Other names
Methyl phenyl ether
Phenoxymethane | |
| Properties | |
| 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) |
| 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.
Contents
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.
