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					Anisole
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Anisole, or methoxybenzene, is the organic compound with the formula                                           Anisole
CH3 OC 6 H 5 . 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.

    Contents
 1 Reactivity
 2 Preparation
 3 Applications                                                                                             IUPAC name
 4 Safety
                                                                                                          methoxybenzene
 5 See also
                                                                                                            Other names
 6 References
 7 External links                                                                                              anisole
                                                                                                          phenoxymethane
                                                                                                         phenyl methyl ether
Reactivity                                                                                                     Identifiers
Anisole undergoes electrophilic aromatic substitution reaction more quickly than         CAS number               100-66-3
does benzene, which in turn reacts more quickly than nitrobenzene. The methoxy           ChemSpider               7238

group is an ortho/para directing group, which means that electrophilic substitution      UNII                     B3W693GAZH

preferentially occurs at these three sites. The enhanced nucleophilicity of anisole      KEGG                     C01403

vs benzene reflects the influence of the methoxy group, which renders the ring           ChEBI                    CHEBI:16579

more electron-rich. The methoxy group strongly affects the pi cloud of the ring,         ChEMBL                   CHEMBL278024

more so than the inductive effect of the electronegative oxygen.                         Jmol-3D images           Image 1
                                                                                                                  Image 2
Illustrative of its nucleophilicity, anisole reacts with acetic anhydride to give 4-
                                                                                                                SMILES
methoxyacetophenone:
                                                                                         O(c1ccccc1)C
   CH3 OC 6 H 5 + (CH 3 CO)2 O → CH3 OC 6 H 4 C(O)CH3 + CH3 CO 2 H
                                                                                         COc1ccccc1
Unlike most acetophenones, but reflecting the influence of the methoxy group,
                                                                                                                 InChI
methoxyacetophenone undergoes a second acetylation. Many related reactions
                                                                                         InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-
have been demonstrated. For example, P4 S10 converts anisole to Lawesson's
                                                                                         6H,1H3
reagent, [(CH3 OC 6 H 4 )PS2 ]2 .                                                        Key: RDOXTESZEPMUJZ-UHFFFAOYSA-N
The ether linkage is highly stable, but the methyl group can be removed with             InChI=1/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
hydroiodic acid:                                                                         Key: RDOXTESZEPMUJZ-UHFFFAOYAP
   CH3 OC 6 H 5  + HI → HOC6 H 5 + CH3 I                                                                      Properties
                                                                                         Molecular formula        C7 H8 O
Preparation                                                                              Molar mass               108.14 g/mol
                                                                                         Appearance               colorless liquid
Anisole is prepared by the Williamson ether synthesis, reacting sodium phenoxide
                                                                                         Density                  0.995 g cm −3
with methyl bromide and related methylating reagents: [1]
                                                                                         Melting point            −37 °C, 236 K, -35 °F
   C 6 H 5 O − Na+ + CH3 Br → CH3 OC 6 H 5 + NaBr
                                                                                         Boiling point            154 °C, 427 K, 309 °F
Applications                                                                                              (verify) (what is:   / ?)
                                                                                         Except where noted otherwise, data are given for
Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals.[2]              materials in their standard state (at 25 °C,
For example, synthetic anethole is prepared from anisole.                                                     100 kPa)
                                                                                                          Infobox references
Safety
Anisole is relatively nontoxic with an LD50 of 3700 mg/kg in rats. [3]

See also
   Anethole
   Bromoanisole
   Butylated hydroxyanisole
   Ether
   Ethyl phenyl ether
   Phenol
   2,4,6-Trichloroanisole (cork taint)

References
   1. ^ G. S. Hiers and F. D. Hager (1941), "Anisole" , Org. Synth.; Coll. Vol. 1: 58
   2. ^ 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
   3. ^ MSDS; its main hazard is its flammabiliy.[1]

External links
   International Chemical Safety Card 1014
   Pherobase      pheromone database entry


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