1,2-Dimethoxybenzene

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1,2-Dimethoxybenzene
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Density 1.084 g/cm3[2]
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Template:Longitem −87.39·10−6 cm3/mol

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1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a colorless liquid, with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol.

Occurrence

1,2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase.[3] 1,2-Dimethoxybenzene is an insect attractant.[3] Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.[3]

Uses

1,2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution.[4]

An example of the use of veratrole is in the synthesis of Domipizone.[5]

Veratrole can easily be brominated with NBS to give 4-bromoveratrole.[6]

Related compounds

References

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