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1,2-Dimethoxybenzene

o-Dimethoxybenzene Pyrocatechol dimethyl ether | NFPA-H = 2 | NFPA-F = 2 | NFPA-R =

1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula CH(OCH). 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. 1,2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.

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.

An example of the use of veratrole is in the synthesis of Domipizone.

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

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. ''Merck Index'', 11th Edition, '''9857'''
  3. (2012). "Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction". BMC Plant Biology.
  4. Janssen, D. E.. (1963). "4-Iodoveratrole".
  5. "Tetrahydropyridazinone derivatives, process for their preparation and their use".
  6. (1953). "4-BROMOVERATROLE". Canadian Journal of Chemistry.
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