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

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 702. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ a b c Merck Index, 11th Edition, 9857
  3. ^ a b c Gupta, Alok K; Akhtar, Tariq A; Widmer, Alex; Pichersky, Eran; Schiestl, Florian P (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. 12: 158. doi:10.1186/1471-2229-12-158. PMC 3492160. PMID 22937972.
  4. ^ Janssen, D. E.; Wilson, C. V. (1963). "4-Iodoveratrole". Organic Syntheses; Collected Volumes, vol. 4, p. 547.
  5. ^ EP 0129791, Zoller, Gerhard; Beyerle, Rudi & Just, Melitta et al., "Tetrahydropyridazinone derivatives, process for their preparation and their use", published 985-01-02, assigned to Cassella AG 
  6. ^ Bannard, R. A. B.; Latremouille, G. (1953). "4-BROMOVERATROLE". Canadian Journal of Chemistry. 31 (4): 469. doi:10.1139/v53-062. ISSN 0008-4042.