Wikipedia

1,2-Dimethoxybenzene

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.

1,2-Dimethoxybenzene
1,2-Dimethoxybenzene
1,2-Dimethoxybenzene molecule
Names
Preferred IUPAC name
1,2-Dimethoxybenzene[1]
Other names
Veratrole
o-Dimethoxybenzene
Pyrocatechol dimethyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.860 Edit this at Wikidata
EC Number
  • 202-045-3
UNII
  • InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 checkY
    Key: ABDKAPXRBAPSQN-UHFFFAOYSA-N checkY
  • InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
    Key: ABDKAPXRBAPSQN-UHFFFAOYAD
  • COc1ccccc1OC
Properties
C8H10O2
Molar mass 138.166 g·mol−1
Density 1.084 g/cm3[2]
Melting point 22–23 °C (72–73 °F; 295–296 K)[2]
Boiling point 206–207 °C (403–405 °F; 479–480 K)[2]
-87.39·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence

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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

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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]

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References

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  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.
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