1,2-Dimethoxybenzene
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Names | |
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Preferred IUPAC name
1,2-Dimethoxybenzene[1] | |
Other names
Veratrole
o-Dimethoxybenzene Pyrocatechol dimethyl ether | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.860 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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: | |
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Warning | |
H302 | |
P264, P270, P301+P312, P330, P501 | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. 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
- ^ 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.
- ^ a b c Merck Index, 11th Edition, 9857
- ^ 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.
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: CS1 maint: unflagged free DOI (link) - ^ Janssen, D. E.; Wilson, C. V. (1963). "4-Iodoveratrole". Organic Syntheses; Collected Volumes, vol. 4, p. 547.
- ^ EP 0129791, (1985); CA, 102, 220886 (synth, pharmacol).
- ^ Bannard, R. A. B.; Latremouille, G. (1953). "4-BROMOVERATROLE". Canadian Journal of Chemistry. 31 (4): 469–469. doi:10.1139/v53-062. ISSN 0008-4042.