1,2-Dimethoxybenzene
Names | |
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IUPAC name
1,2-Dimethoxybenzene | |
Other names
Veratrole o-Dimethoxybenzene Pyrocatechol dimethyl ether | |
Identifiers | |
91-16-7 | |
3D model (Jmol) | Interactive image Interactive image |
ChEBI | CHEBI:59114 |
ChemSpider | 13861009 |
ECHA InfoCard | 100.001.860 |
UNII | 61WJZ2Q41I |
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Properties | |
C8H10O2 | |
Molar mass | 138.17 g·mol−1 |
Density | 1.084 g/cm³[1] |
Melting point | 22–23 °C (72–73 °F; 295–296 K) [1] |
Boiling point | 206–207 °C (403–405 °F; 479–480 K) [1] |
Hazards | |
NFPA 704 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
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.[2] 1,2-Dimethoxybenzene is an insect attractant.[2] Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.[2]
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.[3]
An example of the use of veratrole is in the synthesis of Domipizone.[4]
Related compounds
- 1,3-Dimethoxybenzene
- 1,4-Dimethoxybenzene
References
- 1 2 3 Merck Index, 11th Edition, 9857
- 1 2 3 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.
- ↑ Janssen, D. E.; Wilson, C. V. (1963). "4-Iodoveratrole". Org. Synth.; Coll. Vol., 4, p. 547
- ↑ EP 0129791, (1985); CA, 102, 220886 (synth, pharmacol).