1,2-Dimethoxybenzene

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1,2-Dimethoxybenzene
1,2-Dimethoxybenzene
1,2-Dimethoxybenzene molecule
Identifiers
CAS number 91-16-7 YesY
ChemSpider 13861009 YesY
UNII 61WJZ2Q41I YesY
ChEBI CHEBI:59114 YesY
Jmol-3D images Image 1
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Properties
Molecular formula C8H10O2
Molar mass 138.16 g/mol
Density 1.084 g/cm³
Melting point 22–23 °C
Boiling point 206–207 °C
Hazards
NFPA 704
Flammability code 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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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.

Uses and occurrence[edit]

Veratrole is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution.[1]

It is a naturally occurring and functions as an insect attractant. Its biosynthesis entails the enzyme-catalyzed methylation of guaiacol (methoxyphenol).[2]

Related compounds[edit]

Veratrole is synthesized by methylation of guaiacol in plants.[3]

Literature[edit]

  • Merck Index, 11th Edition, 9857.

References[edit]

  1. ^ Janssen, D. E.; Wilson, C. V. (1963), "4-Iodoveratrole", Org. Synth. ; Coll. Vol. 4: 547 
  2. ^ Gupta, A. K., Akhtar, T. A., Widmer, A., Pichersky, E., & Schiestl, F. 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, volume 12, 158. doi:10.1186/1471-2229-12-158
  3. ^ Gupta, A. K., Akhtar, T. A., Widmer, A., Pichersky, E., & Schiestl, F. 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, volume 12, 158. doi:10.1186/1471-2229-12-158