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
Image 2
Properties
Molecular formula C8H10O2
Molar mass 138.16 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
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.

Occurrence[edit]

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]

Uses[edit]

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]

Related compounds[edit]

References[edit]

  1. ^ a b c Merck Index, 11th Edition, 9857
  2. ^ a b 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. 
  3. ^ Janssen, D. E.; Wilson, C. V. (1963), "4-Iodoveratrole", Org. Synth. ; Coll. Vol. 4: 547