1,2-Dimethoxybenzene

1,2-Dimethoxybenzene

Names
IUPAC name 1,2-Dimethoxybenzene
Other names Veratrole o-Dimethoxybenzene Pyrocatechol dimethyl ether
Identifiers
CAS Number	91-16-7 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:59114 Y
ChemSpider	13861009 Y
ECHA InfoCard	100.001.860
UNII	61WJZ2Q41I Y
InChI InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 Y Key: ABDKAPXRBAPSQN-UHFFFAOYSA-N Y InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 Key: ABDKAPXRBAPSQN-UHFFFAOYAD
SMILES COc1ccccc1OC COc1ccccc1OC
Properties
Chemical formula	C8H10O2
Molar mass	138.17 g·mol−1
Density	1.084 g/cm3
Melting point	22–23 °C (72–73 °F; 295–296 K)
Boiling point	206–207 °C (403–405 °F; 479–480 K)
Magnetic susceptibility (χ)	-87.39·10−6 cm3/mol
Hazards
NFPA 704	2 2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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.

1,2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase. 1,2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.

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.

An example of the use of veratrole is in the synthesis of Domipizone.

Veratrole can easily be brominated with NBS to give 4-bromoveratrole.