1,2-Dimethoxybenzene

1,2-Dimethoxybenzene

1,2-Dimethoxybenzene
Names
Preferred IUPAC name 1,2-Dimethoxybenzene[1]
Other names Veratrole o-Dimethoxybenzene Pyrocatechol dimethyl ether
Identifiers
CAS Number	91-16-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:59114^Y
ChEMBL	ChEMBL1668603
ChemSpider	13861009^Y
ECHA InfoCard	100.001.860
EC Number	202-045-3
PubChem CID	7043
UNII	61WJZ2Q41I^Y
CompTox Dashboard (EPA)	DTXSID7047065
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
Properties
Chemical formula	C8H10O2
Molar mass	138.166 g·mol^−1
Density	1.084 g/cm^3[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]
Magnetic susceptibility (χ)	-87.39·10^−6 cm^3/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)	2 2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C₆H₄(OCH₃)₂. It is one of three isomers of dimethoxybenzene. 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

• 1,3-Dimethoxybenzene
• 1,4-Dimethoxybenzene
• Methyl isoeugenol

References

1. 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.
2. Merck Index, 11th Edition, 9857
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.
4. Janssen, D. E.; Wilson, C. V. (1963). "4-Iodoveratrole". Organic Syntheses; Collected Volumes, vol. 4, p. 547.
5. EP 0129791, Zoller, Gerhard; Beyerle, Rudi & Just, Melitta et al., "Tetrahydropyridazinone derivatives, process for their preparation and their use", published 985-01-02, assigned to Cassella AG 
6. Bannard, R. A. B.; Latremouille, G. (1953). "4-BROMOVERATROLE". Canadian Journal of Chemistry. 31 (4): 469. doi:10.1139/v53-062. ISSN 0008-4042.