1,2-Dimethoxybenzene
{{chembox
| Watchedfields = changed
| verifiedrevid = 477203820
| Name = 1,2-Dimethoxybenzene
| ImageFile = Veratrole.svg
| ImageSize = 150px
| ImageName = 1,2-Dimethoxybenzene
| ImageFile1 = 1,2-Dimethoxybenzene-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = 1,2-Dimethoxybenzene molecule
| PIN = 1,2-Dimethoxybenzene{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 702 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}}
| OtherNames = Veratrole
o-Dimethoxybenzene
Pyrocatechol dimethyl ether
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 59114
| ChemSpiderID = 13861009
| PubChem = 7043
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 61WJZ2Q41I
| EC_number = 202-045-3
| ChEMBL = 1668603
| InChI = 1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
| InChIKey = ABDKAPXRBAPSQN-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ABDKAPXRBAPSQN-UHFFFAOYSA-N
| CASNo = 91-16-7
| CASNo_Ref = {{cascite|correct|CAS}}
| SMILES = COc1ccccc1OC
}}
|Section2={{Chembox Properties
| C=8 | H=10 | O=2
| Density = 1.084 g/cm{{sup|3}}Merck Index, 11th Edition, 9857
| MeltingPtC = 22–23
| BoilingPtC = 206–207
| MagSus = −87.39·10{{sup|−6}} cm{{sup|3}}/mol
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302}}
| PPhrases = {{P-phrases|264|270|301+312|330|501}}
| NFPA-H = 2
| NFPA-F = 2
| NFPA-R =
}}
}}
1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C{{sub|6}}H{{sub|4}}(methoxy){{sub|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.{{cite journal | doi = 10.1186/1471-2229-12-158| pmid = 22937972| pmc = 3492160| title = Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction| journal = BMC Plant Biology| volume = 12| pages = 158| year = 2012| last1 = Gupta| first1 = Alok K| last2 = Akhtar| first2 = Tariq A| last3 = Widmer| first3 = Alex| last4 = Pichersky| first4 = Eran| last5 = Schiestl| first5 = Florian P| doi-access = free}} 1,2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.
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.{{OrgSynth | title = 4-Iodoveratrole | author = Janssen, D. E. | author2 = Wilson, C. V. | collvol = 4 | collvolpages = 547 | year = 1963 | prep = CV4P0547}}
An example of the use of veratrole is in the synthesis of Domipizone.{{Cite patent|country=EP|number=0129791|title=Tetrahydropyridazinone derivatives, process for their preparation and their use|pubdate=985-01-02 |assign=Cassella AG|inventor1-last=Zoller|inventor1-first= Gerhard |inventor2-last=Beyerle |inventor2-first=Rudi|inventor3-last=Just |inventor3-first=Melitta|inventor4= MARTORANA PIERO; BOHN HELMUT; NITZ ROLF-EBERHARD}}
Veratrole can easily be brominated with NBS to give 4-bromoveratrole.{{cite journal|last1=Bannard|first1=R. A. B.|last2=Latremouille|first2=G.|title=4-BROMOVERATROLE|journal=Canadian Journal of Chemistry|volume=31|issue=4|year=1953|pages=469|issn=0008-4042|doi=10.1139/v53-062|doi-access=free}}