1,2-Dimethoxybenzene

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| 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

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|Section2={{Chembox Properties

| C=8 | H=10 | O=2

| Density = 1.084 g/cm{{sup|3}}Merck Index, 11th Edition, 9857

| MeltingPtC = 22–23

| MeltingPt_ref =

| BoilingPtC = 206–207

| BoilingPt_ref =

| 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 =

}}

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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}}

Related compounds

References

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{{DEFAULTSORT:Dimethoxybenzene, 1, 2-}}

Category:O-methylated natural phenols