| Revision as of 16:13, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465357645 of page 1,2-Dimethoxybenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:19, 11 April 2024 edit Ptrnext (talk | contribs)Extended confirmed users12,654 edits +wlTag: 2017 wikitext editor |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443254229 |
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| verifiedrevid = 477203820 |
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| Name = 1,2-Dimethoxybenzene |
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| Name = 1,2-Dimethoxybenzene |
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| ImageFile = Veratrole.svg |
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| ImageFile = Veratrole.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageName = 1,2-Dimethoxybenzene |
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| ImageName = 1,2-Dimethoxybenzene |
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| IUPACName = 1,2-Dimethoxybenzene |
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| ImageFile1 = 1,2-Dimethoxybenzene-3D-balls.png |
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| ImageSize1 = 160 |
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| OtherNames = veratrole<br />''o''-dimethoxybenzene<br />pyrocatechol dimethyl ether |
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| ImageAlt1 = 1,2-Dimethoxybenzene molecule |
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| Section1 = {{Chembox Identifiers |
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| PIN = 1,2-Dimethoxybenzene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 702 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}}</ref> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = Veratrole<br />''o''-Dimethoxybenzene<br />Pyrocatechol dimethyl ether |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 59114 |
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| ChEBI = 59114 |
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| ChemSpiderID = 13861009 |
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| ChemSpiderID = 13861009 |
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| PubChem = 7043 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 61WJZ2Q41I |
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| UNII = 61WJZ2Q41I |
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| EC_number = 202-045-3 |
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| ChEMBL = 1668603 |
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| InChI = 1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 |
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| InChI = 1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 |
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| SMILES1 = COc1ccccc1OC |
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| InChIKey = ABDKAPXRBAPSQN-UHFFFAOYAD |
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| InChIKey = ABDKAPXRBAPSQN-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ABDKAPXRBAPSQN-UHFFFAOYSA-N |
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| StdInChIKey = ABDKAPXRBAPSQN-UHFFFAOYSA-N |
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| CASNo = 91-16-7 |
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| CASNo = 91-16-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = COc1ccccc1OC |
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| SMILES = COc1ccccc1OC |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8 | H=10 | O=2 |
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| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub> |
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| Density = 1.084 g/cm{{sup|3}}<ref name="Merck Index">''Merck Index'', 11th Edition, '''9857'''</ref> |
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| MolarMass = 138.16 g/mol |
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| MeltingPtC = 22–23 |
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| Density = 1.084 g/cm³ |
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| MeltingPt_ref = <ref name="Merck Index"/> |
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| MeltingPt = 22–23 °C |
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| BoilingPt = 206–207 °C |
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| BoilingPtC = 206–207 |
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| BoilingPt_ref = <ref name="Merck Index"/> |
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| MagSus = -87.39·10{{sup|−6}} cm{{sup|3}}/mol |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| NFPA-H = 2 |
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| GHSSignalWord = Warning |
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| NFPA-F = 2 |
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| HPhrases = {{H-phrases|302}} |
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| NFPA-R = |
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| PPhrases = {{P-phrases|264|270|301+312|330|501}} |
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| NFPA-H = 2 |
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| NFPA-F = 2 |
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| NFPA-R = |
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'''1,2-Dimethoxybenzene''', commonly known as '''veratrole''', is an ] with the ] C{{sub|6}}H{{sub|4}}(]){{sub|2}}. It is one of three isomers of ]. It is a colorless liquid, with a pleasant odor and slight solubility in water. It is the dimethyl ] derived from ]. |
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==Occurrence== |
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1,2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of ] by ].<ref name="ReferenceA">{{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}}</ref> 1,2-Dimethoxybenzene is an insect attractant.<ref name="ReferenceA"/> Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.<ref name="ReferenceA"/> |
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==Uses == |
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1,2-Dimethoxybenzene is a building block for the ] of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes ].<ref>{{OrgSynth | title = 4-Iodoveratrole | author = Janssen, D. E. | author2 = Wilson, C. V. | collvol = 4 | collvolpages = 547 | year = 1963 | prep = CV4P0547}}</ref> |
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An example of the use of veratrole is in the synthesis of ].<ref>{{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}}</ref> |
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Veratrole can easily be brominated with ] to give 4-bromoveratrole.<ref name="BannardLatremouille1953">{{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}}</ref> |
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== Related compounds == |
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* ] |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Dimethoxybenzene, 1, 2-}} |
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] |