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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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| Verifiedfields = changed |
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| verifiedrevid = 442344841 |
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| Watchedfields = changed |
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| ImageFileL1 = 1,3-Benzodioxole.png |
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| verifiedrevid = 477204881 |
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| ImageFileL1 = Benzo(d)(1,3)dioxole 200.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 121 |
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| ImageNameL1 = Kekulé, skeletal formula of 1,3-benzodioxole |
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| ImageNameL1 = Kekulé, skeletal formula of 1,3-benzodioxole |
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| ImageFileR1 = 1,3-Benzodioxole-3D-balls.png |
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| ImageFileR1 = 1,3-Benzodioxole-3D-balls.png |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeR1 = 121 |
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| ImageNameR1 = Ball and stick model of 1,3-benzodioxole |
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| ImageNameR1 = Ball and stick model of 1,3-benzodioxole |
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| PIN = 2''H''-1,3-Benzodioxole |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 1,3-Benzodioxole<br />Benzodioxole<br />1,2-benzene<br />1,2-Methylenedioxybenzene |
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| CASNo = <!-- blanked - oldvalue: 274-09-9 --> |
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|Section1={{Chembox Identifiers |
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| PubChem = 9229 |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 274-09-9 |
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| ChemSpiderID = 13881169 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 205-992-0 |
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| UNII = F0XLL582B8 |
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| UNNumber = 1993 |
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| PubChem = 9229 |
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| ChemSpiderID = 13881169 |
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| MeSHName = 1,3-Benzodioxole |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 205-992-0 |
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| UNNumber = 1993 |
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| MeSHName = 1,3-Benzodioxole |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38732 |
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| ChEBI = 38732 |
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| RTECS = DA5600000 |
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| RTECS = DA5600000 |
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| Beilstein = 115506 |
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| Beilstein = 115506 |
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| SMILES = C1Oc2ccccc2O1 |
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| SMILES = C1Oc2ccccc2O1 |
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| SMILES1 = C1OC2=C(O1)C=CC=C2 |
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| SMILES1 = C1OC2=C(O1)C=CC=C2 |
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| StdInChI = 1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 |
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| StdInChI = 1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 |
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| InChI = 1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 |
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| StdInChIKey = FTNJQNQLEGKTGD-UHFFFAOYSA-N |
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| StdInChIKey = FTNJQNQLEGKTGD-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = FTNJQNQLEGKTGD-UHFFFAOYAV |
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| InChIKey = FTNJQNQLEGKTGD-UHFFFAOYAV |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 7 |
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| C=7 | H=6 | O=2 |
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| Density = 1.064 g cm{{sup|−3}} |
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| H = 6 |
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| O = 2 |
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| BoilingPtC = 172-173 |
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| LogP = 2.08 |
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| ExactMass = 122.036779436 g mol<sup>-1</sup> |
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| VaporPressure = 1.6 kPa |
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| Density = 1.064 g cm<sup>-3</sup> |
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| BoilingPtK = 446 |
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| LogP = 2.08 |
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| VaporPressure = 1.6 kPa |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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|Section3={{Chembox Thermochemistry |
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| DeltaHc = -3.428 MJ mol<sup>-1</sup> |
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| DeltaHc = -3.428 MJ mol{{sup|−1}} |
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}} |
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| Section4 = {{Chembox Hazards |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS exclamation mark}} |
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| GHSPictograms = {{GHS exclamation mark}} |
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| GHSSignalWord = '''WARNING''' |
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| GHSSignalWord = '''WARNING''' |
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| HPhrases = {{H-phrases|302|332}} |
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| HPhrases = {{H-phrases|302|332}} |
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| NFPA-F = 2 |
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| EUClass = {{Hazchem Xn}} |
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| RPhrases = {{R20/22}} |
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| NFPA-H = 1 |
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| NFPA-R = 0 |
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| SPhrases = {{S22}}, {{S24/25}} |
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| NFPA-F = 2 |
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| FlashPtC = 61 |
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| NFPA-H = 1 |
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| NFPA-R = 0 |
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| FlashPt = 61 °C |
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}} |
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'''1,3-Benzodioxole''' ('''1,2-methylenedioxybenzene''') is an ] with the formula C{{sub|6}}H{{sub|4}}O{{sub|2}}CH{{sub|2}}. The compound is classified as ] derivative and a ] containing the ] ]. It is a colorless liquid. |
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Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.<ref>Murray, M., "Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation", Curr. Drug Metab. 2000, volume 1, 67-84. {{doi|10.2174/1389200003339270}}</ref> |
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==Preparation== |
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1,3-Benzodioxole can be synthesized from ] with ].<ref>{{cite journal|author=Bonthrone, W.|author2=Cornforth, J.|name-list-style=amp|title=The methylenation of catechols|journal=Journal of the Chemical Society|issue=9|year=1969|pages=1202–1204|doi=10.1039/J39690001202|url=http://pubs.rsc.org/en/content/articlelanding/1969/J3/j39690001202|accessdate=28 December 2013}}</ref><ref>{{cite journal|author=Fujita, Harushige|author2=Yamashita|name-list-style=amp|author3=Masataro|title=The Methylenation of Several Allylbenzene-1,2-diol Derivatives in Aprotic Polar Solvents|journal=Bulletin of the Chemical Society of Japan|year=1973|volume=46|issue=11|pages=3553–3554|doi=10.1246/bcsj.46.3553|url=https://www.jstage.jst.go.jp/article/bcsj1926/46/11/46_11_3553/_article|accessdate=27 December 2013|doi-access=free}}</ref> |
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== See also == |
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* ] |
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* ] |
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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:Benzodioxole, 1, 3-}} |
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] |
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{{heterocyclic-stub}} |