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Revision as of 16:20, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456418086 of page 1,3-Benzodioxole for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 19:39, 27 October 2022 edit Citation bot (talk | contribs)Bots5,429,618 edits Misc citation tidying. | Use this bot. Report bugs. | Suggested by AManWithNoPlan | #UCB_CommandLine 
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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.}}
{{Chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 442344841
| Watchedfields = changed
| ImageFileL1 = 1,3-Benzodioxole.png
| verifiedrevid = 477204881
| ImageFileL1 = Benzo(d)(1,3)dioxole 200.svg
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 121
| ImageNameL1 = Kekulé, skeletal formula of 1,3-benzodioxole | ImageNameL1 = Kekulé, skeletal formula of 1,3-benzodioxole
| ImageFileR1 = 1,3-Benzodioxole-3D-balls.png | ImageFileR1 = 1,3-Benzodioxole-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}} | ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageSizeR1 = 121
| ImageNameR1 = Ball and stick model of 1,3-benzodioxole | ImageNameR1 = Ball and stick model of 1,3-benzodioxole
| PIN = 2''H''-1,3-Benzodioxole
| Section1 = {{Chembox Identifiers
| OtherNames = 1,3-Benzodioxole<br />Benzodioxole<br />1,2-benzene<br />1,2-Methylenedioxybenzene
| CASNo = <!-- blanked - oldvalue: 274-09-9 -->
|Section1={{Chembox Identifiers
| PubChem = 9229
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 274-09-9
| ChemSpiderID = 13881169
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 205-992-0 | UNII = F0XLL582B8
| UNNumber = 1993 | PubChem = 9229
| ChemSpiderID = 13881169
| MeSHName = 1,3-Benzodioxole
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 205-992-0
| UNNumber = 1993
| MeSHName = 1,3-Benzodioxole
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 38732 | ChEBI = 38732
| RTECS = DA5600000 | RTECS = DA5600000
| Beilstein = 115506 | Beilstein = 115506
| SMILES = C1Oc2ccccc2O1 | SMILES = C1Oc2ccccc2O1
| SMILES1 = C1OC2=C(O1)C=CC=C2 | SMILES1 = C1OC2=C(O1)C=CC=C2
| StdInChI = 1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 | StdInChI = 1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 | InChI = 1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2
| StdInChIKey = FTNJQNQLEGKTGD-UHFFFAOYSA-N | StdInChIKey = FTNJQNQLEGKTGD-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = FTNJQNQLEGKTGD-UHFFFAOYAV | InChIKey = FTNJQNQLEGKTGD-UHFFFAOYAV
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 7 | C=7 | H=6 | O=2
| Density = 1.064 g cm{{sup|−3}}
| H = 6
| O = 2 | BoilingPtC = 172-173
| LogP = 2.08
| ExactMass = 122.036779436 g mol<sup>-1</sup>
| VaporPressure = 1.6 kPa
| Density = 1.064 g cm<sup>-3</sup>
| BoilingPtK = 446
| LogP = 2.08
| VaporPressure = 1.6 kPa
}} }}
| Section3 = {{Chembox Thermochemistry |Section3={{Chembox Thermochemistry
| DeltaHc = -3.428 MJ mol<sup>-1</sup> | DeltaHc = -3.428 MJ mol{{sup|−1}}
}} }}
| Section4 = {{Chembox Hazards |Section4={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}} | GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING''' | GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302|332}} | HPhrases = {{H-phrases|302|332}}
| NFPA-F = 2
| EUClass = {{Hazchem Xn}}
| RPhrases = {{R20/22}} | NFPA-H = 1
| NFPA-R = 0
| SPhrases = {{S22}}, {{S24/25}}
| NFPA-F = 2 | FlashPtC = 61
| NFPA-H = 1
| NFPA-R = 0
| FlashPt = 61 °C
}} }}
}} }}

'''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.

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>

==Preparation==
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>

== See also ==
* ]
* ]
* ]
* ]
* ]

== References ==
{{Reflist}}

{{DEFAULTSORT:Benzodioxole, 1, 3-}}
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