| Revision as of 14:06, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 456618252 of page 1,2-Difluorobenzene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 00:40, 12 May 2024 edit LaundryPizza03 (talk | contribs)Extended confirmed users54,395 edits removed Category:Aromatic compounds; added Category:Simple aromatic rings using HotCat |
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{{chembox |
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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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| Watchedfields = changed |
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| verifiedrevid = 443254122 |
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| verifiedrevid = 477185111 |
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| Reference = <ref>David R. Lide, ed., CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009), CRC Press/Taylor and Francis, Boca Raton, FL.</ref> |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = 1,2-dihydro-1,2-azaborine-2D-skeletal.png |
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| ImageFile = O-Difluorobenzene.svg |
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| ImageSize = 135px |
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| ImageSizeL1 = 125 |
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| ImageAltL1 = Skeletal formula of 1,2-dihydro-1,2-azaborine |
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| IUPACName = 1,2-difluoro-benzene |
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| ImageFileR1 = 1,2-Dihydro-1,2-azaborine-3D-balls.png |
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| OtherNames = 1,2-difluoro-benzene, o-difluorobenzene, ortho-difluorobenzene |
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| ImageSizeR1 = 125 |
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| Section1 = {{Chembox Identifiers |
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| ImageAltR1 = Ball-and-stick model of the 1,2-dihydro-1,2-azaborine molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = 1,2-Dihydro-1,2-azaborine |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38583 |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 9325 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| InChI = 1/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| CASNo = 6680-69-9 |
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| InChIKey = GOYDNIKZWGIXJT-UHFFFAOYAN |
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| PubChem = 12300196 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem_Comment = PubChem has wrong formula |
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| StdInChI = 1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 24769701 |
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| StdInChIKey = GOYDNIKZWGIXJT-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C4H6BN/c1-2-4-6-5-3-1/h1-6H |
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| CASNo = <!-- blanked - oldvalue: 367-11-3 --> |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem = 9706 |
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| StdInChIKey = OGZZEGWWYQKMSO-UHFFFAOYSA-N |
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| SMILES = Fc1ccccc1F |
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| SMILES = C1=CC=CNB1}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>4</sub>F<sub>2</sub> |
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| Formula = C{{sub|4}}H{{sub|6}}BN |
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| MolarMass = 114.093 g/mol |
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| MolarMass = 78.908 g mol{{sup|−1}} |
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| Appearance = colorless liquid |
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| Appearance = clear, colorless liquid |
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| Density = 1.1599 g/cm<sup>3</sup> |
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| Density = |
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| MeltingPt = −46 to −45 °C. |
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| MeltingPtC = -34 |
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| BoilingPtC = 92 |
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| BoilingPt = |
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| Solubility = (insoluble) 1.14 g/L}} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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'''1,2-Dihydro-1,2-azaborine''' is an ] ] with properties intermediate between ] and ]. Its chemical formula is C{{sub|4}}BNH{{sub|6}}. It resembles a benzene ring, except that two adjacent carbons are replaced by nitrogen and boron, respectively. |
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== Preparation == |
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After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.<ref>Stu Borman. "Long-Sought Benzenelike Molecule Created: Aromaticity of organic-inorganic hybrid resembles benzene's." '']'' January 5, 2009 Volume 87, Number 01 p. 11</ref><ref>{{ cite journal | journal = ] | volume = 48 | issue = 5 |date=January 2009 | pages = 973–977 | doi = 10.1002/anie.200805554 | title = A Hybrid Organic/Inorganic Benzene | author = A. J. V. Marwitz | author2 = M. H. Matus | author3 = L. N. Zakharov| author4 = D. A. Dixon | author5 = S.-Y. Liu | pmid = 19105174 | doi-access = free }}</ref> |
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One of the synthetic steps is a ] (RCM) reaction:<ref>TBS = ], step 2 RCM = ] using ], step 3 ] using ], step 4 reduction ], step 5 conversion to ] as ] with ] derivative, step 6 cleavage N-TBS bond ], step 7 deprotection with ]</ref> |
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] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Dihydro-1, 2-azaborine, 1, 2-}} |
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] |
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] |
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] |
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] |