| Revision as of 16:16, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467588794 of page Xantphos for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 19:26, 24 April 2023 edit Bernardirfan (talk | contribs)Extended confirmed users10,991 edits Clarification |
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{{Distinguish|XPhos}} |
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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 = 446232164 |
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| ImageFile = Xantphos.png |
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| verifiedrevid = 470633169 |
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| ImageFile = Xantphos.svg |
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| ImageSize = 170 |
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| ImageSize = 170 |
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| ImageCaption = Ph stands for ] |
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| ImageFile1 = Xantphos-3D-balls.png |
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| ImageFile1 = Xantphos-based-on-xtal-3D-bs-17.png |
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| ImageSize1 = 220 |
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| ImageSize1 = 220 |
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| PIN = (9,9-Dimethyl-9''H''-xanthene-4,5-diyl)bis(diphenylphosphane) |
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| IUPACName = 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene |
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| OtherNames = Xantphos |
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| OtherNames = Xantphos |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 551930 |
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| ChemSpiderID = 551930 |
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| InChI = 1/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3 |
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| InChI = 1/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CXNIUSPIQKWYAI-UHFFFAOYSA-N |
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| StdInChIKey = CXNIUSPIQKWYAI-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 161265-03-8 --> |
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| CASNo = 161265-03-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 636044 |
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| UNII = NMU72MOG9B |
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| SMILES = O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C |
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| PubChem = 636044 |
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| SMILES = O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>39</sub>H<sub>32</sub>OP<sub>2</sub> |
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| Formula = C<sub>39</sub>H<sub>32</sub>OP<sub>2</sub> |
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| MolarMass = 578.62 g/mol |
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| MolarMass = 578.62 g/mol |
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| Appearance = colorless solid |
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| Appearance = colorless solid |
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| Density = 1.34 g/mL |
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| Density = 1.34 g/mL |
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| MeltingPtCL = 224 |
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| MeltingPtC = 224 to 228 |
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| Solubility = organic solvents |
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| MeltingPtCH = 228 |
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| BoilingPt = |
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| Solubility = organic solvents |
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| MainHazards = flammable |
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| Section3 = {{Chembox Hazards |
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| MainHazards = flammable |
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| FlashPt = |
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| Autoignition = |
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'''Xantphos''' is an ] derived from the ] ]. It is used as a bidentate ] ] and is noteworthy for having a particularly wide ] (108°).<ref>{{cite journal |last1=Birkholz|first1=Mandy-Nicole |last2=Freixa |first2=Zoraida |last3=van Leeuwen |first3=Piet W. N. M. |title=Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions |journal=Chemical Society Reviews |date=2009 |volume=38 |issue=4 |pages=1099–118 |doi=10.1039/B806211K|pmid=19421583}}</ref> Such ligands are useful in the ] of ]s.<ref>{{cite journal | author = Piet W. N. M. van Leeuwen, Paul C. J. Kamer, Joost N. H. Reek, and Peter Dierkes | title = Ligand Bite Angle Effects in Metal-catalyzed C-C Bond Formation | year = 2000 | journal = ] | volume = 100 | issue = 8| pages = 2741–2769 | doi = 10.1021/cr9902704 | pmid=11749304}}</ref> Illustrative of its wide bite angle, it forms both cis and trans adducts of ]. In the latter context, xantphos is classified as a ]. A related bidentate ligand with a greater bite angle is ]. |
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The ligand is prepared by double ] of 9,9-dimethylxanthene with ] followed by treatment with ].<ref>{{cite journal | author = Mirko Kranenburg, Yuri E. M. van der Burgt, Paul C. J. Kamer, Piet W. N. M. van Leeuwen, Kees Goubitz, and Jan Fraanje | title = New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle | year = 1995 | journal = ] | volume = 14 | issue = 6| pages = 3081–3089 | doi = 10.1021/om00006a057| s2cid = 53053952 | url = https://pure.uva.nl/ws/files/2969936/882_9954y.pdf}}</ref> |
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==References== |
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<references/> |
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