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Details

Stereochemistry ACHIRAL
Molecular Formula C39H32OP2
Molecular Weight 578.6183
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XANTPHOS

SMILES

CC1(C)C2=CC=CC(P(C3=CC=CC=C3)C4=CC=CC=C4)=C2OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7

InChI

InChIKey=CXNIUSPIQKWYAI-UHFFFAOYSA-N
InChI=1S/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

HIDE SMILES / InChI

Molecular Formula C39H32OP2
Molecular Weight 578.6183
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Unraveling the origin of regioselectivity in rhodium diphosphine catalyzed hydroformylation. A DFT QM/MM study.
2001 Aug 8
An X-ray study of the effect of the bite angle of chelating ligands on the geometry of palladium(allyl) complexes: implications for the regioselectivity in the allylic alkylation.
2001 Jul 2
Wide bite angle diphosphines: xantphos ligands in transition metal complexes and catalysis.
2001 Nov
Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl iodides and arenesulfinates.
2002 Dec 26
Pd-catalyzed intermolecular amidation of aryl halides: the discovery that xantphos can be trans-chelating in a palladium complex.
2002 May 29
Pd-catalyzed N-arylation of heteroarylamines.
2002 Oct 3
Development for an efficient synthesis method of 2'-deoxyguanosine-C8 adducts with several amino/nitro-arenes.
2003
Amines made easily: a highly selective hydroaminomethylation of olefins.
2003 Aug 27
Palladium-catalyzed amination of aryl nonaflates.
2003 Dec 12
Alcoholysis of acylpalladium(II) complexes relevant to the alternating copolymerization of ethene and carbon monoxide and the alkoxycarbonylation of alkenes: the importance of Cis-coordinating phosphines.
2003 May 7
Polar phase hydroformylation: the dramatic effect of water on mono- and dirhodium catalysts.
2003 Sep 17
Versatile synthesis of meso-aryloxy- and alkoxy-substituted porphyrins via palladium-catalyzed C-O cross-coupling reactions.
2003 Sep 4
Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts.
2004 Aug 20
Palladium-mediated arylation of 3-aminopiperidines and 3-aminopyrrolidines.
2004 Dec 10
General synthesis of meso-amidoporphyrins via palladium-catalyzed amidation.
2004 May 27
Synthesis of N,N-Dialkyl-N'-arylhydrazines via palladium-catalyzed N-arylation by using N,N-dialkylhydrazines/2LiCl adducts.
2005 Apr 14
Chemical synthesis of 2'-deoxyguanosine-C8 adducts with heterocyclic amines: an application to synthesis of oligonucleotides site-specifically adducted with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
2006 Jun
Pd-Xantphos-catalyzed direct arylation of nucleosides.
2006 Sep 28
Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.
2007 Apr 13
Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald-Hartwig C-N cross-coupling.
2007 Feb 15
Chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine.
2007 May 10
Conformational analysis of a helically distorted gold(I) macrocycle derived from xantphos: evidence for the aurophilic Au--Au interaction from NMR.
2007 Nov
Synthesis of new N-arylpyrimidin-2-amine derivatives using a palladium catalyst.
2008 Apr 9
Xantphos as an efficient ligand for palladium-catalyzed cross-coupling reactions of aryl bromides and triflates with allyl acetates and indium.
2008 Feb 1
4,6-Bis(diphenyl-phosphino)phenoxazine (nixantphos).
2008 Mar 14
Synthesis of Weinreb amides via Pd-catalyzed aminocarbonylation of heterocyclic-derived triflates.
2008 Mar 7
Pd-catalyzed carboetherification of beta,gamma-unsaturated oximes: a novel approach to Delta2-isoxazolines.
2008 May 1
New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: synthesis, and in vitro antimalarial activity.
2008 Oct 15
Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.
2008 Sep 19
Bite angle effects of diphosphines in C-C and C-X bond forming cross coupling reactions.
2009 Apr
Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents.
2009 Dec 3
Ruthenium xantphos complexes in hydrogen transfer processes: reactivity and mechanistic studies.
2009 Jan 28
PIKfyve regulation of endosome-linked pathways.
2009 Jul
Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols.
2009 Mar 19
Nickel-catalyzed vinylation of aryl chlorides and bromides with vinyl ZnBr.MgBrCl.
2009 May 1
Platinum-catalyzed direct amination of allylic alcohols under mild conditions: ligand and microwave effects, substrate scope, and mechanistic study.
2009 Oct 14
Pincer phosphine complexes of ruthenium: formation of Ru(P-O-P)(PPh3)HCl (P-O-P = xantphos, DPEphos, (Ph2PCH2CH2)2O) and Ru(dppf)(PPh3)HCl and characterization of cationic dioxygen, dihydrogen, dinitrogen, and arene coordinated phosphine products.
2010 Aug 16
Ligand-mediated highly effective and selective C-N coupling for synthesizing bioactive N-aryltriazole acyclonucleosides.
2010 Dec 17
Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols.
2010 Dec 21
Competitive and selective Csp3-Br versus Csp2-Br bond activation in palladium-catalysed Suzuki cross-coupling: an experimental and theoretical study of the role of phosphine ligands.
2010 Dec 3
Gold(I) halide complexes of bis(diphenylphosphine)diphenyl ether ligands: a balance of ligand strain and non-covalent interactions.
2010 Jun 14
A highly efficient palladium/copper cocatalytic system for direct arylation of heteroarenes: an unexpected effect of Cu(Xantphos)I.
2010 Mar 24
[mu-4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene]bis[(trifluoroacetato)gold(I)] and its dichloromethane 0.58-solvate.
2010 May
Dienyl homoallyl alcohols via palladium catalyzed ene-type reaction of aldehydes with 1,3-dienes.
2010 Nov 24
Oxygen gas sensing by luminescence quenching in crystals of Cu(xantphos)(phen)+ complexes.
2010 Oct 13
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:13:20 GMT 2023
Edited
by admin
on Sat Dec 16 08:13:20 GMT 2023
Record UNII
NMU72MOG9B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XANTPHOS
MI  
Common Name English
PHOSPHINE, 1,1'-(9,9-DIMETHYL-9H-XANTHENE-4,5-DIYL)BIS(1,1-DIPHENYL-
Systematic Name English
XANTPHOS [MI]
Common Name English
9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE
Systematic Name English
4,5-BIS(DIPHENYLPHOSPHINO)-9,9-DIMETHYLXANTHENE
Systematic Name English
Code System Code Type Description
CAS
161265-03-8
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY
PUBCHEM
636044
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY
WIKIPEDIA
Xantphos
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY
MERCK INDEX
m11538
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY Merck Index
FDA UNII
NMU72MOG9B
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID20348350
Created by admin on Sat Dec 16 08:13:20 GMT 2023 , Edited by admin on Sat Dec 16 08:13:20 GMT 2023
PRIMARY