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666564

Sigma-Aldrich

N-XantPhos

97%

Synonym(s):

NiXantphos, 4,6-Bis(diphenylphosphino)-10H-phenoxazine, 4,6-Bis(diphenylphosphino)phenoxazine

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About This Item

Linear Formula:
(C6H3)2NHO(P(C6H5)2)2
CAS Number:
261733-18-0
Molecular Weight:
551.55
MDL number:
MFCD03788937
UNSPSC Code:
12352005
PubChem Substance ID:
24884806
NACRES:
NA.22

Assay

97%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

mp

256-262 °C

functional group

phosphine

storage temp.

2-8°C

SMILES string

N1c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c1cccc5P(c6ccccc6)c7ccccc7

InChI

1S/C36H27NOP2/c1-5-15-27(16-6-1)39(28-17-7-2-8-18-28)33-25-13-23-31-35(33)38-36-32(37-31)24-14-26-34(36)40(29-19-9-3-10-20-29)30-21-11-4-12-22-30/h1-26,37H

InChI key

HSWZLYXRAOXOLL-UHFFFAOYSA-N

Related Categories

Application

N-XantPhos is a deprotonatable chelating aryldiphosphine ligand that can be used in:
  • The preparation of Pd-NiXantphos catalyst system for the room temperature cross-coupling reactions of unactivated aryl chlorides.
  • The synthesis of cinchonine iridium(III) cyclometalated complex that exhibits luminescence and good quantum efficiency.
  • N-XantPhos and N-modified counterparts are also used in the preparation of rhodium based catalysts for hydroformylation reaction.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A new approach to dendritic supported NIXANTPHOS-based hydroformylation catalysts.
Ricken S, et al.
J. Mol. Catal. A: Chem., 257(1-2), 78-88 (2006)
NiXantphos: A Deprotonatable Ligand for Room-Temperature Palladium-Catalyzed Cross-Couplings of Aryl Chlorides.
Zhang J, et al.
Journal of the American Chemical Society, 136(17), 6276-6287 (2014)
Enhanced emission and analyte sensing by cinchonine iridium (III) cyclometalated complexes bearing bent diphosphine chelators.
Luo S X, et al.
Organometallics, 32(10), 2908-2917 (2013)

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