Skip to Content
Merck
CN
All Photos(2)

Documents

666564

Sigma-Aldrich

N-XantPhos

97%

Sign Into View Organizational & Contract Pricing
All Photos(2)
Synonym(s):
NiXantphos, 4,6-Bis(diphenylphosphino)-10H-phenoxazine, 4,6-Bis(diphenylphosphino)phenoxazine
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

Quality Level

100

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.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service