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666564

N-XantPhos

Name: <I>N</I>-XantPhos
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24884806

UNSPSC Code:

12352005

MDL number:

MFCD03788937

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Properties

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

Description

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

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)

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)

Global Trade Item Number

SKU	GTIN
666564-500MG	04061833473993
666564-1G	04061826699782