CAS 261733-18-0 N-XantPhos - Catalysts / Alfa Chemistry

Synonyms

Bis(diphenylphosphino)phenoxazine; DTXSID70390703; TRA0045396; 4,6-bis(diphenylphosphino)-phenoxazine; N-XantPhos, 97%; BB0294709; B2717; 4,6-Bis(diphenylphosphino)phenoxazine; 10H-Phenoxazine, 4,6-bis(diphenylphosphino)-; DB-009532;

IUPAC Name

(6-diphenylphosphanyl-10H-phenoxazin-4-yl)-diphenylphosphane;

Molecular Weight

551.566g/mol

Molecular Formula

C36H27NOP2;

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC4=C3OC5=C(N4)C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7;

InChI

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;

Complexity

671

Covalently-Bonded Unit Count

Exact Mass

551.157g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

551.157g/mol

Rotatable Bond Count

Topological Polar Surface Area

21.3A^2

Application

N-XantPhos is a versatile chelating aryldiphosphine ligand, primarily used as a deprotonatable component in advanced catalytic processes. Its applications span the preparation of the Pd-NiXantphos catalyst system, enabling efficient room-temperature cross-coupling of unactivated aryl chlorides, to the synthesis of cinchonine iridium(III) cyclometalated complexes known for their luminescence and high quantum efficiency. Furthermore, N-XantPhos and its modified versions are instrumental in formulating rhodium-based catalysts for hydroformylation reactions, showcasing high selectivity. This ligand's role extends into various industries, where it serves as an intermediate in pharmaceuticals, agrochemicals, dyestuffs, and fine chemical production, underscoring its importance in both medical and material synthesis.

February 3, 2025

Reliable Ligand for Efficient Catalysis

N-XantPhos proved invaluable in our research, enhancing Pd catalysis for aryl chloride coupling. Its performance in synthesizing luminescent complexes was impressive, showcasing high efficiency and selectivity. Highly recommend for academic and industrial applications.