CAS 161265-03-8 (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

Synonyms

TRA0068476; Xanthene, 4,5-bis(diphenylphosphino)-9,9-dimethyl-; 4,5-bis(diphenylphosphino)-9,9-dimethlxanthene; FT-0645040; 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene; BP-12287; 30244-EP2280001A1; Y-200029; KSC485M5J; 9,9-dimethyl-4,5-bis(diphenyl phosphino)xanthene;

IUPAC Name

(5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane;

Molecular Weight

578.632g/mol

Molecular Formula

C39H32OP2;

Canonical SMILES

CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C;

InChI

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;

InChI Key

CXNIUSPIQKWYAI-UHFFFAOYSA-N;

Storage

Room temperature.

Complexity

731

Covalently-Bonded Unit Count

Exact Mass

578.193g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

578.193g/mol

Rotatable Bond Count

Topological Polar Surface Area

9.2A^2

UNII

NMU72MOG9B

Application

(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) is an organophosphorus compound that serves as a versatile bidentate ligand, primarily valued for its wide bite angle. This characteristic enhances its function in a myriad of catalytic reactions. It has proven to be highly effective in the hydroformylation of alkenes and is prominently used in a variety of other transformations, including the Suzuki reaction and intermolecular couplings, such as those involving amides and hydrazones with aryl halides. Its applications extend to the coupling of heteroarylamines with aryl halides, hydrophosphinylation of alkenes and alkynes, as well as serving as a catalyst in Au(I)-catalyzed dehydrogenative silation of alcohols, sulfinylation of aryl iodides, and Pd-catalyzed carbonylation reactions. Additionally, it facilitates complex reactions, like the Ni-catalyzed alkynylcyanation of alkynes and Pd-catalyzed N-arylation of pyrazoles, while also accommodating processes like dehydrogenation borylation, one-pot synthesis of triazoles, and Cu-catalyzed arylation techniques. This compound is instrumental in furthering a host of synthetic methodologies, ranging from ene-type reactions and oxidative synthesis to complex borylation processes, thereby showcasing its indispensable role in advanced organic chemistry.

December 13, 2024

Effective Ligand for Versatile Catalytic Applications

I used (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) in Pd- and Rh-catalyzed reactions. Its wide bite angle enhances selectivity and efficiency, perfect for hydroformylation and Suzuki reactions. Highly recommend for chemical research!