CAS 213697-53-1 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Synonyms

2-di-cyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; 118492-EP2272832A1; (2'-dicyclohexylphosphanyl-biphenyl-2-yl)dimethyl-amine; 2-(Dicyclohexylphosphino)-2'-(N,N-diMethylaMino)biphenyl, 98% DavePhos; (2'-dicyclohexylphosphanyl -biphenyl-2-yl)-dimethyl-amine; Buchwald phosphine ligands, davephos phosphine ligand-; 2-dicyclohexylphosphino-2'-(N,N'-dimethylamino)biphenyl; [1,1'-BIPHENYL]-2-AMINE, 2'-(DICYCLOHEXYLPHOSPHINO)-N,N-DIMETHYL-; 2'-(dicyclohexylphosphino)-N,N-dimethyl-2-biphenylamine; RL02630;

IUPAC Name

2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline;

Molecular Weight

393.555g/mol

Molecular Formula

C26H36NP;

Canonical SMILES

CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;

InChI

InChI=1S/C26H36NP/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22/h9-12,17-22H,3-8,13-16H2,1-2H3;

InChI Key

ZEMZPXWZVTUONV-UHFFFAOYSA-N;

Complexity

433

Covalently-Bonded Unit Count

Exact Mass

393.259g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

393.259g/mol

Rotatable Bond Count

Topological Polar Surface Area

3.2A^2

UNII

9877ONU78F

Application

2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl is a versatile ligand with multiple significant applications in chemical synthesis and biomedical research. Its primary purpose is to serve as a potent inhibitor of the enzyme bromodomain, which is linked to cancer and other diseases. By covalently binding to the bromodomain, it blocks the ATP site, selectively inhibiting its function over other domains. Additionally, it acts as an effective ligand in various palladium-catalyzed reactions, such as the Suzuki coupling, C-N bond formation, and arylation of ester enolates, frequently achieving high yields at room temperature. This compound is also instrumental in promoting Pd-catalyzed N-arylation of indoles, synthesis of aryl-tert-butyl ethers, and other cross-coupling reactions. Beyond its role in synthesis, it exhibits biological activity, including binding to Toll-like receptor 4 (TLR4), a key player in cytokine signaling, and demonstrates some regulatory effects unrelated to bromodomain inhibition, such as influencing depression pathways. Overall, 2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl plays a critical role in advancing both chemical methods and therapeutic research.

December 09, 2024

Versatile Ligand for Innovative Research

Alfa Chemistry's 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl excelled as a ligand in my research. I used it for Pd-catalyzed Suzuki coupling, yielding high-purity compounds efficiently. Its application expanded our synthesis capabilities immensely.