CAS 787618-22-8 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

Synonyms

AX8074362; MFCD06798294 (95%); X3474RY19E; CTK8B4848; ANW-46517; 2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I-PROPOXY-1,1'-BIPHENYL; RW2258; dicyclohexyl-[2-(2,6-diisopropoxyphenyl)phenyl]phosphane; AC-28790; Dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine;

IUPAC Name

dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane;

Molecular Weight

466.646g/mol

Molecular Formula

C30H43O2P;

Canonical SMILES

CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;

InChI

InChI=1S/C30H43O2P/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25/h11-13,18-25H,5-10,14-17H2,1-4H3;

InChI Key

MXFYYFVVIIWKFE-UHFFFAOYSA-N;

Complexity

516

Covalently-Bonded Unit Count

EC Number

616-653-5

Exact Mass

466.3g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

466.3g/mol

Rotatable Bond Count

Topological Polar Surface Area

18.5A^2

UNII

X3474RY19E

Application

2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl serves a vital role as a ligand in facilitating various palladium-catalyzed coupling reactions. It is instrumental in the Suzuki reaction by enabling the efficient coupling of alkyl boronates. This versatile ligand is not only used for Pd-catalyzed couplings of secondary arylamines and alkylamines but is also crucial in Negishi cross-coupling reactions of (hetero)aryl chlorides. It's utilized in synthesizing ladder-type π-conjugated heteroacenes through double N-arylation and intramolecular O-arylation, as well as in the regiospecific synthesis of N-aryl benzimidazoles. The ligand's effectiveness extends to C-N coupling reactions at low temperatures and the Suzuki-Miyaura coupling of aryl chlorides with NHC-boranes. Moreover, it is employed in the palladium-catalyzed trifluoromethylation of hindered aryl chlorides and proves valuable in the cross-coupling of aminoethyltrifluoroborates with electron-poor aryl bromides.

February 8, 2025

Outstanding Ligand for Pd-Catalyzed Reactions

I've used Alfa Chemistry's 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl in Suzuki reactions, and it's a game-changer. Exceptional performance in Pd-catalyzed coupling, making complex syntheses smooth and efficient in our lab. Highly recommend for research applications!