CAS 1636-14-2 Bis(diethylamino)phenylphosphine

Synonyms

Phenylphosphonous tetraethyldiamide; Phosphonous diamide,N,N,N',N'-tetraethyl-P-phenyl-; Phenylbis(diethylamino)phosphine; TC-167706; SCHEMBL2226790; N-[diethylamino(phenyl)phosphanyl]-N-ethylethanamine; Bis(diethylamino)phenylphosphine, 97%; AC1L39YI; ACMC-20almr; ZINC404189;

IUPAC Name

N-[diethylamino(phenyl)phosphanyl]-N-ethylethanamine;

Molecular Weight

252.342g/mol

Molecular Formula

C14H25N2P;

Canonical SMILES

CCN(CC)P(C1=CC=CC=C1)N(CC)CC;

InChI

InChI=1S/C14H25N2P/c1-5-15(6-2)17(16(7-3)8-4)14-12-10-9-11-13-14/h9-13H,5-8H2,1-4H3;

InChI Key

HTIVDCMRYKVNJC-UHFFFAOYSA-N;

Complexity

173

Covalently-Bonded Unit Count

Exact Mass

252.176g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

252.176g/mol

NSC Number

244337

Rotatable Bond Count

Topological Polar Surface Area

6.5A^2

Application

Bis(diethylamino)phenylphosphine serves as a versatile agent in various chemical reactions, fulfilling multiple roles to enhance the efficacy and specificity of these processes. It functions as an electron-withdrawing cocatalyst in rhodium-catalyzed hydroformylation reactions, thereby facilitating the transformation of alkenes to aldehydes. Additionally, it acts as a ligand precatalyst for Heck coupling reactions, contributing to the formation of carbon-carbon bonds. Furthermore, it is utilized as a reactant for the preparation of palladium chiral P-N ligand complexes, which are essential for regio- and stereoselective dimerization reactions. This compound is also involved in the synthesis of palladium tautomeric ferrocenylphosphinites, serving as catalysts for Suzuki-Miyaura coupling, an important reaction for forming biaryl structures. Lastly, the compound promotes the Michaelis-Arbuzov rearrangement of phosphinites and phosphites in the presence of trimethylsilyl halides, highlighting its role in organophosphorus chemistry.

February 8, 2025

Excellent Cocatalyst for Advanced Catalysis Research

Using Bis(diethylamino)phenylphosphine from Alfa Chemistry significantly boosted our rhodium-catalyzed hydroformylation experiments. Its role as a ligand precatalyst was crucial for successful Heck coupling reactions. Recommended for efficient synthesis applications in industrial research settings.