185509-36-8

Basic information

• Product Name: Phosphinous acid, diphenyl-, 2,4-bis(1,1-dimethylethyl)phenyl ester
• CAS NO: 185509-36-8
• Molecular Formula: C26H31OP
• Molecular Weight: 390.505
• Mol File: 185509-36-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phosphinous acid, diphenyl-, 2,4-bis(1,1-dimethylethyl)phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphinous acid, diphenyl-, 2,4-bis(1,1-dimethylethyl)phenyl ester(185509-36-8)
• EPA Substance Registry System: Phosphinous acid, diphenyl-, 2,4-bis(1,1-dimethylethyl)phenyl ester(185509-36-8)

Safety Data

• Hazardous Substances Data: 185509-36-8(Hazardous Substances Data)

Upstream product

• 96-76-4 2,4-di-tert-Butylphenol 
• 1079-66-9 chloro-diphenylphosphine 
• 20834-61-1 2-bromo-4,6-di-tert-butylphenol 

Downstream Products

• 433978-21-3 trans-[PdCl₂(PPh₂(OC₆H₃-2,4-(t)Bu₂))2] 
• 334684-33-2 [(Pd(μ-Cl)(κ2-P,C-PPh2(OC6H2-2,4-(t)Bu2)))2] 

Relevant articles and documents

Orthopalladated phosphinite complexes as high-activity catalysts for the suzuki reaction

The synthesis of a range of phosphinite ligands PR2(OAr) (R = Ph, iPr), their simple complexes with palladium(II) and their palladacyclic complexes has been investigated. The crystal structure of one of the palladacyclic complexes, [{Pd(μ2-Cl)} {κ2-P, C-PiPr2(OC6H2-2,4-t Bu2)} 2], has been determined. The palladacyclic complexes show extremely high activity in the Suzuki coupling of aryl bromide substrates with phenylboronic acid and can also be used with alkylboronic acid substrates. A comparison of the phosphinite-based catalysts with equivalent phosphite- and phosphine-based systems highlights their superior activity. The orthometallation of the phosphinite ligand in the pre-catalyst appears to be crucial for optimal activity. While the phosphinite palladacycles are only moderately active in the coupling of activated and non-activated aryl chloride substrates, their tricyclohexylphosphine adducts prove to be highly active in the coupling of the deactivated substrate, 4-chloroanisole. This high activity compared with other palladacyclic systems is explained in terms of catalyst longevity. The orthometallated precatalysts appear to undergo a reductive activation process to generate zerovalent active catalysts via reductive elimination of the orthometallated ring with a phenyl introduced by the boronic acid. This implies that the true active catalysts contain 2-arylated ligands. Catalysts formed with such 2-arylated ligands tend to show markedly higher activity than their parent ligands.

P/O ligand systems: Synthesis, reactivity, structure of tertiary o-phosphanylphenol derivatives

Reactions of C,O-dilithium reagents 1 (M = M′ = Li) or C,O-lithium-sodium reagents 1 (M = Li, M′ = Na) with chlorophosphanes afford C,O-disubstitution products 2 or phosphanylphenolates 3 which are treated subsequently with ClSiMe3 to give 4-me