18789-78-1

Basic information

• Product Name: Phosphinic acid, diphenyl-, trimethylsilyl ester
• CAS NO: 18789-78-1
• Molecular Formula: C15H19O2PSi
• Molecular Weight: 290.374
• Mol File: 18789-78-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Phosphinic acid, diphenyl-, trimethylsilyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphinic acid, diphenyl-, trimethylsilyl ester(18789-78-1)
• EPA Substance Registry System: Phosphinic acid, diphenyl-, trimethylsilyl ester(18789-78-1)

Safety Data

• Hazardous Substances Data: 18789-78-1(Hazardous Substances Data)

Usage

General Description

Phosphinic acid, diphenyl-, trimethylsilyl ester is a chemical compound with the formula (C6H5)2P(OSi(CH3)3). It is a derivative of phosphinic acid, a phosphorus-containing compound. The trimethylsilyl ester group is attached to the phosphorus atom, making it more stable and less reactive than the parent phosphinic acid. Phosphinic acid, diphenyl-, trimethylsilyl ester is used as a reagent in organic synthesis, particularly in the synthesis of phosphorus-containing compounds and in the preparation of organophosphorus pesticides. Its trimethylsilyl ester moiety makes it easier to handle and store compared to the parent acid, and it can be used as a source of phosphinic acid in various chemical reactions.

Upstream product

• 861906-61-8 4-heptylbenzyl diphenylphosphinate 
• 77152-10-4 trimethyl[(1-isopropylpropenyl)oxy]silane 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 2857-97-8 trimethylsilyl bromide 
• 53772-44-4 benzyloxydiphenylphosphine 
• 14655-53-9 allyloxy-diphenylphosphane 
• 719-80-2 Ethyl diphenylphosphinite 
• 16029-98-4 trimethylsilyl iodide 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 1079-66-9 chloro-diphenylphosphine 
• 829-85-6 diphenylphosphane 
• 1499-21-4 Diphenylphosphinic chloride 
• 762-72-1 allyl-trimethyl-silane 
• 861906-64-1 methyl 4-(((diphenylphosphoryl)oxy)methyl)benzoate 

Downstream Products

• 22214-04-6 sodium diphenylphosphinate 
• 39864-62-5 acide diphenylphosphinique lithie 
• 124340-38-1 diphenylphosphinic acid triethylsilyl ester 
• 1707-03-5 diphenyl-phosphinic acid 
• 126709-45-3 C₂₇H₂₄O₂P₂ 
• 126709-36-2 C₂₇H₂₄O₂P₂ 
• 125722-48-7 triphenylsilyldiphenylphosphinate 

Relevant articles and documents

Studies on the efficient generation of phosphorus-carbon bonds via a rearrangement of PIII esters catalysed by trimethylhalosilanes

Halotrimethylsilanes Me3SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R′R″P-OR into the corresponding phosphoryl systems R′R″P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by 31P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno PIII structures R′R″PX and silyl ethers ROSiMe3 and that they subsequently react to give the corresponding phosphorus silyl esters - Me 3SiOPR′R″-and alkyl halides RX. At higher temperatures these intermediates then react to form R′R″P(P)R compounds. This paper also features the surprising observation that when esters Ph 2POR and halotrimethylsilanes Me3SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph2R2P+X - and trimethylsilyl diphenylphosphinate - Ph2P(O) OSiMe3 - are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me3SiCl is not reactive and this paper explains why.

Esters of (Hydroxymethyl)diorganylsilanes: Synthesis and Thermally Induced Rearrangement

Twenty silanes of the type R1R2Si(H)CH3OR3 (A) were synthesized 1,R2 = Me, Ph, 1-naphthyl, PhCH2, Me3SiCH2; OR3 = OC(O)Me, OC(O)CF3, OS(O)CF3, OP(O)Ph2, OC(O)Cl> and studied for their thermal behaviour.The silanes A undergo a thermally induced rearrangement to give the corresponding silanes R1R2Si(OR3)Me (B).For compounds with OR3 = OC(O)Cl, an additional decarboxylation takes place to yield the chlorosilanes R1R2Si(Cl)Me.Except for the derivatives with OR3 = OC(O)Cl, the energetic (reaction enthalpy) and kinetic data (reaction order, frequency factor, enthalpy and entropy of activation) of these reactions were studied by means of differential scanning calorimetry (DSC).In addition the kinetics of all reactions were investigated by 1H-NMR spectroscopy.The transition state of the rearrangement was investigated by an ab initio study based on the model compound H3SiCH2OC(O)H MeH2SiOC(O)H>.The theoretical data and the experimentally obtained energetic and kinetic data are discussed in terms of mechanistic aspects of the rearrangement reaction A -> B.

SILYLPEROXIDES AS SELECTIVE OXYGENATION REAGENTS IN PHOSPHORUS CHEMISRTY

Bis(trimethylsilyl)peroxide (BSPO) can be used for chemo- and stereoselective generation of P=O group by oxygenation of P(III) centre and transformation of P=S and P=Se groups.