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

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

Uses

Used in Organic Synthesis:
Phosphinic acid, diphenyl-, trimethylsilyl ester is used as a reagent in organic synthesis for the preparation of phosphorus-containing compounds. Its trimethylsilyl ester moiety facilitates easier handling and storage, making it a preferred choice for various chemical reactions.
Used in Pesticide Production:
In the agricultural industry, Phosphinic acid, diphenyl-, trimethylsilyl ester is used as a key intermediate in the synthesis of organophosphorus pesticides. Its unique properties contribute to the development of effective and targeted pest control solutions.
Used in Chemical Research:
Phosphinic acid, diphenyl-, trimethylsilyl ester serves as a valuable compound in chemical research, particularly in the study of phosphorus chemistry and the development of new applications for phosphorus-containing compounds. Its stability and reactivity make it an ideal candidate for exploring novel reactions and synthesis pathways.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1707-03-5 diphenyl-phosphinic acid 
• 125722-48-7 triphenylsilyldiphenylphosphinate 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 3385-94-2 hexamethyldisilathiane 
• 861906-61-8 4-heptylbenzyl diphenylphosphinate 
• 18187-39-8 1-chloro-3-trimethylsilylpropene 
• 861906-64-1 methyl 4-(((diphenylphosphoryl)oxy)methyl)benzoate 
• 18293-99-7 Prenyltrimethylsilane 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 77152-10-4 trimethyl[(1-isopropylpropenyl)oxy]silane 
• 762-72-1 allyl-trimethyl-silane 
• 2857-97-8 trimethylsilyl bromide 
• 53772-44-4 benzyloxydiphenylphosphine 

Downstream Products

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

Trimethylsilyl triflate mediated new carbon-carbon bond forming reactions between benzyl diphenylphosphinates and organosilicon compounds

The trimethylsilyl triflate mediated reaction of benzyl diphenylphosphinate with allyltrimethylsilane or trimethylsilyl enolate afforded the corresponding cross-coupling products in good yields. Copyright

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.

OPTICALLY ACTIVE SILYL ESTERS OF PHOSPHOROUS. II. STEREOCHEMISTRY OF REACTIONS WITH NUCLEOPHILES

We report the stereochemistry of reactions of various nucleophiles with optically active silyl esters of phosphorus of general formula: tBuPhP(X)OSiMePhNp X= -(1), Oxygen (2), Sulfur (3), Selenium (4).The list of nucleophiles includes O,S,N,C nucleophiles as well as halides.The nucleophilic attack is essentially directed towards silicon.The phosphinuos and phosphonic acid esters react with predominant retention of configuration at silicon atom, whereas the thiono and seleno crossover is explained in terms of possible interaction of the electrophilic part of the nucleophile with the oxyphosphoryl group or tricoordinate phosphorous.

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.