60763-39-5

Usage

InChI:InChI=1/C15H17O4P/c1-13(2)17-20(16,18-14-9-5-3-6-10-14)19-15-11-7-4-8-12-15/h3-13H,1-2H3

Upstream product

• 67-63-0 isopropyl alcohol 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 6921-14-8 Diphenyl potassium phosphate 
• 7228-47-9 2-(2-naphthyl)ethanol 
• 546-68-9 titanium(IV)isopropoxide 
• 681035-22-3 (2-oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester 
• 838-85-7 diphenyl hydrogen phosphate 
• 26386-88-9 diphenyl phosphoryl azide 
• 108-95-2 phenol 
• 4712-55-4 diphenyl hydrogen phosphite 

Downstream Products

• 1623-24-1 isopropylphosphoric acid 
• 25723-74-4 diphenyl(trimethylsilyl)phosphate 
• 838-85-7 diphenyl hydrogen phosphate 
• 1634-11-3 1,1-diphenyl-2-methylpropane 
• 91-01-0 1,1-Diphenylmethanol 

Relevant academic research and scientific papers

Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides

We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P?N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from the corresponding amines in excellent yields as well (8 examples, up to 96%).

Recyclable copper catalyst on chitosan for facile preparation of alkyl/aryl mixed phosphates via deaminated esterification between diphenylphosphoryl azides and aliphatic alcohols

An efficient methodology was established for the preparation of alkyl/aryl mixed phosphates under aerobic conditions promoted by a easily recoverable heterogeneous catalyst. This highly active copper catalyst was obtained by directly mixing of copper precursor with chitosan solution, followed by a simple work-up process. In this catalytic system, different phosphoryl azides and aliphatic alcohols were employed to generate desired products in moderate to excellent yields with good functional group tolerance. This protocol provided a practical application of the chitosan supported heterogeneous copper catalyst towards a novel P–O bond formation.

SN2 Reaction of Diarylmethyl Anions at Secondary Alkyl and Cycloalkyl Carbons

The substitution reaction of the diethyl allylic and propargylic phosphates with Ar2CH anions was applied to sec-alkyl phosphates to compare reactivity and stereoselectivity. However, the substitution took place on the ethyl carbon of the diethyl phosphate group. We then found that the diphenyl phosphate leaving group ((PhO)2PO2) was suited for the substitution at the sec-alkyl carbon. Enantioenriched diphenyl sec-alkyl phosphates with different substituents (Me, Et, iPr) on the vicinal position underwent the substitution reaction with almost complete inversion (>99% enantiospecificity). The substitution reactions of cyclohexyl phosphates possessing cis or trans substituents (Me and/or tBu) at the C4, C3, and C2 positions of the cyclohexane ring were also studied to observe the difference in reactivity among the cis and trans isomers. A transition-state model with the phosphate leaving group ((PhO)2PO2) in the axial position was proposed to explain the difference. This model was supported by computational calculation of the virtual substitution reaction of the structurally simpler “dimethyl” cyclohexyl phosphates (leaving group = (MeO)2PO2) with MeLi. Furthermore, the calculation unexpectedly indicated higher propensity of (PhO)2PO2 as a leaving reactivity than alkyl phosphate groups such as (MeO)2PO2 and (iPrO)2PO2.

Copper catalyzed synthesis of aryl/alkyl mixed phosphates from diphenylphosphoryl azides and aliphatic alcohols under mild conditions

An efficient and convenient one-pot protocol is developed to prepare aryl/alkyl mixed phosphates in the presence of copper catalyst under exceptionally mild conditions. A series of versatile, ubiquitous, and inexpensive phosphoryl azides and aliphatic alcohols are combined for the first time ever. Diphenylphosphoryl azide is employed as novel phosphors reagent through an unexpected cleavage of P[sbnd]N bond. The transformation is advantageous with respect to a broad of functional group compatibility and different esterification products are isolated in good to excellent results. This new catalytic system represents a superior platform towards a mild, operationally simple, practical, and scalability alternative to access target molecules. Furthermore, a plausible mechanism is proposed based on insightful mechanistic studies.

Synthesis method of copper-catalyzed phosphate mixed ester compound

The invention provides a synthesis method of a copper-catalyzed phosphate mixed ester compound. The synthesis method comprises the steps that a phosphate ester azide compound and fatty alcohol are mixed, then a copper catalyst is added, alkali is added, reaction is conducted at the temperature of 20-100 DEG C for 3-24 h, and the phosphate mixed ester compound is obtained through aftertreatment. According to the synthesis method, the phosphate ester azide compound and the fatty alcohol are adopted to synthesize the phosphate mixed ester compound for the first time, in the synthesis process, only the copper catalyst and the alkali with the catalytic dosage are needed to be added, operation is easy, the defect of needing inert gas protection is overcome, and the synthesis method is novel andefficient.

Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates

Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.

Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

The formation of H-phosphonate diesters is an important step in the synthesis of oligonucleotides. Using diphenylchlorophosphate as the activator for the coupling step is often accompanied by side reactions as a result of self 'capping' and other reactions of the reactive intermediate. In the absence of base, the activation of ethyl H-phosphonate with diphenylchlorophosphate probably occurs through the intermediate formation of bis diethyl pyro-di-H-phosphonate rather than the expected diphenyl ethyl pyro-H-phosphonate. Pyridine acts as a nucleophilic catalyst converting diphenylchlorophosphate to its pyridinium adduct. Several side and unwanted reactions are quantified so that conditions to minimise these can be identified.

Efficient and convenient one-pot synthesis of phosphoramidates and phosphates

A simple and efficient one-pot method is described for the synthesis of phosphoramidates/phosphates in excellent yields from dialkylphosphites and trichloroisocyanuric acid in acetonitrile and subsequent treatment with dialkyl amines/alcohols. The procedure is operationally simple, has reduced reaction times, and uses a one-pot procedure. Copyright Taylor & Francis Group, LLC.

P-Toluenesulfonic acid-Celite as a reagent for synthesis of esters of alkylphosphonic acids under solvent-free conditions

The coupling reaction of alkylphosphonic acids and alcohols on the surface of p-toluenesulfonic acid-Celite under mild and solvent-free conditions gave the corresponding phosphonates in excellent yields. This method provides a useful rapid synthesis of phosphonates for use in the unambiguous identification of chemical warfare agents.