19295-96-6

Basic information

• Product Name: Phosphonic acid, (2-phenylethenyl)-, bis(1-methylethyl) ester
• CAS NO: 19295-96-6
• Molecular Formula: C14H21O3P
• Molecular Weight: 268.293
• Mol File: 19295-96-6.mol

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, (2-phenylethenyl)-, bis(1-methylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, (2-phenylethenyl)-, bis(1-methylethyl) ester(19295-96-6)
• EPA Substance Registry System: Phosphonic acid, (2-phenylethenyl)-, bis(1-methylethyl) ester(19295-96-6)

Safety Data

• Hazardous Substances Data: 19295-96-6(Hazardous Substances Data)

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 1809-20-7 diisopropyl hydrogenphosphonate 
• 103-64-0 bromostyrene 
• 591-50-4 iodobenzene 
• 4472-27-9 diisopropyl vinylphosphonate 
• 108-86-1 bromobenzene 
• 100-42-5 styrene 
• 116-17-6 triisopropyl phosphite 
• 101349-79-5 2-phenylvinyl iodide 
• 536-74-3 phenylacetylene 
• 1660-95-3 Tetraisopropyl methylenediphosphonate 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction

We successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki-Heck reaction product) using aryl halides and dialkyl vinyl phosphonates in higher yields. The low catalyst loading, easy recovery of reaction product and 8 times catalyst recycling are the major highlights of this proposed protocol.

Preparation method of olefin phosphate compound

The invention discloses a preparation method of an olefin phosphate compound. The method comprises the following steps: arylethylene and phosphate according to a mol ratio 1:4-6 are used as raw materials; ferric chloride and copper salt are used as catalysts, and di-tert-butyl peroxide is used as an oxidizing agent; the raw materials and triethylamine are mixed, an organic solvent is added, and under the protection of inert gas, a reaction is carried out at 90-110 DEG C; after the reaction ends, washing is carried out, rotary evaporation is used for removing the solvent, and column chromatography is carried out in order to obtain the olefin phosphate compound. Base metal copper and iron are used as catalysts, reactant arylethylene and phosphate have low price, toxicity is low, the oxidizing agent is green and environmentally friendly, and the yield of the synthetic reaction of the olefin phosphate compound is high.

Mono and double Mizoroki-Heck reaction of aryl halides with dialkyl vinylphosphonates using a reusable palladium catalyst under aqueous medium

Operationally-simple and reusable Pd-catalyzed mono and double Mizoroki-Heck reactions of aryl halides and dialkyl vinylphosphonates using iPr2NH as a base in aqueous medium under air were developed. For aryl iodides, the reaction could be conducted at 80 °C under a low catalyst loading (0.1-1 mol%). When aryl bromides were applied, however, a greater amount of catalyst (5 mol%) and a longer reaction time at 120 °C were required. Simply changing dialkyl vinylphosphonates as the limiting reagent led to the formation of 2,2-diaryl vinylphosphonates in good to high yields. After reaction, the residual aqueous solution could be reused for both mono and double Mizoroki-Heck reactions, making the reactions greener and reducing wastage of precious metals and use of harmful organic solvents as the reaction medium.

Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel

The use of simple and inexpensive NiCl2?6 H2O as a catalyst precursor for C?P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. Control experiments showed the in situ formation of (RO)2P(O)H as the species that undergo the addition into the C≡C bond at the alkynes to yield the product of P?H addition. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand. This method is useful for the preparation of organophosphonates for both phenylacetylene as a terminal alkyne model and internal alkynes in yields that range from good to modest.

First reusable ligand-free palladium catalyzed C-P bond formation of aryl halides with trialkylphosphites in neat water

A reusable ligand-free palladium catalyzed phosphonation of aryl iodides, bromides and chlorides with trialkylphosphites is described for the first time in neat water. The aryl phosphonates are obtained in good to excellent yields. The reaction can be also performed with Ni(II) with longer reaction time. The role of tetrabutylammonium bromide in this reaction as reducing agent for generation of Pd(0) at room temperature is also demonstrated. Pd(0)/TBAB was easily reused for three runs without decreasing the efficiency.

Synthesis of aryl and arylmethyl phosphonates by cross-coupling of aryl or arylmethyl halides (X = I, Br and Cl) with diisopropyl H-phosphonate

An efficient and generally applicable protocol for the palladacycle- catalysed arylation or K2CO3-promoted arylmethylation of diisopropyl H-phosphonate has been developed. The remarkable features of the palladacycle-catalysed arylation reaction include wide substrate scope (aryl iodides, bromides and chlorides), significant shortening of the reaction time (2 or 3 h) and a low catalyst loading of 1 mol-%. Note that with the base K 2CO3 as promoter, arylmethylation could be achieved without any palladium catalyst. Moreover, the first example of a palladium-catalysed phosphonation of inactive electron-rich aryl chlorides with tBuOK as the base has been realized. This result could be considered an important improvement and complement to earlier work of Montchamp and Han, whose catalytic systems are typically compatible with electron-deficient and electron-neutral aryl chlorides.

Selective addition of P(O)H bonds to alkynes catalyzed by transition metals immobilized on polystyrene-bound triphenylphosphine

Addition of P(O)H bonds to alkynes catalyzed by transition metals (Rh, Pd, and Ni) immobilized on polystyrene-bound triphenylphosphine proceeded efficiently to afford high yields of the addition products with high regioselectivity. The immobilized catalys

Copper-catalyzed aerobic oxidative coupling of terminal alkynes with H-phosphonates leading to alkynylphosphonates

(Chemical Equation Presented) Copper catalyzed the aerobic oxidative coupling of terminal alkynes with H-phosphonates to afford alkynylphosphonates in high yields.