20580-36-3

Upstream product

• 67-56-1 methanol 
• 5930-72-3 dimethyl thiophosphite 
• 124-41-4 sodium methylate 
• 107-13-1 acrylonitrile 
• 96-36-6 methyl phosphite 
• 868-85-9 Dimethyl phosphite 
• 74-85-1 ethene 
• 7677-24-9 trimethylsilyl cyanide 
• 161186-13-6 Dimethyl (Z)-(2-cyano-1-vinyl)phosphonate 

Downstream Products

• 2526-69-4 dimethyl (2-carbaminoethyl)phosphonate 

Relevant academic research and scientific papers

Beta-cyano phosphoryl derivatives as well as preparation method and application thereof

The invention discloses Beta-cyano phosphoryl derivatives as well as a preparation method and an application thereof. Alkene is used as an initiator, and raw materials are easy to obtain and wide in type; products prepared with the method are diversified in type and wide in application range, can be directly used and can be used for synthesizing organic phosphine flame retardants, drugs and extracting agents. Besides, the method adopts simple steps, has mild reaction conditions, causes low pollution and is suitable for industrial production, the yield of target products is high, and reaction operation and after-treatment process are simple.

Me3P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts

Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes

PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78-85%) in all cases. The protocol was also extended with good results to α,β-unsaturated esters and nitriles. This demonstrates that PS-BEMP is a good catalyst for the phospha-Michael addition to electron-poor alkenes.

Reduction of activated conjugated alkenes by the InCl3-NaBH 4 reagent system

A combination of a catalytic amount of indium (III) chloride and sodium borohydride in acetonitrile reduces selectively the carbon-carbon double bonds in conjugated alkenes such as α,α-dicyano olefins, α,β-unsaturated nitriles, cyanoesters, cyanophosphonate and dicarboxylic esters. However, reduction of chalcones is little different. They are reduced to a mixture of saturated ketones and alcohols if the reaction mixture is quenched with H2O, whereas quenching with MeOH leads to saturated alcohols only.

Use of indium hydride (Cl2InH) for chemoselective reduction of the carbon-carbon double bond in conjugated alkenes

Indium hydride (Cl2InH) generated in situ from a combination of a catalytic amount of indium(III) chloride and sodium borohydride selectively reduces the carbon-carbon double bond in conjugated alkenes such as α,α-dicyano olefins, α,β-unsaturated nitriles, cyano esters, cyanophosphonate, diesters and ketones.