4023-49-8

Usage

InChI:InChI=1/C6H9N2P/c7-3-1-5-9-6-2-4-8/h9H,1-2,5-6H2

Upstream product

• 107-13-1 acrylonitrile 
• 75-05-8 acetonitrile 

Downstream Products

• 5964-09-0 bis(2-cyanoethyl)phosphine 
• 29623-83-4 bis(2-cyanoethyl)phosphinic acid 
• 76699-53-1 Cyclohexyl-bis-<2-cyan-ethyl>-phosphin 
• 88613-75-6 Phenylmercapto-bis-<2-cyan-aethyl>-phosphinoxid 
• 4023-53-4 tris(2-cyanoethyl)phosphine 
• 91958-91-7 p-Tolylmercapto-bis-(2-cyanoaethyl)-phosphinoxyd 
• 91762-57-1 N-(4-chlorophenyl)-1,1-bis(2-cyanoethyl)phosphanecarboxamide 
• 97380-17-1 β-Phenethyl-bis-(2-cyan-ethyl)-phosphin 

Relevant academic research and scientific papers

Platinum(0)-catalysed Hydrophosphination of Acrylonitrile

The tris(cyanoethyl)phosphine complex 3> catalyses the addition of PH3 or PH(CH2CH2CN)2 to CH2=CHCN to give P(CH2CH2CN)3.

Self-replication of tris(cyanoethyl)phosphine catalysed by platinum group metal complexes

The platinum(0) complex [Pt(tcep)3], tcep = P(CH2CH2CN)3, catalyses the formation of tcep from PH3 and CH2=CHCN. The complexes [M(tcep)3] (M = Pt, Pd or Ni) and [MCl(tcep)3] (M = Rh or Ir) are compared for their catalysis of the reaction of PH(CH2CH2CN)2 with CH2=CHCN to give tcep and it is shown that the platinum(0) complex is the most efficient. The platinum(0) catalysis has been studied in detail, monitoring the kinetics by 31P-{1H} NMR spectroscopy. It is revealed that the kinetics are a complex function of the concentration of product tcep. Qualitatively, the rates also depend on [CH2=CHCN] and [catalyst]. Both 31P-{1H} and 195Pt-{1H} NMR spectroscopy suggests that addition of CH2=CHCN to [Pt(tcep)3] gives the complex [Pt(tcep)2(η2-CH2=CHCN)] which undergoes phosphine exchange on the NMR time-scale. The binuclear complex [Pt2H2(tcep)2{η-P(CH2CH 2CN)2}2], formed upon addition of PH(CH2CH2CN)2 to trans-[PtHCl(tcep)2] in the presence of base, is shown to be a catalyst precursor for the reaction of PH(CH2CH2CN)2 with CH2=CHCN. Two parallel mechanisms involving mononuclear and binuclear intermediates are discussed to rationalise these observations.

Method of producing a bis(2-carboxyethyl)alkyl phosphine oxide and a derivative thereof

A method of producing a bis(2-carboxyethyl)-alkyl phosphine oxide represented by the following general formula (1) is disclosed. STR1 The method comprises the following Steps 1-4: step 1 wherein phosphine is reacted with acrylonitrile to produce bis(2-cyanoethyl)phosphine and then, in step 2, reacted with an alkene to produce a bis(2-cyanoethyl)alkyl phosphine, and in step 3, reacted with an oxidizing agent to produce a bis(2-cyanoethyl)alkyl phosphine oxide, and in step 4, said bis(2-cyanoethyl)alkyl phosphine oxide is reacted with water or a lower alcohol to give a bis(2-carboxyethyl)alkyl phosphine oxide or a derivative thereof.

Dual Radical/Polar Pudovik Reaction: Application Field of New Activation Methods

The Pudovik reaction (addition of organophosphorus compounds containing a labile P-H bond with alkenes and alkynes) can progess via a radical or (and) ionic mechanism. A comparative and systematic study including various reagents and different activation methods (heating, photochemical or ultrasonic irradiation, and dry medium supported reactions) is presented. Photolysis is the most efficient method for the radical processes, but in a few examples, ultrasonic irradiation can be more appropriate since the reaction time is shorter and ultrasound did not induce side-reactions (in particular Z/E isomerization). Dry medium process on basic solid support is the best anionic activation (yield, time, selectivity, purification facilities). Ultrasound, by its mechanical effects, can contribute to increase yield compared to the classical thermal method under these basic conditions. All the activation methods are efficient whatever the unsaturated substrates for the phosphine reactivity, whereas the appropriate activation method is exclusively determined by the nature of the unsaturated system for the thiophosphine (or phosphine oxide) reactivity.

Alkylation of phosphine PH3 generated from red phosphorus

The generation of phosphine PH3 by alkaline hydrolysis of red phosphorus is realized. The subsequent alkylation of PH3 by terminal alkenes and alkynes in basic media leading to the corresponding aliphatic and vinylic phosphine derivatives can occur by two-steps or one-pot reaction by a Michael-like reaction mechanism.