6783-71-7

Basic information

• Product Name: 2-Cyanoethylphosphine
• Synonyms: 2-Cyanoethylphosphine
• CAS NO: 6783-71-7
• Molecular Formula: C₃H₆NP
• Molecular Weight: 87.06
• Product Categories: Primary Phosphines
• Mol File: 6783-71-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Cyanoethylphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanoethylphosphine(6783-71-7)
• EPA Substance Registry System: 2-Cyanoethylphosphine(6783-71-7)

Safety Data

• Hazardous Substances Data: 6783-71-7(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 91551-39-2 Cyclohexyl-<2-cyan-ethyl>-phosphin 
• 40438-65-1 Dicyclohexyl-<2-cyan-ethyl>-phosphin 
• 144150-98-1 3-(2,2-Bis-diphenylphosphanyl-ethylphosphanyl)-propionitrile 
• 144151-05-3 3-(2,2-Bis-diphenylphosphanyl-1-methyl-ethylphosphanyl)-propionitrile 

Relevant articles and documents

Regioselectivity of the photochemical addition of ammonia, phosphine, and silane to olefinic and acetylenic nitriles

An investigation of the regioselectivity and mechanisms of the photochemical addition of NH3, PH3, and SiH4 to olefinic and acetylenic nitriles is described. The photolysis of NH3 in the presence of acrylonitrile led to the α-addition product 2-aminopropanenitrile (2), propanenitrile, and 2,3-dimethylbutanedinitrile (3). When NH3 was photolyzed in the presence of substituted derivatives (crotononitrile, methacrylonitrile, or 1-cyclohexenecarbonitrile), the α-addition products were still obtained. However, under similar reaction conditions, only the β-addition products, 7 and 8, were obtained from acrylonitrile and PH3, or acrylonitrile and SiH4, respectively. On the other hand, the photolysis of 2-butynenitrile and NH3 gave the β-addition products, (Z)- and (E)-3-aminocrotononitrile (10). The photolysis of these acetylenic nitriles with PH3 or SiH4 also gave the β-adducts (12) and (13). The α-addition of NH3 proceeds by the stepwise addition of H· and ·NH2, respectively, to the α,β-unsaturated nitriles. The β-addition products are formed by a radical chain mechanism initiated by photochemically generated radicals. The radical chain pathway provides an explanation for a number of previously described photochemical additions to olefins and acetylenes. Photochemical processes similar to the addition of ammonia and phosphine to unsaturated organic compounds may have played a role in the evolution of the atmosphere of the primitive Earth, and may even be currently occurring in the atmospheres of other planets.

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.