4023-49-8

Basic information

• Product Name: BIS(2-CYANOETHYL)PHOSPHINE
• Synonyms: AURORA KA-1108;BIS(2-CYANOETHYL)PHOSPHINE;3-(2-Cyano-ethylphosphanyl)-propionitrile;3,3’-phosphinidenebis-propanenitril;3,3'-Phosphinidenebis(propiononitrile);Propanenitrile, 3,3'-phosphinidenebis-;3-(2-cyanoethylphosphanyl)propanenitrile;3-(2-cyanoethylphosphino)propionitrile
• CAS NO: 4023-49-8
• Molecular Formula: C₆H₉N₂P
• Molecular Weight: 140.12
• EINECS: 223-686-5
• Product Categories: Secondary Phosphines
• Mol File: 4023-49-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 327.8 °C at 760 mmHg
• Flash Point: 152.1 °C
• Appearance: /
• Vapor Pressure: 0.000197mmHg at 25°C
• CAS DataBase Reference: BIS(2-CYANOETHYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2-CYANOETHYL)PHOSPHINE(4023-49-8)
• EPA Substance Registry System: BIS(2-CYANOETHYL)PHOSPHINE(4023-49-8)

Safety Data

• Hazardous Substances Data: 4023-49-8(Hazardous Substances Data)

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

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

Relevant articles and documents

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.

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.