72676-31-4

Basic information

• Product Name: (E)-3-phenylacrylonitrile-2-d
• Synonyms: (E)-3-phenylacrylonitrile-2-d
• CAS NO: 72676-31-4
• Molecular Weight: 130.153
• Mol File: 72676-31-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-3-phenylacrylonitrile-2-d(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-phenylacrylonitrile-2-d(72676-31-4)
• EPA Substance Registry System: (E)-3-phenylacrylonitrile-2-d(72676-31-4)

Safety Data

• Hazardous Substances Data: 72676-31-4(Hazardous Substances Data)

Upstream product

• 24840-05-9 (Z)-cinnamonitrile 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 100-52-7 benzaldehyde 
• 37854-15-2 2-bromo-3-phenyl-2-propenenitrile 
• 1885-38-7 cinnamic nitrile 

Relevant articles and documents

Selective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source

The selective α-deuteration of α,β-unsaturated nitriles using the strong base tBuOK or a metal-ligand cooperative Ru pincer catalyst is described. With D2O as deuterium source and glyme as solvent at 70 °C, tBuOK is an efficient catalyst for deuteration at the α-C(sp2) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the tBuOK-catalysed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein's ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst is found to be significantly higher than that of tBuOK, allowing reactions to proceed well even at room temperature. A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using tBuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D2O. (Figure presented.).

THE WITTIG-HORNER REACTION IN HETEROGENEOUS MEDIA1-X: SYNTHESIS OF α DEUTERATED FUNCTIONAL OLEFINS USING POTASSIUM CARBONATE WITH DEUTERIUM OXIDE.

α-Labelled functional olefins ( percent D >95 percent) are prepared in high yields by the WITTIG-HORNER reaction in the presence of a 6M K2CO3- deuterium oxide solution at room temperature.

VINYL CARBANIONS DERIVED FROM CIS-CINNAMONITRILE-REACTIONS WITH ELECTROPHILES AND CONFIGURATIONAL STABILITY

Vinyl carbanions derived from cis-cinnamonitrile 1 were formed by reacting it with lithium-diisopropylamide (LDA) as a base in aprotic solvents at low temperatures; reaction with various electrophiles (E) resulted in the corresponding derivatives PhCH=C(E)CN.The configurational stability of the vinyl carbanions derived from 1 and the geometry of the reaction products was effected by the solvating properties of the medium.Retention of configuration was achieved in a poor solvating medium-diethyl ether-hexane (4:1).Addition of a crown ether or using THF as a solvent resulted in products having trans geometry.The site of deprotonation of cinnamonitrile (cis and trans) was compared to that of cinnamic esters and discussed.Determination of the geometry of the products was based on their 1H NMR spectra.