16610-80-3

Basic information

• Product Name: Α-PHENYLCINNAMONITRILE
• Synonyms: Α-PHENYLCINNAMONITRILE;(E)-2,3-Diphenylacrylonitrile;(E)-2,3-Diphenylpropenenitrile;[E]-2,3-Diphenylacrylonitrile;(E)-2,3-diphenylprop-2-enenitrile
• CAS NO: 16610-80-3
• Molecular Formula: C₁₅H₁₁N
• Molecular Weight: 205.26
• Mol File: 16610-80-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 48-48.5 °C
• Boiling Point: 148-156 °C(Press: 0.035 Torr)
• Appearance: /
• Density: 1.104±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Α-PHENYLCINNAMONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: Α-PHENYLCINNAMONITRILE(16610-80-3)
• EPA Substance Registry System: Α-PHENYLCINNAMONITRILE(16610-80-3)

Safety Data

• Hazardous Substances Data: 16610-80-3(Hazardous Substances Data)

Upstream product

• 6114-57-4 (Z)-2,3-diphenylacrylonitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 501-65-5 diphenyl acetylene 
• 140-29-4 phenylacetonitrile 
• 100-52-7 benzaldehyde 
• 98-87-3 benzylidene dichloride 
• 100-44-7 benzyl chloride 
• 22711-21-3 4-methoxybenzil 
• 15146-07-3 meso-1,2-dicyano-1,2-diphenylethane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 557-21-1 zinc(II) cyanide 
• 141-52-6 sodium ethanolate 
• 14377-99-2 1,2,3-triphenyl-1,3-propanedicarbonitrile 
• 110-89-4 piperidine 

Downstream Products

• 96272-62-7 5-oxo-2,3,4,5-tetraphenyl-valeronitrile 
• 873973-22-9 2-ethyl-2,3-diphenyl-valeronitrile 
• 40232-60-8 2,3-diphenyl-valeronitrile 
• 15146-07-3 meso-1,2-dicyano-1,2-diphenylethane 
• 5424-86-2 (+/-)-1,2-dicyano-1,2-diphenylethane 
• 4023-77-2 1-benzoyl-1,2-diphenylethylene 
• 5350-66-3 2,3,3-triphenyl-propionitrile 
• 7435-32-7 2-benzhydryl-2-phenyl-butyronitrile 
• 2900-70-1 2,3-bis-(4-nitro-phenyl)-acrylonitrile 
• 6114-57-4 (Z)-2,3-diphenylacrylonitrile 
• 53983-69-0 2,3-dibromo-2,3-diphenyl-propionitrile 
• 5415-80-5 2,3-diphenylpropan-1-amine 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 98011-35-9 4-Amino-5,6-diphenyl-2-thioxo-1,2,5,6-tetrahydropyrimidine 

Relevant articles and documents

Nickel(0) Catalysed Additions of Hydrogen Cyanide to Alkynes: Stereochemistry, Mechanism, and Preparative Application

The addition of hydrogen cyanide to both terminal and disubstituted acetylenes occurs with cis-stereospecificity in moderate to excellent yields when catalysed by a nickel(0) complex.

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.