61469-71-4

Basic information

• Product Name: 4-(2-cyano-phenylethenyl)benzonitrile
• Synonyms: 4-(2-cyano-phenylethenyl)benzonitrile
• CAS NO: 61469-71-4
• Molecular Formula: C₁₆H₁₀N₂
• Molecular Weight: 230.264
• Mol File: 61469-71-4.mol

Chemical Properties

• Boiling Point: 410.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-(2-cyano-phenylethenyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-cyano-phenylethenyl)benzonitrile(61469-71-4)
• EPA Substance Registry System: 4-(2-cyano-phenylethenyl)benzonitrile(61469-71-4)

Safety Data

• Hazardous Substances Data: 61469-71-4(Hazardous Substances Data)

Usage

Chemical Class

Benzene nitrile

Molecular Weight

261.3 g/mol

Physical State

Yellow solid

Room Temperature State

Solid

Functional Groups

Aromatic ring, Cyano (-CN) group

Reactivity

Versatile

Usage

Building block in organic synthesis
Production of dyes
Production of pharmaceuticals
Production of other organic compounds

Characteristics

Aromaticity
Presence of cyano functional groups

Properties

Color: Yellow
State: Solid at room temperature

Applications

Organic synthesis
Dye production
Pharmaceutical manufacturing

Chemical Reactivity

Ability to undergo various chemical reactions due to its functional groups

Importance

Valued for its versatile reactivity
Serves as a key intermediate in the synthesis of various compounds

Industrial Use

Widely employed in chemical industries for its role as a building block

Common Reactions

Addition reactions
Substitution reactions
Polymerization reactions

Advantages

Enhances the diversity of chemical products
Facilitates the synthesis of complex molecules

Safety Precautions

Handle with care due to potential hazards associated with chemical reactions involving cyano groups.

Upstream product

• 140-29-4 phenylacetonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 6114-57-4 (Z)-2,3-diphenylacrylonitrile 
• 130728-46-0 3c-(4-cyano-phenyl)-2-(4-methoxy-phenyl)-acrylonitrile 

Downstream Products

• 50415-75-3 3-(4-carboxy-phenyl)-2-phenyl-acrylic acid 
• 7473-70-3 phenanthrene-3,9-dicarbonitrile 
• 140-29-4 phenylacetonitrile 

Relevant articles and documents

Accelerated Discovery of α-Cyanodiarylethene Photoswitches

Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.

Antiproliferative activity and mode of action analysis of novel amino and amido substituted phenantrene and naphtho[2,1-b]thiophene derivatives

Herein we present and describe the design and synthesis of novel phenantrene derivatives substituted with either amino or amido side chains and their biological activity. Antiproliferative activities were assessed in vitro on a panel of human cancer cell lines. Tested compounds showed moderate activity against cancer cells in comparison with 5-fluorouracile. Among all tested compounds, some compounds substituted with cyano groups showed a pronounced and selective activity in the nanomolar range of inhibitory concentrations against HeLa and HepG2. The strongest selective activity against HeLa cells was observed for acrylonitriles 8 and 11 and their cyclic analogues 15 and 17 substituted with two cyano groups with a corresponding IC50 = 0.33, 0.21, 0.65 and 0.45 μM, respectively. Compounds 11 showed the most pronounced selectivity being almost non cytotoxic to normal fibroblasts. Additionally, mode of biological action analysis was performed in silico and in vitro by Western blot analysis of HIF-1-α relative expression for compounds 8 and 11.

Synthesis and characterization of phenanthrene derivatives for optoelectronic applications

New phenanthrene derivatives, bearing cyano group at selected positions, have been prepared in good yields through Knoevenagel condensation and classical oxidative photocyclization. The optical properties of the cyanophenanthrenes have been investigated b