75898-34-9

Basic information

• Product Name: 4-CYANO-2'-NITRODIPHENYL
• Synonyms: 4-CYANO-2'-NITROBIPHENYL;4-CYANO-2'-NITRODIPHENYL;2'-NITROBIPHENYL-4-CARBONITRILE;Cyanonitrodiphenyl;4-CYANO-2''-NITRODIPHENYL 98+%;2'-Nitro[1,1'-biphenyl]-4-carbonitrile;2-Nitro-4'-cyanobiphenyl;4-Cyano-2'-nitrobiphenyl 2'-Nitrobiphenyl-4-carbonitrile
• CAS NO: 75898-34-9
• Molecular Formula: C13H8N2O2
• Molecular Weight: 224.21
• Mol File: 75898-34-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 148 °C
• Boiling Point: 395.361 °C at 760 mmHg
• Flash Point: 192.908 °C
• Appearance: /
• Density: 1.304 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.641
• Solubility: slightly sol. in Tetrahydrofuran
• CAS DataBase Reference: 4-CYANO-2'-NITRODIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANO-2'-NITRODIPHENYL(75898-34-9)
• EPA Substance Registry System: 4-CYANO-2'-NITRODIPHENYL(75898-34-9)

Safety Data

• Hazardous Substances Data: 75898-34-9(Hazardous Substances Data)

Usage

General Description

4-Cyano-2'-nitrodiphenyl, also known as CNND, is a chemical compound that consists of a nitro group, a cyano group, and a diphenyl ring structure. It is primarily used as a chemical intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. CNND is known for its versatile reactivity and has been used in the production of diverse products such as insecticides, herbicides, and other specialty chemicals. Its strong electron-withdrawing groups make it useful for facilitating various organic reactions, making it a valuable component in the field of organic chemistry. Additionally, CNND has shown potential as a building block for the development of new materials and functional molecules.

InChI:InChI=1/C13H8N2O2/c14-9-10-5-7-11(8-6-10)12-3-1-2-4-13(12)15(16)17/h1-8H

Upstream product

• 2920-38-9 4-cyano-1,1'-biphenyl 
• 623-00-7 4-bromobenzenecarbonitrile 
• 5570-19-4 2-nitrophenylboronic acid 
• 88-73-3 2-Chloronitrobenzene 
• 126747-14-6 4-cyanophenylboronic acid 
• 190788-59-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 365-33-3 2-nitrobenzenediazonium tetrafluoroborate 
• 98-95-3 nitrobenzene 
• 623-03-0 4-Cyanochlorobenzene 
• 15163-59-4 potassium o-nitrobenzoate 
• 552-16-9 ortho-nitrobenzoic acid 
• 98-80-6 phenylboronic acid 

Downstream Products

• 75898-35-0 2'-amino-[1,1'-biphenyl]-4-carbonitrile 
• 57955-18-7 9H-carbazole-2-carbonitrile 

Relevant articles and documents

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling

A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).