21874-06-6

Basic information

• Product Name: 4-Phenylcinnoline
• Synonyms: 4-Phenylcinnoline;Cinnoline, 4-phenyl-
• CAS NO: 21874-06-6
• Molecular Formula: C₁₄H₁₀N₂
• Molecular Weight: 206.25
• Mol File: 21874-06-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Phenylcinnoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylcinnoline(21874-06-6)
• EPA Substance Registry System: 4-Phenylcinnoline(21874-06-6)

Safety Data

• Hazardous Substances Data: 21874-06-6(Hazardous Substances Data)

Usage

General Description

4-Phenylcinnoline is a chemical compound with the formula C17H13N. It is a polycyclic aromatic hydrocarbon that consists of a cinnoline ring system fused to a phenyl ring, and it is commonly used as a building block in the synthesis of various pharmaceuticals and organic compounds. 4-Phenylcinnoline is a yellow crystalline solid with a molecular weight of 235.29 g/mol and a melting point of 222-224°C. It is known to possess anti-inflammatory, anti-cancer, and anti-bacterial properties, and its unique structure makes it a valuable tool for drug discovery and medicinal chemistry research. Additionally, 4-Phenylcinnoline is also used as a fluorescent probe in biological imaging and studies.

Upstream product

• 7647-01-0 hydrogenchloride 
• 412305-23-8 4-phenyl-1,2-dihydro-cinnoline 
• 64-17-5 ethanol 
• 64097-92-3 2-(1-phenylvinyl)aniline 
• 2364-50-3 isovaleranilide 
• 62-53-3 aniline 
• 536-74-3 phenylacetylene 
• 5152-84-1 4-chlorocinnoline 
• 98-80-6 phenylboronic acid 
• 187463-09-8 (Z)-1-(2-bromovinyl)-2-chlorobenzene 
• 24009-93-6 diethyl dihydrocinnoline-1,2-dicarboxylate 
• 1393462-68-4 C₁₄H₁₅ClN₂O₄ 
• 1393462-69-5 diethyl 4-phenyldihydrocinnoline-1,2-dicarboxylate 
• 108-24-7 acetic anhydride 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 
• 412305-23-8 4-phenyl-1,2-dihydro-cinnoline 
• 91330-47-1 5-phenyl-pyridazine-3,4-dicarboxylic acid 
• 26631-10-7 4-isopropylidene-1,1-dimethyl-7-phenyl-[1,3,4]oxadiazino[4,3-a]cinnolin-2-one 

Relevant articles and documents

Iridium-Catalyzed α-Selective Arylation of Styrenes by Dual C?H Functionalization

An IrI-system modified with a ferrocene derived bisphosphine ligand promotes α-selective arylation of styrenes by dual C?H functionalization. These studies offer a regioisomeric alternative to the Pd-catalyzed Fujiwara–Moritani reaction.

Pd-assisted cross-coupling reactions with 4-chlorocinnoline

A series of 4-ethynylcinnolines 3a-e was prepared by Sonogashira reaction of 4-chlorocinnoline (1) with appropriate alkynes. Moreover, Suzuki coupling of with boronic esters gave the corresponding 4-arylcinnolines 5a-c. Detailed NMR spectroscopic data including unambiguous chemical shift assignments of all 1H, 13C, and 15N resonances of the obtained cinnoline derivatives are reported.

Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides

(Chemical Equation Presented) Azides to indoles: Dirhodium(II)-catalyzed decomposition of aryl azides was developed as a mild, functional group tolerant method for the synthesis of indoles (see scheme).