185316-58-9

Basic information

• Product Name: 5-PHENYL-1H-INDAZOLE
• Synonyms: 5-PHENYL-1H-INDAZOLE;1H-Indazole, 5-phenyl-
• CAS NO: 185316-58-9
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.23
• EINECS: 604-604-1
• Mol File: 185316-58-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 405.131 °C at 760 mmHg
• Flash Point: 192.137 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: 2-8°C
• PKA: 13.81±0.40(Predicted)
• CAS DataBase Reference: 5-PHENYL-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-1H-INDAZOLE(185316-58-9)
• EPA Substance Registry System: 5-PHENYL-1H-INDAZOLE(185316-58-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 185316-58-9(Hazardous Substances Data)

Usage

General Description

5-Phenyl-1H-indazole is a chemical compound with the molecular formula C14H11N. It is a heterocyclic aromatic compound that consists of a benzene ring fused to an indazole ring. 5-PHENYL-1H-INDAZOLE has a variety of industrial and pharmacological applications, including use as a building block in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential therapeutic effects, particularly as a potential treatment for neurological and psychiatric disorders. Additionally, 5-Phenyl-1H-indazole has been investigated for its potential as a ligand in coordination chemistry, as well as its use in electronics and material science.

InChI:InChI=1/C13H10N2/c1-2-4-10(5-3-1)11-6-7-13-12(8-11)9-14-15-13/h1-9H,(H,14,15)

Upstream product

• 108-86-1 bromobenzene 
• 864771-44-8 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate 
• 210556-89-1 2-formyl-4-phenyl-cyclohexanone 

Downstream Products

• 1338792-00-9 3-(5-phenyl-1H-indazol-3-yl)benzenesulfonamide 
• 1338795-62-2 3-iodo-5-phenyl-1H-indazole 

Relevant articles and documents

5-phenylindazole

The title compound, C13H10N2, packs in chains along the a axis via N - H...N hydrogen bonds that are stronger and more linear than those observed in unsubstituted indazole. These chains are linked by C - H...N and C - H...phenyl contacts along b, giving rise to a wave-like structure.

Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50 = 3.6 nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.