1453-81-2

Basic information

• Product Name: 1-Phenyl-1H-1,2,3-triazole
• Synonyms: 1-Phenyl-1H-1,2,3-triazole
• CAS NO: 1453-81-2
• Molecular Formula: C₈H₇N₃
• Molecular Weight: 145.1613
• Mol File: 1453-81-2.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 280.2°Cat760mmHg
• Flash Point: 123.2°C
• Appearance: /
• Density: 1.16g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1-Phenyl-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-1H-1,2,3-triazole(1453-81-2)
• EPA Substance Registry System: 1-Phenyl-1H-1,2,3-triazole(1453-81-2)

Safety Data

• Hazardous Substances Data: 1453-81-2(Hazardous Substances Data)

Usage

General Description

1-Phenyl-1H-1,2,3-triazole is an organic compound with the molecular formula C9H7N3. It is an aromatic azole compound that contains a 1,2,3-triazole ring and a phenyl group. This chemical is commonly used in the synthesis of pharmaceuticals, agrochemicals, and materials science. It has a variety of applications in organic synthesis, such as in the formation of triazolyl-containing compounds and as a ligand in metal-catalyzed reactions. Additionally, 1-Phenyl-1H-1,2,3-triazole has been studied for its potential biological activities and has shown promise as a potential anticancer agent. Overall, this compound has versatile chemical properties that make it useful in a range of applications in the field of chemistry and biochemistry.

Upstream product

• 622-37-7 Phenyl azide 
• 74-86-2 acetylene 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 108429-48-7 1-phenyl-4,5-dihydro-5-hydroxy-1H-1,2,3-triazole 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 
• 19019-88-6 7-isopropylidene-2,3-dicarbomethoxynorbornadiene 
• 1112-00-1 trimethylstannylacetylene 
• 109853-57-8 4-tert-butyl-3,3-dimethyl-5-methylene-Δ¹-1,2,4-triazoline 
• 2117-50-2 bis(trimethyltin)acetylene 
• 56020-01-0 N′-(2,2-dichloroethylidene)-4-methylbenzenesulfonohydrazide 
• 62-53-3 aniline 
• 208645-11-8 N-methanesulfonic 2,2-dichloroethylidene Hydrazide 
• 288-36-8 1,2,3-triazole 

Downstream Products

• 3198-98-9 dimethyl 1-phenyl-1H-pyrazole-3,4-dicarboxylate 
• 173654-00-7 5-[(1R,2S)-2-(3,4-dichlorophenyl)-1-hydroxy-4-pentenyl]-1-phenyl-1,2,3-(1H)-triazole 
• 1072456-82-6 2,6-bis(3-phenyl-1H-1,2,3-triazol-5-yl)pyridine 
• 869336-36-7 5-(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole 
• 4874-85-5 1,5-diphenyl-1H-1,2,3-triazole 
• 68809-45-0 5-(4-methylphenyl)-1-phenyl-1H-1,2,3-triazole 

Relevant articles and documents

Phosphorescent cationic iridium(III) complexes with cyclometalating 1H-indazole and 2H-[1,2,3]-triazole ligands

Two new cationic iridium(III) complexes with cyclometalating 1-phenylindazole or 2-phenyl-1,2,3-triazole ligands, [(C^N)2Ir(4, 4′-di-tert-butyl-2,2′-dipyridyl)](PF6), exhibit yellow or green phosphorescence with quantum yields and ex

[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles

1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.

Using Small Molecules to Enhance P450 OleT Enzyme Activity in Situ

Cytochrome P450 OleT is a fatty acid decarboxylase that catalyzes the production of olefins with biofuel and synthetic applications. However, the relatively sluggish catalytic efficiency of the enzyme limits its applications. Here, we report the application of a novel class of benzene containing small molecules to improve the OleT activity. The UV-Vis spectroscopy study and molecular docking results confirmed the high proximity of the small molecules to the heme group of OleT. Up to 6-fold increase of product yield has been achieved in the small molecule-modulated enzymatic reactions. Our work thus sheds the light to the application of small molecules to increase the OleT catalytic efficiency, which could be potentially used for future olefin productions.

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.