16227-12-6

Basic information

• Product Name: 4-Phenyl-4H-1,2,4-triazole
• Synonyms: 4-Phenyl-4H-1,2,4-triazole;1H-1,2,4-Triazole, 4-phenyl-;4-Phenyl-1H-1,2,4-triazole;Brn 0115833;4H-1,2,4-Triazole, 4-phenyl-;1-Phenyl-1,3,4-triazole;4-Phenyl-1,2,4-triazole;4-phenyl-1,2,4-triazol-4-yl)phenol
• CAS NO: 16227-12-6
• Molecular Formula: C₈H₇N₃
• Molecular Weight: 145.1613
• Mol File: 16227-12-6.mol

Chemical Properties

• Boiling Point: 292℃
• Flash Point: 131℃
• Appearance: /
• Density: 1.16
• Vapor Pressure: 0.00184mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Phenyl-4H-1,2,4-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenyl-4H-1,2,4-triazole(16227-12-6)
• EPA Substance Registry System: 4-Phenyl-4H-1,2,4-triazole(16227-12-6)

Safety Data

• Hazardous Substances Data: 16227-12-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Phenyl-4H-1,2,4-triazole is used as a building block in organic synthesis for its ability to form a variety of complex organic molecules, facilitating the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Coordination Chemistry:
In coordination chemistry, 4-Phenyl-4H-1,2,4-triazole is utilized as a ligand to form stable complexes with metal ions, which are essential in catalysis, materials science, and the development of new functional materials.
Used in Plastics and Rubber Industry:
4-Phenyl-4H-1,2,4-triazole is used as a stabilizer in the production of plastics and rubber to enhance their resistance to degradation, thereby improving their durability and performance in various applications.
Used in Pharmaceutical Research:
4-Phenyl-4H-1,2,4-triazole is employed in pharmaceutical research for its potential anti-fungal, anti-tumor, and anti-inflammatory properties, making it a promising candidate for the development of new therapeutic agents.
Used in Biochemistry:
In the field of biochemistry, 4-Phenyl-4H-1,2,4-triazole is studied for its interactions with biological systems, offering insights into its potential applications in diagnostics, therapeutics, and the understanding of biological processes.

InChI:InChI=1/C8H7N3/c1-2-4-8(5-3-1)11-6-9-10-7-11/h1-7H

Upstream product

• 5373-72-8 4-phenyl-Δ²-1,2,4-triazoline-5-thione 
• 1068-57-1 acetic acid hydrazide 
• 103-70-8 Formanilid 
• 624-84-0 formic acid hydrazide 
• 628-36-4 diformylhydrazine 
• 177028-52-3 3-Diethoxymethyl-4-phenyl-4H-[1,2,4]triazole 
• 103-72-0 phenyl isothiocyanate 
• 16227-06-8 N,N-dimethylformamide azine dihydrochloride 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 288-88-0 1,2,4-Triazole 
• 16227-06-8 {N'-[(dimethylamino)methylene]-N,N-dimethylhydrazonoformamide dihydrochloride} 
• 177028-40-9 5-Diethoxymethyl-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 

Downstream Products

• 114505-98-5 anhydro-2,7-diphenyl-1-hydroxy-3-oxopyrrolo<1,2-b>-1,2,4-triazolium hydroxide 
• 120337-45-3 1-benzyl-4-phenyl-1,2,4-triazolium chloride 
• 120317-71-7 C₉H₁₀N₃⁽¹⁺⁾*CH₃O₄S^(1-) 
• 83096-19-9 4-phenyl-1,2,4-triazolium-1-dicyanomethylide 
• 73045-93-9 1-(4'-bromophenacyl)-4-phenyl-1,2,4-triazol-1-ium bromide 
• 288-88-0 1,2,4-Triazole 
• 249646-17-1 4-chlorobenzoyl 4-phenyl-1,2,4-triazol-1-ium 2,4,6-trinitrophenylmethylide 
• 249646-16-0 4-methoxybenzoyl 4-phenyl-1,2,4-triazol-1-ium 2,4,6-trinitrophenylmethylide 
• 249646-15-9 4-bromobenzoyl 4-phenyl-1,2,4-triazol-1-ium 2,4,6-trinitrophenylmethylide 
• 73620-01-6 C₁₆H₁₂N₄O₃ 
• 1416802-45-3 4-phenyl-3,5-bis((3,4,5-tris(dodecyloxy)phenyl)ethynyl)-4H-1,2,4-triazole 

Relevant articles and documents

BENZOXAZOLE DERIVATIVES AND FLUORESCENT MATERIAL COMPRISING THE SAME

A benzoxazole derivative represented by Structural Formula 1 is provided. Thus, the present invention is not limited thereto. A fluorescent material is provided to remarkably improve fluorescence yield, to have excellent dyeing property and dispersibility, to minimize environmental pollution and to improve economic feasibility. Structural 1.

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme-ligand interactions. Here, we present experimental data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, molecular dynamics simulations, and density functional theory calculations. Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two additional scaffolds but also provide a model to predict the activities of novel scaffolds.

Spin Crossover in Dinuclear N4S2 Iron(II) Thioether-Triazole Complexes: Access to [HS-HS], [HS-LS], and [LS-LS] States

Access to a new family of thioether-linked PSRT ligands, 4-substituted-3,5-bis{[(2-pyridylmethyl)sulfanyl]methyl}-4H-1,2,4-triazoles (analogues of the previously studied amino-linked PMRT ligands), has been established. Four such ligands have been prepared, PSPhT, PSiBuT, PSt-BuPhT, and PSMePhT, with R = Ph, iBu, t-BuPh, and MePh, respectively. Three dinuclear colorless to pale green iron(II) complexes, [FeII2(PSRT)2](BF4)4·solvent, featuring N4S2 donor sets, were prepared. Single-crystal structure determinations on [FeII2(PSPhT)2](BF4)4·2MeCN·H2O, [FeII2(PSPhT)2](BF4)4·21/2MeCN·1/2H2O·THF, [FeII2(PSMePhT)2](BF4)4·2MeCN, and [FeII2(PSiBuT)2](BF4)4·4MeCN reveal that all four are stabilized in the [HS-HS] state to 100 K and that both possible binding modes of the bis-terdentate ligands, cis- and trans-axial, are observed. Variable-temperature magnetic susceptibility studies of air-dried crystals (solvatomorphs of the single crystal samples) reveal the first examples of spin crossover (SCO) for a dinuclear iron(II) complex with N4S2 coordination. Specifically, [FeII2(PSPhT)2](BF4)4·21/2H2O undergoes a multistep but complete SCO from [HS-HS] to [LS-LS], whereas [FeII2(PSMePhT)2](BF4)4·11/2MeCN·2H2O exhibits a half-SCO from [HS-HS] to [HS-LS]. In contrast, [FeII2(PSiBuT)2](BF4)4·MeCN·H2O remains [HS-HS] down to 50 K. The reflectance spectrum of pale green [FeII2(PSPhT)2](BF4)4·1/2CHCl3·21/2H2O (solvatomorph A) reveals a trace of LS character (572 nm band 1A1g → 1T1g). Evans' 1H NMR method and UV-vis spectroscopy studies revealed that on cooling dark green acetonitrile solutions of these complexes from 313 to 233 K, all three undergo SCO centered at or near room temperature. The tendency of the complexes to go LS in solution reflects the electronic impact of R on the σ-donor strength of the PSRT ligand, whereas the opposite trend in stabilization of the LS state is seen in the solid state, where crystal packing effects, of the R group and solvent content, dominate the SCO behavior.

Synthesis of xylylene-bridged dipalladium complexes with imidazole and triazole-based di-N-heterocyclic carbene (NHC) ligands

The di-N-heterocyclic carbene (NHC) dipalladium complexes, [(PdPyBr2)2(di-NHCimi)] and [(PdPyBr2)2(di-NHCtri)], di-NHCimi and di-NHCtri represent an imidazolylidene and a triazolylidene, respectively, featuring a 1,4-xylylene spacer between the carbene units, have been prepared. The influences of the imidazolylidene and triazolidene backbone and different substituents on the catalytic activity have been investigated in the Mizoroki-Heck reaction of styrene with bromobenzene.

Syntheses, structural variation, and characterization of a series of crystalline coordination compounds with 4-benzene-1,2,4-triazole: Polymorph, incomplete spin transition, and single crystal-to-single crystal transformation

Based on the 4-substituted 1,2,4-triazole derivate ligand 4-benzene-1,2,4-triazole (L), a series of crystalline coordination complexes varying from mononuclear to trinuclear species, namely, [Zn(L) 2Br2] (1), [Zn(L)2Br2] (2), [Fe(L)4(NCS)2]2 (3), [Fe2(μ 2-L)3(L)2(NCS)4]·CH 3OH·CH3CH2OH (4), [Fe 2(μ2-L)3(L)2(NCS) 4]·2CH3CH2OH (5), [Fe 2(μ2-L)3(L)2(NCS) 4]·2CH3CH2OH·1.5H2O (6), and [Ni3(μ2-L)6(L)4(H 2O)2](NO3)6·15.5H 2O (7), have been isolated. 1 and 2 present a temperature-induced polymorphic phenomenon of two zinc(II) coordination complexes with L. The solvent effect plays the key role for the self-assembly of these Fe(II) complexes 3-6: 3 contains mononuclear Fe(L)4(NCS)2 units without spin-transition behavior, whereas both 4 and 5 present binuclear Fe(II) complexes with three N1,N2-1,2,4-triazole bridges exhibiting incomplete spin-transition behavior. The low-temperature X-ray structural analysis (100 K) of 4 also confirms that one of the Fe(II) centers is located at the low-spin (LS) state and the other Fe(II) center is located at the high-spin (HS) state. Interestingly, when the binuclear Fe(II) complex 5 was exposed in the water atmosphere, solvent-induced single crystal-to-single crystal transformation can be observed, and the binuclear Fe(II) complex 6 exhibiting antiferromagnetic interactions can be isolated. Further, a trinuclear crystalline compound is isolated when Ni(II) salts were used to react with L. Variable-temperature magnetic susceptibility measurement (2-300 K) reveals antiferromagnetic interactions in 7. The polymorphic phenomenon (1 and 2), incomplete spin-transition phenomenon (4 and 5), and single crystal-to-single crystal transformation (from 5 to 6) also reveal great potential in the construction of these novel functional materials with L.

Effect of N 4-substituent choice on spin crossover in dinuclear iron(II) complexes of bis-terdentate 1,2,4-triazole-based ligands

Seven new dinuclear iron(II) complexes of the general formula [Fe II2(PMRT)2](BF4)4· solvent, where PMRT is a 4-substituted-3,5-bis{[(2-pyridylmethyl)-amino]methyl}- 4H-1,2,4-triazole, have been prepared in order to investigate the substituent effect on the spin crossover event. Variable temperature magnetic susceptibility and 57Fe Moessbauer spectroscopy studies show that two of the complexes, [FeII2(PMPT)2](BF4) 4·H2O (N4 substituent is pyrrolyl) and [FeII2(PMPhAT)2](BF 4)4 (N4 is N,N-diphenylamine), are stabilized in the [HS-HS] state between 300 and 2 K with weak antiferromagnetic interactions between the iron(II) centers. Five of the complexes showed gradual half spin crossover, from [HS-HS] to [HS-LS], with the following T1/2 (K) values: 234 for [FeII2(PMibT)2](BF 4)4·3H2O (N4 is isobutyl), 147 for [FeII2(PMBzT)2](BF4) 4 (N4 is benzyl), 133 for [FeII 2(PMCF3PhT)2](BF4) 4·DMF·H2O (N4 is 3,5-bis(trifluoromethyl)phenyl), 187 for [FeII2(PMPhT) 2](BF4)4 (N4 is phenyl), and 224 for [FeII2(PMC16T)2](BF 4)4 (N4 is hexadecyl). Structure determinations carried out for three complexes, [FeII2(PMPT) 2](BF4)4·4DMF, [FeII 2(PMBzT)2](BF4)4·CH 3CN, and [FeII2(PMPhAT) 2](BF4)4·solvent, revealed that in all three complexes both iron(II) centers are stabilized in the high spin state at 90 K. A general and reliable 4-step route to PMRT ligands is also detailed.

Tris(carbene)borate ligands featuring imidazole-2-ylidene, benzimidazol-2-ylidene, and 1,3,4-triazol-2-ylidene donors. Evaluation of donor properties in four-coordinate {NiNO}10 complexes

The synthesis and characterization of new tris(carbene)borate ligand precursors containing substituted benzimidazol-2-ylidene and 1,3,4-triazol-2-ylidene donor groups, as well as a new tris(imidazol-2-ylidene) borate ligand precursor are reported. The relative donor strengths of the tris(carbene)borate ligands have been evaluated by the position of νNO) in four-coordinate {NiNO}10 complexes, and follow the order: imidazol-2-ylidene > benzimidazol-2-ylidene > 1,3,4-triazol-2-ylidene. There is a large variation in νNO), suggesting these ligands to have a wide range of donor strengths while maintaining a consistent ligand topology. All ligands are stronger donors than Tp* and Cp*.

1,2,4-triazole-based tunable aryl/alkyl ionic liquids

Ionic liquids based on aryl-/alkyl-substituted imidazolium salts constitute a new generation of ionic liquids with a high degree of flexibility. The new concept could now also be extended to aryl-/alkyl-substituted 1,2,4-triazolium salts. The two differen

Salts Comprising Aryl-Alkyl-Substituted Imidazolium and Triazolium Cations and the Use Thereof

The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts

Cu(OAc)2·H2O-catalyzed N-arylation of nitrogen-containing heterocycles

In the absence of any additional ligands, the efficient N-arylation of nitrogen-containing heterocycles with aryl iodides catalyzed by relative low catalyst amount of Cu(OAc)2·H2O was developed. This simple catalytic system is involved in the C-N cross-coupling reaction and works for a variety of pyrazole, pyrrole, imidazole, triazole, indole, benzoimidazole, benzotriazole, carbazole, and anilines as well as aryl iodides with different electronic properties. Highly efficient copper(II)-catalyzed N-arylation protocol was established.