6085-94-5

Basic information

• Product Name: 1-BENZYL-1,2,4-TRIAZOLE
• Synonyms: 1-BENZYL-1,2,4-TRIAZOLE;1-benzyl-1h-1,2,4-triazole;4-triazole,1-(phenylmethyl)-1h-2;4-triazole,1-benzyl-1h-2;1-Phenylmethyl-1H-1,2,4-triazole;L-22080
• CAS NO: 6085-94-5
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.19
• Mol File: 6085-94-5.mol

Chemical Properties

• Boiling Point: 321.6 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: /
• Density: 1.13 g/cm³
• Vapor Pressure: 0.000294mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 1-BENZYL-1,2,4-TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-1,2,4-TRIAZOLE(6085-94-5)
• EPA Substance Registry System: 1-BENZYL-1,2,4-TRIAZOLE(6085-94-5)

Safety Data

• Hazardous Substances Data: 6085-94-5(Hazardous Substances Data)

Usage

Uses

Used in Organometallic Chemistry:
1-Benzyl-1,2,4-triazole serves as a valuable ligand in organometallic chemistry, contributing to the development of novel metal complexes with potential applications in catalysis and other areas.
Used in Pharmaceutical Industry:
Leveraging its antifungal and antimicrobial properties, 1-benzyl-1,2,4-triazole is utilized in the development of new pharmaceuticals targeting a variety of infections and diseases.
Used in Agrochemicals:
1-BENZYL-1,2,4-TRIAZOLE's antifungal and antimicrobial characteristics also make it suitable for use in agrochemicals, where it can help protect crops from various pathogens and pests.
Used in Material Science:
1-Benzyl-1,2,4-triazole has been studied for its potential use as a corrosion inhibitor, which can be beneficial in extending the lifespan of materials used in various industries.
Used in Polymer Stabilization:
As a stabilizer in polymer materials, 1-benzyl-1,2,4-triazole can enhance the durability and performance of polymers, making them more resistant to degradation and other environmental factors.

InChI:InChI=1/C9H9N3/c1-2-4-9(5-3-1)6-12-8-10-7-11-12/h1-5,7-8H,6H2

Upstream product

• 288-88-0 1,2,4-Triazole 
• 100-44-7 benzyl chloride 
• 108223-02-5 1-Methyl-5-(1,2,4-triazolyl)phosphonic acid diethyl ester 
• 16227-13-7 4-benzyl-4H-1,2,4-triazole 
• 100-51-6 benzyl alcohol 
• 41253-21-8 sodium triazole 
• 584-13-4 4-amino-1,2,4-triazole 
• 25857-87-8 1-benzyl-1,2,4-triazolio-4-benzoylamidat 
• 6085-98-9 4-amino-1-benzyl-1,2,4-triazolium chloride 
• 100-39-0 benzyl bromide 
• 18293-54-4 1-trimethylsilyl-1,2,4-triazole 

Downstream Products

• 66519-70-8 2-benzyl-2H-benzo[d][1,2,3]triazole 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 535961-27-4 1-benzyl-5-phenylthio-1H-1,2,4-triazole 
• 349102-47-2 (1-benzyl-1H-[1,2,4]triazol-4-io)(4-methoxybenzoyl)(2,4,6-trinitrophenyl)methanide 
• 349102-50-7 {4-[2-(4-methoxyphenyl)-2-oxoethyl]-4H-[1,2,4]triazol-1-io}(phenyl)(2,4,6-trinitrophenyl)methanide 
• 349102-46-1 (1-benzyl-1H-[1,2,4]triazol-4-io)(4-bromobenzoyl)(2,4,6-trinitrophenyl)methanide 
• 349102-49-4 {4-[2-(4-bromophenyl)-2-oxoethyl]-4H-[1,2,4]triazol-1-io}(phenyl)(2,4,6-trinitrophenyl)methanide 
• 349102-48-3 (1-benzyl-1H-[1,2,4]triazol-4-io)(4-nitrobenzoyl)(2,4,6-trinitrophenyl)methanide 
• 349102-51-8 {4-[2-(4-nitrophenyl)-2-oxoethyl]-4H-[1,2,4]triazol-1-io}(phenyl)(2,4,6-trinitrophenyl)methanide 
• 263152-04-1 1-benzyl-1H-[1,2,4]triazol-4-iumbenzoyl-2,4,6-trinitrophenylmethylide 
• 263152-05-2 1-benzyl-1H-[1,2,4]triazol-4-ium-4-methylbenzoyl-2,4,6-trinitrophenylmethylide 
• 861162-30-3 1-(1-benzyl-1H-1,2,4-triazol-5-yl)-2-ethylbutan-1-ol 
• 1435949-32-8 [(1-benzyl-5-(diphenylphosphino)-1H-1,2,4-triazole)(triphenylphosphine)2Cu₂I₂] 

Relevant articles and documents

Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases

We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl, TMPMgCl

N-difluoromethylazole sulfur (selenium) urea derivative and preparation method thereof

The invention discloses an N-difluoromethylazole sulfur (selenium) urea derivative and a preparation method thereof. The N-difluoromethylazole sulfur (selenium) urea derivative comprises N-difluoromethyl benzimidazole sulfourea, N-difluoromethyl imidazole sulfourea, N-difluoromethyl triazole sulfourea and an relevant N-difluoromethyl selenourea derivative; and a benzimidazole derivative, an imidazole derivative or a triazole derivative, elemental sulfur powder or selenium powder, and a catalyst are added into a reaction tube, an organic solvent is added into the reaction tube, halohydrocarbonis injected into the reaction tube, and reacting is carried out under a heating condition to obtain the N-difluoromethylazole sulfur (selenium) urea derivative. The preparation method is simple and easy to operate, the condition is mild, the cheap and economical effects are achieved, and the provided compounds have important potential application value in pesticides, medicines and organic functional materials.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

N-Alkylation of amines with alcohols over nanosized zeolite beta

Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

Heteroleptic, dinuclear copper(i) complexes for application in organic light-emitting diodes

A series of highly luminescent, heteroleptic copper(I) complexes has been synthesized using a modular approach based on easily accessible P^N ligands, triphenylphosphine, and copper(I) halides, allowing for an independent tuning of the emission wavelength

Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors

A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole 1. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 μM), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen.

Solvent-free synthesis of some triazole-based bis(N-heterocyclic carbene) ligands

Two series of bistriazolium dibromides with different alkyl bridged length (n = 2-4) were synthesised through a simple solvent-free method. Six of these compounds were prepared from the reaction of 1-R-1H-1,2,4-triazole with dibromoalkane in moderate to excellent yield (45-98%). However, the other six compounds were prepared from the reaction of alkyl bridged bistriazole with bromoalkane in 55-99% yield. All compounds are new and were fully characterised by IR, NMR and elemental analyses.

Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions

The rate constants for the reactions of a variety of nucleophiles reacting with substituted benzyl chlorides in liquid ammonia (LNH3) have been determined. To fully interpret the associated linear free-energy relationships, the ionization constants of phenols ions in liquid ammonia were obtained using UV spectra. These equilibrium constants are the product of those for ion-pair formation and dissociation to the free ions, which can be separated by evaluating the effect of added ammonium ions. There is a linear relationship between the pKa of phenols in liquid ammonia and those in water of slope 1.68. Aminium ions exist in their unprotonated free base form in liquid ammonia and their ionization constants could not be determined by NMR. The rates of solvolysis of substituted benzyl chlorides in liquid ammonia at 25 °C show a Hammett ρ of zero, having little or no dependence upon ring substituents, which is in stark contrast with the hydrolysis rates of substituted benzyl halides in water, which vary 107 fold. The rate of substitution of benzyl chloride by substituted phenoxide ions is first order in the concentration of the nucleophile indicative of a SN2 process, and the dependence of the rate constants on the pKa of the phenol in liquid ammonia generates a Bronsted βnuc = 0.40. Contrary to the solvolysis reaction, the reaction of phenoxide ion with 4-substituted benzyl chlorides gives a Hammett ρ = 1.1, excluding the 4-methoxy derivative, which shows the normal positive deviation. The second order rate constants for the substitution of benzyl chlorides by neutral and anionic amines show a single Bronsted βnuc = 0.21 (based on the aqueous pKa of amine), but their dependence on the substituent in substituted benzyl chlorides varies with a Hammett ρ of 0 for neutral amines, similar to that seen for solvolysis, whereas that for amine anions is 0.93, similar to that seen for phenoxide ion.(Figure Presented)

Synthesis and structure-activity relationship of a novel series of heterocyclic sulfonamide γ-secretase inhibitors

γ-Secretase inhibitors have been shown to reduce the production of β-amyloid, a component of the plaques that are found in brains of patients with Alzheimer's disease. A novel series of heterocyclic sulfonamide γ-secretase inhibitors that reduce β-amyloid levels in cells is reported. Several examples of compounds within this series demonstrate a higher propensity to inhibit the processing of amyloid precursor protein compared to Notch, an alternative γ-secretase substrate.

Synthesis of chiral primary amines: diastereoselective alkylation of N-[(1E)-alkylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amin es and N4-Nexocyclic bond cleavage in the resulting 1,2,4-triazol-4-alkylamines

Enantiomerically pure 3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine 14a and 3,5-bis[(1S)-1-ethoxyethyl]-4H-1,2,4-triazol-4-amine 14b were used as chiral auxiliaries to obtain enantiomerically enriched α-aminoacetals, primary alkyl and arylalkyl amines (ee ranging from 40% to 90%). The different stages of the process were imine formation from the corresponding aldehydes, diastereoselective addition of a Grignard reagent, quaternization of the triazole auxiliary and cleavage of the N4-Nexocyclic bond by LiBH4. The mechanism of the cleavage of the N4-Nexocyclic bond is supported by the use of deuterated metal hydride. The absolute configurations of the new stereogenic centres were established by X-ray analyses of the enantiomerically pure stereomers isolated by semi-preparative liquid chromatography on a chiral support.