25699-89-2

Basic information

• Product Name: 4-(1H-1,2,4-triazol-1-yl)benzonitrile
• Synonyms: 4-(1H-1,2,4-triazol-1-yl)benzonitrile
• CAS NO: 25699-89-2
• Molecular Formula: C₉H₆N₄
• Molecular Weight: 170.17074
• Mol File: 25699-89-2.mol

Chemical Properties

• Melting Point: 167-169 °C
• Boiling Point: 376.8±44.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 1.72±0.10(Predicted)
• CAS DataBase Reference: 4-(1H-1,2,4-triazol-1-yl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1H-1,2,4-triazol-1-yl)benzonitrile(25699-89-2)
• EPA Substance Registry System: 4-(1H-1,2,4-triazol-1-yl)benzonitrile(25699-89-2)

Safety Data

• Hazardous Substances Data: 25699-89-2(Hazardous Substances Data)

Upstream product

• 288-88-0 1,2,4-Triazole 
• 623-03-0 4-Cyanochlorobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 143426-50-0 [4-(1H-1,2,4-triazol-1-yl)phenyl]methanol 
• 619-72-7 4-nitrobenzonitrile 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 17672-27-4 4-hydrazinobenzonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 77287-34-4 formamide 

Downstream Products

• 1423810-54-1 1-(1H-1,2,3,4-tetrazo-5-yl)-4-(1H-1,2,4-triazo-1-yl)benzene 

Relevant articles and documents

A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions

Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.

Preparation method of diarylamine compound

The invention relates to a preparation method of a diarylamine compound. Specifically, under the catalysis of cuprous oxide supported by chitosan, the arylation reaction used for a nitrogen-containingheterocyclic compound is achieved, and the corresponding diarylamine compound is obtained. The preparation method of the diarylamine compound has the advantages that the process conditions are simple, the yield is good, the operability is strong, and the functional group tolerance is wide.

A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles

A novel electrochemical route has been developed for the synthesis of 1,5-disubstituted and 1-aryl 1,2,4-triazoles from aryl hydrazines, paraformaldehyde, NH4OAc, and alcohols. In this multicomponent reaction system, alcohols act as solvents as well as reactants and NH4OAc is used as the nitrogen source. With the assistance of reactive iodide radical or I2 and NH3 electrogenerated in situ, this process could effectively avoid the use of strong oxidants and transition-metal catalysts and be smoothly carried out at room temperature to give a wide array of 1,2,4-triazole derivatives in good to high yields. Preliminary studies reveal that the reaction mechanism involves a radical process.

Practical CuCl/DABCO/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant

A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCl/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature. A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.

Strategically designed azolyl-carboxylate MOFs for potential humid CO2 capture

Development of solid sorbents with optimal CO2 capture characteristics is key to improving the efficiency of PSA based CO2 separation. Of the several potential sorbents, metal organic frameworks (MOFs) hold a key niche. This is owing to their modular tunable structures and manipulatable adsorption sites. Yet, developing a MOF that meets the multiple demands of a gas-separation sorbent remains a challenge. Particularly, tuning them to adsorb CO2 over the more polar water is quite difficult. The presence of highly polarizing metal centers and oxygen-rich sites in MOFs makes it difficult to retain their CO2 adsorption capacities under humid gas streams. However, tailoring the organic framework to incorporate humid CO2 capture properties should be feasible. Along these lines, here we have developed a family of iso-structural MOFs built from bi-functional ligands that carry basic azolyl and chelating carboxylate groups together. Importantly, the framework is built by employing acetate moieties as ‘modulators’; they provide a hydrophobic lining to the pore-walls. This not only enables selective adsorption of CO2, but also helps retain about 80% of the capture capacity even upon exposure to 75% RH. Along with its other advantageous features: high CO2 uptake and selectivity (3 mmol g?1 and s(CO2-N2) = ～500 for 85N2?:?15CO2@303 K); surface area: ～700 m2 g?1, working capacity: 2.6 mmol g?1; optimal HOA (22-30 kJ mol?1) and CO2 kinetics (Dc = 1.02 × 10?8 m2 s?1), these MOFs can qualify as efficient candidates for humid CO2 capture. Furthermore, we identify the most-favorable CO2 adsorption sites via simulated annealing methods, from which the presence of polarized CO2 molecules located adjacent to the π-electron rich pore walls can be seen. Importantly, these polarized molecules form T-shaped configurations among themselves via C(δ+ve)?O(δ?ve) interactions resembling those found in solid CO2, a cooperative feature that is not observed in the other CO2 molecules in the structure, which are not proximal to the polarizing walls.

Zn(II) and Cd(II) coordination networks based on N-donor ligands: Synthesis, crystal structures, and sensing of nitroaromatic explosives

Four novel coordination networks based on N-donor ligand, [Zn(L)Cl]n (1), [Cd2(L)Cl3]n (2), [Zn(L)2(H2O)2]n (3), and [Cd(L)2(H2O)2]n (4) (HL = 5-(4-(1,2,4)triazol-1-yl-phenyl-1H-tetrazole) were synthesized and structurally characterized by single crystal X-ray diffraction, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), infrared spectrophotometry (IR), and elemental analysis. The structure of 1 displays a two-dimensional (2D) structure with (6, 3) topology, which extends to a three-dimensional (3D) supramolecular network by C-H?Cl weak interactions, compound 2 can be described as a 3D 5,9-connected network based on the assembly of binuclear cadmium clusters and L ligands. Ligand in 3 and 4 is synthesized in situ, the complexes are isostructural and possess one-dimensional (1D) double chains, which further connect by O-H?N weak interactions to form 2D supramolecules. The configurations of 1-4 span from 1D, 2D to 3D network, which indicates that metal ions, counterions and weak interactions play important roles in the formation of the coordination polymers. Furthermore, all compounds exhibit high sensitivity sensing responses to nitroaromatic explosives.

A 1,10-phenanthrene rowling-N-Monoxide derivatives ligand and its application

The invention relates to a 1,10-Phenanthroline monohydrate-dual N-monoxide derivative ligand. The derivative ligand has a structural formula as follows: FORMULA, wherein R1 and R8 are selected from hydrogen, halogen, hydroxyl, C1-C7 alkoxyl, straight-chain saturated or unsaturated C1-C6 alkyl, or branched-chain saturated or unsaturated C1-C6 alkyl; R2 to R7 are selected from hydrogen, halogen, hydroxyl, C1-C8 alkoxyl, straight-chain saturated or unsaturated C1-C6 alkyl, or branched-chain saturated or unsaturated C1-C6 alkyl, C3-C7 ring hydroxyl, benzyl, aryl or 5-7 membered heterocyclic ring. Hetero atoms (such as O or N) are contained in the ligand disclosed by the invention, and a transitional six-membered ring is formed through coordination with copper ions, so that aryl iodide, aryl bromide or aryl chloride is promoted to carry out a C-N coupling reaction with aliphatic amine or secondary aliphatic cyclammonium or aliphatic acid or nitrogen-containing heterocyclic compounds at room temperature.

Heterogeneous sequential N-arylation of N-heterocycles over copper anchored mesoporous silica catalyst

N-Arylation reaction of N-heterocyclic compounds has been carried out in excellent yield using copper anchored SBA-15 catalyst. Sequential N-arylation reactions employing single catalyst under heterogeneous condition provides a straightforward access to a

Microwave-assisted catalyst-free synthesis of substituted 1,2,4-triazoles

A simple, efficient, and mild method has been developed for the synthesis of substituted 1,2,4-triazoles from hydrazines and formamide under microwave irradiation. The reaction proceeds smoothly in the absence of a catalyst and shows excellent functional-group tolerance.

Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis

A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.