202003-06-3

Basic information

• Product Name: 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole
• Synonyms: 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole;4-cyano-1-(2,6-diflu;1-[(2,6-difluorophenyl)Methyl]-1H-1,2,3-triazole-4-carbonitrile;1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carbonitrile
• CAS NO: 202003-06-3
• Molecular Formula: C10H6F2N4
• Molecular Weight: 220.18
• Mol File: 202003-06-3.mol

Chemical Properties

• Boiling Point: 384.498 °C at 760 mmHg
• Flash Point: 186.338 °C
• Appearance: /
• Density: 1.381 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole(202003-06-3)
• EPA Substance Registry System: 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole(202003-06-3)

Safety Data

• Hazardous Substances Data: 202003-06-3(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Preparation:
4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole is used as a key intermediate in the preparation of allyl ruthenium hydroxyphosphine chloride, which serves as an efficient catalyst for the selective hydration of nitriles to amides in water under mild conditions. The unique electronic and steric properties of the 2,6-difluorobenzyl group in this triazole molecule contribute to the enhanced performance of the resulting catalyst.
In the Chemical Industry:
The compound 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole is used as a building block for the synthesis of various complex organic molecules, particularly those with potential applications in pharmaceuticals, agrochemicals, and materials science. Its unique structural features, including the triazole ring and the difluorobenzyl group, make it a valuable component in the design and synthesis of novel molecules with specific biological activities or material properties.
In the Pharmaceutical Industry:
4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole may also find applications in the pharmaceutical industry as a starting material for the development of new drugs. The triazole moiety is a common structural element in many biologically active compounds, and the presence of the difluorobenzyl group could provide additional opportunities for optimizing the pharmacokinetic and pharmacodynamic properties of drug candidates.
In the Agrochemical Industry:
Similarly, 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole could be utilized in the agrochemical industry for the development of new pesticides or other agrochemical products. The compound's unique structure may offer advantages in terms of selectivity, efficacy, and environmental impact when compared to existing products.

InChI:InChI=1/C10H6F2N4/c11-9-2-1-3-10(12)8(9)6-16-5-7(4-13)14-15-16/h1-3,5H,6H2

Upstream product

• 106308-60-5 2-(azidomethyl)-1,3-difluorobenzene 
• 142-82-5 n-heptane 
• 920-37-6 2-Chloroacrylonitrile 
• 85118-00-9 2,6-Difluorobenzyl bromide 
• 13648-23-2 methyl 3,5-dichloro-2,4,6-trifluorobenzoate 
• 13671-00-6 methyl 2,6-difluorobenzoate 
• 19064-18-7 2,6-difluorobenzyl alcohol 

Downstream Products

• 106308-44-5 rufinamide 

Relevant articles and documents

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Hemilability-Driven Water Activation: A NiII Catalyst for Base-Free Hydration of Nitriles to Amides

The NiII complex 1 containing pyridyl- and hydroxy-functionalized N-heterocyclic carbenes (NHCs) is synthesized and its catalytic utility for the selective nitrile hydration to the corresponding amide under base-free conditions is evaluated. The title compound exploits a hemilabile pyridyl unit to interact with a catalytically relevant water molecule through hydrogen-bonding and promotes a nucleophilic water attack to the nitrile. A wide variety of nitriles is hydrated to the corresponding amides including the pharmaceutical drugs rufinamide, Rifater, and piracetam. Synthetically challenging α-hydroxyamides are accessed from cyanohydrins under neutral conditions. Related catalysts that lack the pyridyl unit (i.e., compounds 2 and 4) are not active whereas those containing both the pyridyl and the hydroxy or only the pyridyl pendant (i.e., compounds 1 and 3) show substantial activity. The linkage isomer 1′ where the hydroxy group is bound to the metal instead of the pyridyl group was isolated under different crystallization conditions insinuating a ligand hemilabile behavior. Additional pKa measurements reveal an accessible pyridyl unit under the catalytic conditions. Kinetic studies support a ligand-promoted nucleophilic water addition to a metal-bound nitrile group. This work reports a Ni-based catalyst that exhibits functional hemilability for hydration chemistry.

Process for preparing 1-substituted 4-cyano-1,2,3-triazoles

PCT No. PCT/EP97/03671 Sec. 371 Date Jan. 8, 1999 Sec. 102(e) Date Jan. 8, 1999 PCT Filed Jul. 10, 1997 PCT Pub. No. WO98/02423 PCT Pub. Date Jan. 22, 1998The invention relates on the one hand to a novel preparation of compounds of the formula (I) in whic