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Usage

Uses

Used in Organic Synthesis:
1-(cyanomethyl)triaza-1,2-dien-2-ium is used as a reactant in various organic synthesis reactions due to its strong electrophilicity. Its reactivity allows it to participate in the formation of new chemical bonds, making it a valuable component in creating a wide range of organic compounds.
Used as an Intermediate in Heterocyclic Compounds and Pharmaceuticals Synthesis:
In the pharmaceutical and chemical industries, 1-(cyanomethyl)triaza-1,2-dien-2-ium is utilized as an intermediate. Its unique structure and reactivity make it instrumental in the synthesis of heterocyclic compounds and various pharmaceuticals, contributing to the development of new drugs and chemical products.
Used in Catalytic Applications:
1-(cyanomethyl)triaza-1,2-dien-2-ium has also been studied for its potential use in catalysis. Its ability to form temporary bonds with reactants can facilitate certain chemical reactions, making it a candidate for use in catalytic processes that require strong electrophiles.
Used as a Reagent in the Development of New Organic Reactions:
Due to its highly reactive nature, 1-(cyanomethyl)triaza-1,2-dien-2-ium serves as a reagent in the research and development of new organic reactions. Its involvement can lead to the discovery of innovative synthetic pathways and methodologies in organic chemistry.

Upstream product

• 107-14-2 chloroacetonitrile 
• 590-17-0 cyanomethyl bromide 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 13838-08-9 Azidamfenicol 
• 74-90-8 hydrogen cyanide 
• 1197884-57-3 tert-butyl 3-{2-[1-(cyanomethyl)-1H-1,2,3-triazol-4-yl]-1-[(4-methylphenyl)sulfonyl]ethyl}-1H-indole-1-carboxylate 
• 757995-76-9 4-(5-phenyltetrazol-2-ylmethyl)-1,2,3-triazol-1-ylacetonitrile 
• 69067-19-2 (triphenylphosphoranylidene)aminoacetonitrile 
• 117949-36-7 (5-Phenyl-[1,2,3,4]triazaphosphol-3-yl)-acetonitrile 

Relevant academic research and scientific papers

Synthesis of polycyclic functionally-substituted triazole- and tetrazole-containing systems

Cycloaddition of organic mono- and diazides to the triple bond of propargyl esters of mono- and dicarboxylic acids gave rise to polycyclic 1,2,3-triazole-substituted carboxylates. Dipropargyl dicarboxylates with diazides afforded oligomeric products with

Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and 'click' strategy

Abstract To develop more effective antitumor steroidal drugs, we synthesized a library including twenty-two novel cytotoxic 2-alkyloxyl substituted (25R)-spirostan-1,4,6-triene-3-ones and corresponding 1,2,3-triazoles through an abnormal monoepoxide ring-opening/elimination and 'click' reactions. After the cytotoxic evaluations against HepG2, Caski and HeLa cell lines, three steroidal triazoles 5b, 5f and 5m in this library were found to possess potent anti-proliferative effects against Caski cells with the half-inhibitory concentrations (IC50) of 9.4-11.8 μM. The high-efficient and straightforward process was attractive feature for facile preparation of anti-tumor steroidal triazoles.

Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation

A general method for the synthesis of a library of hitherto unreported amino-1,4-naphthoquinone-appended triazoles was accomplished via a sequential three-component reaction of substituted N-propargylaminonaphthoquinones with variously substituted alkyl bromides/2-bromonaphthalene-1,4-dione and sodium azide in the presence of Et3N/CuI in water. Aminonaphthoquinone- appended iminochromene-triazole hybrid heterocycles were also synthesized from the amino-1,4-naphthoquinone-appended-1,2,3-triazolylacetonitriles. All the triazole hybrids were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB). Among the triazoles, 2-(((1-benzyl-1H-1,2, 3-triazol-4-yl)methyl)(4-(trifluoromethyl)phenyl)amino)naphthalene-1,4-dione (7d) emerged as the most active one with IC50 = 1.87 μM, being more potent than the anti-TB drugs, cycloserine (6 times), pyrimethamine (20 times) and equipotent as the drug ethambutol (IC50 1.56 μM).

One-pot synthesis of 3-triazolyl-2-iminochromenes via a catalytic three component cascade reaction

A variety of 3-triazolyl-2-iminochromenes were synthesized in a one-pot, catalytic, three component condensation. In this event, a Cu(I)-catalyzed cycloaddition between 2-azidoacetonitrile and an acetylene formed a triazole and activated the neighboring methylene group, inducing an aldol-cyclization- dehydration sequence in the presence of a salicylaldehyde. Further elaboration led to more complex polyheterocycles.

Novel 1,3-alternate thiacalix[4]arenes: Click synthesis, silver ion binding and self-assembly

A series of novel 1,3-alternate thiacalixarene derivatives containing triazole groups were synthesized directly from a conformationally mixed intermediate in high yields using click chemistry. They were used as building blocks for supramolecular self-assembly architecture, and shown to be good Ag+ receptors. As confirmed by AFM, one of the compounds was found to form nanorod aggregates by silver ion binding. The Royal Society of Chemistry 2013.

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

Synthesis of polynuclear nonfused azoles

Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well

Organic Azides. 3. Ultrasound Synthesis of Propargyl Azide, Azidoacetonitrile and Primary Allylic Azides

The title azides were prepared from the corresponding activated primary halides and aqueous sodium azide under ultrasonic irradiation.

REACTION OF TRIMETHYLSILYL AZIDE WITH ORGANIC HALIDES

Trimethylsilyl azide reacted readily with benzyl, allyl, and aliphatic halides to give the corresponding azides in good to excellent yields.