1195-58-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dicyano pyridine is used as a building block for the synthesis of various pharmaceuticals due to its versatile reactivity and ability to form a wide range of compounds with potential therapeutic properties.
Used in Agrochemical Industry:
3,5-Dicyano pyridine is used as a key intermediate in the production of pesticides, contributing to the development of effective crop protection agents.
Used in Organic Synthesis:
3,5-Dicyano pyridine is used as a versatile reagent in the synthesis of heterocycles, which are important structural motifs in many biologically active compounds and materials.
Used in Dye Industry:
3,5-Dicyano pyridine is used in the synthesis of dyes, taking advantage of its ability to form colored compounds with specific properties for various applications.
Used in Coordination Chemistry:
3,5-Dicyano pyridine is used as a ligand, playing a crucial role in the formation and stabilization of metal complexes with potential applications in catalysis, sensing, and materials science.
Used in Catalyst Industry:
3,5-Dicyano pyridine is used as a catalyst in various reactions, promoting the conversion of reactants to products with improved efficiency and selectivity.
Used in Vitamin B6 Production:
3,5-Dicyano pyridine is used as a precursor in the manufacturing of 3-cyano pyridine, which is an essential compound in the synthesis of vitamin B6, an essential nutrient for human health.

InChI:InChI=1/C7H3N3/c8-2-6-1-7(3-9)5-10-4-6/h1,4-5H

Upstream product

• 4663-99-4 pyridine-3,5-dicarboxamide 
• 557-21-1 zinc(II) cyanide 
• 2457-47-8 3,5-dichloropyridine 
• 499-81-0 3,5-Pyridinedicarboxylic acid 
• 591-22-0 3,5-Lutidine 
• 1539-48-6 2,4,6-trimethylpyridine-3,5-dicarbonitrile 

Downstream Products

• 280-74-0 3,7-diazabicyclo{3.3.1}nonane 
• 146073-63-4 2,6-di(1-adamantyl)pyridine-3,5-dicarbonitrile 
• 146073-61-2 2-isopropylpyridine-3,5-dicarbonitrile 
• 1221430-89-2 5-(4-amino-6-benzyl-thieno[2,3-d]pyrimidin-2-yl)nicotinonitrile 

Relevant academic research and scientific papers

Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound

The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations

A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ red > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.

Process for preparing nitriles

A heteroaromatic nitrile is prepared in a high selectivity and yield by catalytically reacting an alkyl-substituted heteroaromatic compound with molecular oxygen and ammonia in a molar ratio of oxygen to ammonia of not larger than 1.6:1 in a gaseous phase in the presence of a catalyst comprising a vanadium-phosphorus oxide of the formula: wherein x, y and z represent atomic ratios of phosphorus, antimony and oxygen to vanadium, respectively, and x is from 0.1 to 5, y is 0 to 8 and z is defined from the valencies of other elements.