Category: 1195-58-0

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Dihydropyridines. V. Formation of the isomeric 1,2- and 1,4-dihydro derivatives in the reaction of methylmagnesinm iodide with 3,5-dicyanopyridine and 3,5-dicyano-2-methylpyridine》. Authors are Kuthan, J.; Janeckova, E.; Havel, M..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Electric Literature of C7H3N3. Through the article, more information about this compound (cas:1195-58-0) is conveyed.

cf. CA 58, 5626a. MeMgI adds to 3,5-dicyanopyridine (I) to give 3,5-dicyano-2-methyl-1,2-dihydropyridine (II) and 3,5-dicyano-4-methyl-1,4-dihydropyridine (III). Similarly, 3,5-dicyano-2-methylpyridine (IV) forms 3,5-dicyano-2,6-dimethyl-1,2-dihydropyridine (V) and 3,5-dicyano-2,4-dimethyl-1,4-dihydropyridine (VI), resp. Nicotinoyl chloride-HCl (from 500 g. nicotinoic acid and 1400 ml. SOCl2) refluxed 35 hrs. with 500 ml. Br, the mixture evaporated on a steam bath, the residue dissolved in 1 l. absolute EtOH, and the solution heated 30 min. on a steam bath gave 81% HBr salt of Et 5-bromonicotinate, m. 147-7.5° (EtOH), from which 80% Et 5-bromonicotinate (VII), b0.5 86-92°, m. 42°, was obtained by treatment with Na2CO3. VII (50 g.) stirred with 30 g. CuCN in 50 ml. HCONMe2 2 hrs. at 160-75°, the mixt evaporated in vacuo, and the residue shaken with 500 ml. concentrated NH4OH and extracted successively with 800 ml. C6H6 and 200 ml. Et2O gave after evaporation 45% Et 5-cyanonicotinate (VIII), b16 143-5°, m. 89-90° (petr. ether). VIII (50 g.) in 1 l. absolute EtOH saturated with NH3 kept 7 days at room temperature gave 72% 5-cyanonicotinamide (IX), m. 220-1° (H2O, EtOH). A mixture of 14 g. IX and 40 ml. anhydrous C5H5N treated over 15 min. with 9 ml. POCl3, stirred 8 hrs., decomposed with ice, alkalized with NH4OH, and extracted with CHCl3 gave 64% I, m. 113-13.5° (dilute EtOH), sublimed 80-90°/10 mm. K salt of 2-hydroxy-3,5-dicyano-6-methylpyridine (6.07 g.) and 7 g. PCl5 treated with 10 ml. POCl3, and the mixture refluxed 30 min., evaporated in vacuo, decomposed with ice, and extracted with C6H6 gave 35% 3,5-dicyano-2-chloro-6-methylpyridine, m. 143-3.5°, which gave IV, m. 76-7°, on catalytic hydrogenation. Reaction of 1.04 g. I in 70 ml. Et2O with MeMgI (from 0.8 g. Mg, 2 ml. MeI, and 30 ml. Et2O) followed by chromatography on Al2O3 (activity II) gave 512 mg. yellow II, m. 114-15° (C6H6, dilute EtOH), and 240 mg. yellowish III, m. 180.5-81° (dilute EtOH). Similarly, 670 mg. IV with MeMgI (from 0.72 g. Mg, 1.9 ml. MeI, and 25 ml. Et2O) afforded 405 mg. yellow V, m. 152-3° (dilute MeOH), and 138 mg. yellowish VI, m. 129.5-30.5°. Dehydrogenation of II, III, V, and VI by heating with equal amounts 30% Pd-C 20 min. at 200-5° gave IV, 3,5-dicyano-4-methylpyridine, m. 84.5-85°, 3,5-dicyano-2,6-dimethylpyridine, m. 118-18.5°, and 3,5-dicyano-2,4-dimethylpyridine, m. 115-15.5°, resp. Ultraviolet and infrared data for II, III, V, and VI, and of some of the intermediates, are given.

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COA of Formula: C7H3N3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Oxidation of organic compounds. XCIV. Synthesis of 3,5-dicyanopyridine by the oxidative ammonolysis of 3,5-butidine. Author is Suvorov, B. V.; Kagarlitskii, A. D.; Belova, N. A.; Kutzhanov, R. T..

Ammoxidation of 3,5-lutidine (I) using 1:9:17 I-O-NH3 at 350° in the presence of fused vanadium oxide-titanium oxide with a 0.5 sec contact time gave 40% 3,5-pyridinedicarbonitrile (II) and 5-methyl-3-pyridinecarbonitrile. Hydrolysis of II in aqueous NaOH gave 3,5-pyridinedicarboxylic acid.

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SDS of cas: 1195-58-0. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Dihydropyridines. XV. Reactions of some 3,5-dicyanopyridines with complex aluminum hydrides. Author is Kuthan, Josef; Prochazkova, J.; Janeckova, E..

The effect of 4 complex Al hydrides on the formation of the 1,2- and 1,4-dihydro derivatives was studied. The reductions were carried out in tetrahydrofuran or Et2O and the products separated by thin layer chromatography (the starting compound I, reagent, % yield of the mixture, product(s), and their ratio given): I (R1 = R2 = H), LiAlH4, NaAlH4, NaAlH2(OEt)2, 41-98, II (R1 = R2 = H), III (R1 = R2 = H), 44-7: 53-6; I (R1 = R2 = H), NaAlH2(OCH2CH2OMe)2, 12, II (R1 = R2 = H), 100%; I (R1 = H, R2 = Me), LiAlH4, 36, III (R1 = H, R2 = Me), 100%; I (R1 = H, R2 = Et), LiAlH4, 25, II (R1 = H, R2 = Et), III (R1 = H, R2 = Et), 91:9; I (R1 = Me, R2 = H), LiAlH4, 80, II (R1 = Me, R2 = H), 100%; I (R1 = R2 = Me), LiAlH4, 65, II (R1 = R2 = Me), III (R1 = R2 = Me), 43:57; and I (R1 = Me, R2 = Et), LiAlH4, 48, II (R1 = Me, R2 = Et), III (R1 = Me, R2 = Et), 20:80.

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Quality Control of Pyridine-3,5-dicarbonitrile. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP. Author is Zhang, Xingjie; Xia, Aiyou; Chen, Haoyi; Liu, Yuanhong.

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.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Vapor-phase oxidation and oxidative ammonolysis of some alkylpyridines on a vanadium-iron catalyst, the main research direction is alkylpyridine oxidation ammonolysis iron vanadium catalyst; cyanopyridine.Recommanded Product: Pyridine-3,5-dicarbonitrile.

Optimum conditions were determined for gas-phase oxidation and oxidative ammonolysis for each of 4 alkylpyridines (2- and 3-picoline, 2-methyl-5-ethylpyridine, 3,5-lutidine) over the catalyst 2V2O5·Fe2O3 in the presence or absence of H2O. At best, overall selectivity for oxygen- and nitrogen-containing derivatives (e.g., cyanopyridines) of pyridine reached 80-90%.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Pyridine-3,5-dicarbonitrile(SMILESS: N#CC1=CC(C#N)=CN=C1,cas:1195-58-0) is researched.Reference of (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine. The article 《A study of solvent effect on photochemically induced reactions between pyridinedicarbonitriles and alkenes: an easy approach to the synthesis of cyclopenta[b or c]pyridines》 in relation to this compound, is published in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry. Let’s take a look at the latest research on this compound (cas:1195-58-0).

Photochem. induced reactions of pyridinedicarbonitriles and alkenes showed an interesting dependence on solvent polarity. In non-polar solvents ipso-substitution of the cyano groups in positions α or γ to the heterocyclic nitrogen occurred to a larger extent, while in polar solvents the reaction provided a path to the formation of a new ring between the carbon atom of one of the cyano groups and a ring position, forming a cyclopenta[b]pyridine or cyclopenta[c]pyridine derivatives Studies on the multiplicity of the excited state controlling the reaction showed that the singlet state was involved in the ipso-substitution, while the triplet state controlled the formation of the pyridine. An explanation for the solvent effect was given in terms of shift of the excited states with the solvent used. Theor. calculations justified the position of the cyclization, although no correlation was found for the regioisomers ratio. This reaction represented an effective entry to the biol. interesting pyrindine systems.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0 ) is researched.Synthetic Route of C7H3N3.Skala, Vratislav; Kuthan, Josef published the article 《Molecular orbital study of the NMR and electronic spectra of monocyanopyridines, dicyanopyridines, and 2,4,6-tricyanopyridine》 about this compound( cas:1195-58-0 ) in Collection of Czechoslovak Chemical Communications. Keywords: mol orbitals cyaonopyridines; cyanopyridines mol orbitals; orbitals mol cyanopyridines; NMR cyanopyridines; electronic spectra cyanopyridines. Let’s learn more about this compound (cas:1195-58-0).

The Hueckel MO and SCF methods gave identical results in the determination of quantum-chem. characteristics of 10 cyanopyridines. A good agreement between the exptl. absorption curves and electronic transitions, calculated by the limited configuration interaction (LCI) method, was obtained in the electronic spectra. In the PMR spectra, there was an improved correlation with the exptl. data in the use of the SCF method only in the case of chem. shifts and π-electron d. The application of the SCF orbitals in the place of Hueckel MO in the LCI calculation of the electronic spectra did not improve significantly the description of the π-electron structure of the compounds studied.

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He, Hongming; Sun, Fuxing; Zhao, Nian; Yuan, Rongrong; Zhu, Guangshan published the article 《Three novel zinc(II) metal-organic frameworks based on three tetrazolate ligands: synthesis, structures and photoluminescence》. Keywords: luminescence zinc phenylenetetrazole pyridinetetrazole imidazoletetrazole metal organic framework; crystal structure zinc phenylenetetrazole pyridinetetrazole imidazoletetrazole metal organic framework; mol structure zinc phenylenetetrazole pyridinetetrazole imidazoletetrazole metal organic framework; electrochem zinc phenylenetetrazole pyridinetetrazole imidazoletetrazole metal organic framework.They researched the compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0 ).COA of Formula: C7H3N3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1195-58-0) here.

Three metal-organic frameworks (MOFs), [Zn(BPT)H2O] (JUC-121), [Zn5(IBT)6]·8[H2NMe2]·DMA (JUC-122) and [Zn(TPD)(H2O)2]·0.5H2O (JUC-123) (JUC = Jilin University, China), H2BPT = (5-bromo-1,3-phenylene)bis(tetrazole), H3IBT = 4,5-bis(tetrazol-5-yl)imidazole and H2TPD = 3,5-di(tetrazol-5-yl)pyridine, were obtained by the reactions of Zn(NO3)2·6H2O and three tetrazolate ligands, which were characterized by single crystal x-ray diffraction, thermal gravimetric analyses (TGA), FTIR spectra (FTIR), elemental anal. (CHN) and powder X-ray diffraction (PXRD). From the crystal structures of these complexes and the coordination modes of the ligands, the authors can see that the tetrazolate ligands have multi-connectivity abilities to obtain intriguing varieties of mol. architectures. JUC-121 displays a three-dimensional (3D) network with the point symbol (4·65)2(42·84)(64·82). JUC-122 shows a two-dimensional (2D) framework with the point symbol (243)2(24)9 and JUC-123 has a 2-dimensional bimodal (3, 3)-connected net with the point symbol (4·82). The solid-state fluorescent spectra of JUC-121, JUC-122, JUC-123 and the free ligands were measured at room temperature

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Dihydropyridines. VII. Reactions of symmetrically alkylated 3,5-dicyanopyridines with sodium borohydride》. Authors are Kuthan, J.; Janeckova, E..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Electric Literature of C7H3N3. Through the article, more information about this compound (cas:1195-58-0) is conveyed.

cf. ibid. 1495; CA 60, 6817d. NaBH4 reduction of 3,5-dicyanopyridines I-VI gave 3,5-dicyano-1,2- and 1,4-dihydropyridines VII-XVII. I and LiAlH4 gave a mixture of VII and VIII which was separated by chromatography. Two procedures were used in the reduction of I-VI: Method A. EtOH (0.2 ml.) was added to a mixture of 38 mg. NaBH4 and 0.001 mole ground I-VI, and the precipitated product washed with 2.5 ml. cold H2O. Method B. NaBH4 (150 mg.) was added to a mixture of 0.002 mole I-VI and 5 ml. EtOH, the solution diluted with H2O to ∼80 ml. after several hrs., and the precipitated filtered off (starting compound, method, product, % yield, and m.p. given): I, B, VIII, 62, 205-6° (dilute EtOH); I, A, VII, 188-9° (Me2CO-cyclohexane) (VIII was also obtained); II, A, IX, 50, 214-15° (dilute EtOH); III, A, X + XI (92:8), 44, 154-72° (mixture); IV, B, XII, 89, 232-3° (MeOH); V, B, XIV + XV (71:29), 69, 138-69° (mixture); VI, -, XVI + XVII (86:14), 77, 108-22° (mixture). Similar results were obtained by reduction of I-IV with LiAlH4. Oxidation of 1.73 g. 3,5-dicyano-2-methyl-4-ethyl-1,2-dihydropyridine in 70 ml. EtOH with Ag2O from 7 g. AgNO3 gave 91% 3,5-dicyano-2-methyl-4-ethylpyridine (XVIII), m. 68-8.5°, sublimed 55-60°/0.4 mm. Treatment of 1.28 g. XVIII with MeMgI prepared from 750 mg. Mg and 1.9 ml. MeI gave 61% XVII, m. 101-2° (dilute acetone), which was oxidized with MnO2 to VI, m. 70-1°.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0 ) is researched.Safety of Pyridine-3,5-dicarbonitrile.Kuthan, J.; Musil, L.; Kohoutova, A. published the article 《Dihydropyridines. XXIV. Partial hydrogenation of some 3,5-dicyanopyridines》 about this compound( cas:1195-58-0 ) in Collection of Czechoslovak Chemical Communications. Keywords: pyridine dihydro dicyano. Let’s learn more about this compound (cas:1195-58-0).

Partial hydrogenation of 3,5-dicyanopyridine in EtOH over Pd on BaSO4 or BaCO3 gave a mixture of 3,5-dicyano-1,2-dihydropyridine and 3,5-dicyano-1,4-dihydropyridine. A similar hydrogenation of 3,5-dicyano-4-methylpyridine gave only the 1,2-dihydro derivative 3,5-Dicyano-2,6-dimethylpyridine and 3,5-dicyano-2,4,6-trimethylpyridine gave only traces of the 1,2- and 1,4-dihydro derivatives The mechanism of hydrogenation is discussed with the use of bicentric localization energies and simple Hueckel MO theory.

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