Category: nitriles-buliding-blocks

Kashanna, Jajula published the artcilePalladium catalyzed carboannulation of nitrostyrenes with internal alkynes: a new synthetic strategy for cross coupling/C-H annulation and facile access to indenones, Application In Synthesis of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(14), 1576-1581, database is CAplus.

Palladium(II) catalyzed carboannulation reaction of internal alkynes with nitrostyrenes to afford 2,3-disubstituted indenones is reported. The annulation reaction proceeds through transmetalation of Pd(II) with aldehydes generated from the nitrostyrene (C-H activation) and insertion of the alkynes, followed by cyclization via intramol. nucleophilic addition of intermediate organopalladium(II) species. This reaction proceeded in moderate to good yields and with high regioselectivity. Electron-rich nitrostyrenes were transformed to the corresponding aldehydes in high yields without addition of any peroxide reagent.

Tetrahedron Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Application In Synthesis of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kiyokawa, Kensuke published the artcileStraightforward Synthesis of 1,2-Dicyanoalkanes from Nitroalkenes and Silyl Cyanide Mediated by Tetrabutylammonium Fluoride, Computed Properties of 5153-73-1, the publication is Chemistry – A European Journal (2015), 21(3), 1280-1285, database is CAplus and MEDLINE.

A straightforward synthesis of 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN [R = 4-OCH₃C₆H₄, thiophen-2-yl, pyridin-3-yl, etc.; R¹ = H; RR¹ = (CH₂)₄] by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride was described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride was essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol was applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN.

Chemistry – A European Journal published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ieda, Naoya published the artcileDevelopment of photoredox-reaction-driven NO-releasing reagents and application for photomanipulation of vasodilation, Application In Synthesis of 26187-28-0, the publication is Yuki Gosei Kagaku Kyokaishi (2020), 78(11), 1048-1057, database is CAplus.

Nitric oxide (NO) is a signaling mol. that mediates vasodilation, neurotransmission, and immune response. Due to its instability in biol. environments, NO-releasing small-mol. compounds have been developed for biol. experiments and also as therapeutic reagents for vascular diseases. Although photocontrollable NO releasers are very useful chem. tools because of their precise operability in response to light irradiation, their biol. applications have been limited, mainly because they require UV light irradiation or contain metal ions with the potential to cause cytotoxicity. In order to overcome these problems, our group has developed visible-light-responsive NO releasers based on photoreodox reaction. These compounds are composed of two moieties, an NO-releasing moiety and a light-harvesting antenna moiety. After photoirradiation, photoinduced electron transfer from the NO releasing moiety to the antenna takes place, followed by NO release. Based on this system, we developed a blue-light-controllable NO releaser and a yellowish-green-light-controllable one, which are applicable for cellular and ex vivo experiments This account focuses on recent developments in photoredox-driven NO releasers and their applications for spatiotemporally controlled NO release in cells and ex vivo.

Yuki Gosei Kagaku Kyokaishi published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Application In Synthesis of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shie, Jiun-Jie published the artcileAn Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation, Quality Control of 26187-28-0, the publication is Journal of the American Chemical Society (2014), 136(28), 9953-9961, database is CAplus and MEDLINE.

The authors have designed a low fluorescent azido-BODIPY-based probe AzBOCEt (Az10) that undergoes copper(I)-catalyzed 1,3-dipolar cycloadditions with alkynes to yield strongly fluorescent triazole derivatives The fluorescent quantum yield of a triazole product T10 is enhanced by 52-fold as compared to AzBOCEt upon excitation at a wavelength >500 nm. Quantum mech. calculations indicate that the increase in fluorescence upon triazole formation is due to the lowering of the HOMO energy level of the aryl moiety to reduce the process of acceptor photoinduced electron transfer. AzBOCEt is shown to label alkyne-functionalized proteins in vitro and glycoproteins in cells with excellent selectivity, and enables cell imaging and visualization of glycoconjugates in alkynyl-saccharide-treated cells at extremely low concentration (0.1 μM). Furthermore, the alkyne-tagged glycoproteins from cell lysates can be directly detected with AzBOCEt in gel electrophoresis.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C8H6ClF3, Quality Control of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xia, Dao-Cheng published the artcileCrystal structure of bis([3,2-c]isoquinolin-5-amine)benzofuro[6,5-b]furancadmium(II) dichloride, Cd(C₂₄H₁₄N₄O₂)Cl₂, COA of Formula: C8H6ClN, the publication is Zeitschrift fuer Kristallographie – New Crystal Structures (2010), 225(3), 563-564, database is CAplus.

Crystal data: monoclinic, C2/c, a = 15.9926(9), b = 10.2755(4), c = 12.5031(5) Å, β = 94.725(4)°, Z = 4, 1500 observed reflections with I > 2(I), 150 refined parameters, R_gt(F) = 0.030, wR_ref(F²) = 0.055. At. coordinates are given. The structure is discussed.

Zeitschrift fuer Kristallographie – New Crystal Structures published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C24H26ClNO4, COA of Formula: C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Li, Pengyu published the artcileCopper(II)-Schiff Base Complex-Functionalized Polyacrylonitrile Fiber as a Green Efficient Heterogeneous Catalyst for One-Pot Multicomponent Syntheses of 1,2,3-Triazoles and Propargylamines, Name: 2-(Chloromethyl)benzonitrile, the publication is Advanced Synthesis & Catalysis (2018), 360(8), 1673-1684, database is CAplus.

A series of copper(II)-Schiff bases-functionalized polyacrylonitrile fiber catalysts was successfully prepared using copper acetate as copper source and characterized by elemental anal., Fourier-transfer IR spectroscopy, UV-visible spectroscopy, XPS and inductively coupled plasma anal. Excellent phys. strength and thermal stability of the fiber catalysts were demonstrated by SEM, X-ray diffraction, thermogravimetric/differential scanning calorimetry anal. and mech. strength measurements. Furthermore, these catalysts were successfully applied to one-pot multicomponent copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and aldehyde, alkyne, amine (A3) coupling reaction in which the influence of different substituent groups on the catalytic activities of fiber catalysts were investigated in detail. Among them, the bis[N-ethyl-3,5-di-tert-butyl-salicylideneiminato]copper(II)-functionalized polyacrylonitrile fiber (PANS₂F-Cu) as a green, efficient catalyst exhibited the best catalytic activity as its high hydrophobic micro-environment could aggregate the reactants to the catalytic sites and accelerate the reaction. In addition, the PAN_S2F-Cu performed well in scaled-up experiment and showed excellent recyclability (at least ten times), and these characteristics enabled it to have great potential for further applications.

Advanced Synthesis & Catalysis published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Tan, Emily H. P. published the artcile[(RCN)₂PdCl₂]-Catalyzed E/Z Isomerization of Alkenes: A Non-Hydride Binuclear Addition-Elimination Pathway, Product Details of C10H12F6N4O6PdS2, the publication is Angewandte Chemie, International Edition (2011), 50(41), 9602-9606, S9602/1-S9602/43, database is CAplus and MEDLINE.

[(RCN)₂PdCl₂] complexes efficiently catalyze double-bond migration and geometric E/Z interconversion in alkenes. We propose a new addition-elimination mechanism with a binuclear Pd species that selectively effects E/Z interconversion.

Angewandte Chemie, International Edition published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C9H9F5Si, Product Details of C10H12F6N4O6PdS2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Evans, Richard A. published the artcileHCN dimers: iminoacetonitrile and N-cyanomethanimine, Computed Properties of 5098-14-6, the publication is Journal of the American Chemical Society (1991), 113(19), 7261-76, database is CAplus.

Iminoacetonitrile H(NC)C:NH (I) has been prepared by two methods: (i) thermal decomposition of the tosylhydrazone salts H₂N(NC)C:NN^–TosM⁺ (Tos = tosyl, M = Na, Li) at 200° and (ii) Ar matrix photolysis of azidoacetonitrile. Ab initio calculations indicate that Z–I is of slightly lower energy than E–I, and this is confirmed by the IR spectra with use of the thermal methods. E–I/Z–I undergo photochem. interconversion, giving a ca. 3:1 photostationary E:Z ratio. E–I and Z–I are fully characterized by their gas-phase, matrix, and thin-film IR spectra, which are in excellent agreement with ab initio calculations, by ¹H and ¹³C NMR spectroscopy in solution, and by mass spectrometry. I polymerizes in solution above -40°; pyrolysis produces HCN, and matrix photolysis produces HNC and van der Waals complexes containing HNC. N–tert-Butyliminoacetonitrile thermally fragments to tert-Bu isocyanide and HCN. N-Cyanomethanimine H₂C:NCN (II) has also been prepared by two methods: (i) pyrolysis of trimethylenetetrazole (III) at 500-800° and (ii) pyrolysis of ditetrazolopyrazine (IV) at 600-850°. Both methods are extremely clean. II is fully characterized by its IR spectrum in agreement with ab initio calculations and, in conjunction with other work, by its mass and millimeter-wave spectra. II is thermodynamically stable in the gas phase up to ca. 800° at low pressure and short contact times but polymerizes in the solid state above -100°.

Journal of the American Chemical Society published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Computed Properties of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Zhang, Song published the artcileAsymmetric C-H arylation for synthesis of planar chiral ferrocenes: controlling enantioselectivity using chiral phosphoric acids, Synthetic Route of 68569-14-2, the publication is Youji Huaxue (2016), 36(4), 752-759, database is CAplus.

Transition-metal-catalyzed direct activation reactions of unreactive C-H bond has been extensively developed in recent years. Although numerous synthetic methods have been reported to build diverse complex compounds, enantioselective C-H activation has not been paid much attention to probably because of the absence of suitable ligands to control the stereoselectivity in the C-H activation reaction. Herein, a Pd(0)-catalyzed enantioselective synthesis of planar chiral ferrocenes was described, and chiral phosphoric acids were used as the only chiral source to control the stereoselectivity in the C-H activation reactions.

Youji Huaxue published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C13H16O2, Synthetic Route of 68569-14-2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Li, Feng published the artcileSynthesis of ethyl 4-cyanotetrahydropyran-4-carboxylate via solid-liquid phase transfer catalysis, Application of Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, the publication is Jingxi Huagong (2008), 25(6), 614-617, database is CAplus.

Eethyl 4-cyanotetrahydropyran-4-carboxylate was synthesized from di-(β-chloroethyl) ether, Et cyanoacetate and K₂CO₃ via solid-liquid phase transfer catalysis, using DMF as solvent and dodecyltrimethylammonium bromide (DTMAB) as catalyst [n(DTMAB):n(Et cyanoacetate) = 0.05:1]. The water produced was separated, sp. surface area of potassium carbonate was 6.72 × 10⁴ m^-1 and reaction temperature was 153°, the yield was 90.6%, the reaction time was 2 h. The mechanism and kinetics of the reaction were also studied. The reaction could be described by the pseudo-second-order kinetics. With DTMAB, CTMAB, TBAB and BETAC as catalysts, K_app were 0.01336, 0.01158, 0.00343. and 0.001738 L/(mol/min) respctively. The activation energy of di-(β-chloroethyl) ether and Et cyanoacetate was 58.94 kJ/mol.

Jingxi Huagong published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Application of Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts