Category: nitriles-buliding-blocks

Wu, Ao-rong published the artcileSynthesis of aromatic acyl cyanides catalyzed by Sm(OTf)₃, COA of Formula: C8H6ClN, the publication is Nongyao (2013), 52(4), 241-243, 246, database is CAplus.

The paper aimed to study a new synthetic method of aromatic acyl cyanides. Catalyzed by samarium triflate [Sm(OTf)₃] aromatic acyl chlorides was reacted with sodium cyanide to give aromatic acyl cyanides. Under the optimal reaction conditions, the yields and purities of aromatic acyl products reached about 90% and above 98% resp. It was a novel practical method to prepare aromatic acyl cyanides, with mild reaction conditions and high selectivity, and without the use of phase transfer catalyst.

Nongyao 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 C23H23ClN2O4, COA of Formula: C8H6ClN.

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

Makida, Yusuke published the artcileNickel-catalysed carboxylation of organoboronates, Related Products of nitriles-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(59), 8010-8013, database is CAplus and MEDLINE.

A nickel/N-heterocyclic carbene (NHC) catalyzed carboxylation of aryl-, heteroaryl- and alkenylboronates, affording the corresponding carboxylic acids, has been developed. This transformation proceeds under one atm. of CO₂ with a broad range of substrates and exhibits good functional group compatibility.

Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Related Products of nitriles-buliding-blocks.

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

Motiyenko, Roman A. published the artcileHigh-Resolution Millimeter Wave Spectroscopy and Ab Initio Calculations of Aminomalononitrile, Application In Synthesis of 5098-14-6, the publication is Journal of Physical Chemistry A (2015), 119(6), 1048-1054, database is CAplus and MEDLINE.

The HCN trimer aminomalononitrile (H₂NCH(CN)₂, AMN) is considered as a key compound in prebiotic chem. and a potential candidate for detection in the interstellar medium. In this view, we studied the rotational spectrum of AMN in the 120-245 GHz frequency range. The spectroscopic work was augmented by high-level ab initio calculations The calculations showed that between two existing rotamers, sym. and asym., the most stable is the asym. conformation, and it is the only conformation observed in the recorded spectra. The sym. conformation is 6.7 kJ/mol higher in energy and thus has a very low Boltzmann factor. The anal. of the rotational spectra of the A conformation has shown that the observed lines exhibit a doublet or quartet structure owing to two large-amplitude motions, C-N torsion and amino group inversion. To study the large-amplitude motions in detail, we calculated a two-dimensional potential energy surface and determined the barrier heights for the torsion and inversion, V_t = 12.5 kJ/mol and V_i = 19.1 kJ/mol. About 2500 assigned rotational transitions in the ground vibrational state were fitted within exptl. accuracy using the reduced axes system Hamiltonian. The set of obtained spectroscopic parameters allows accurate calculation of transition frequencies and intensities for an astrophys. search of AMN.

Journal of Physical Chemistry A 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, Application In Synthesis of 5098-14-6.

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

Zhang, Yan published the artcileThe photochromic behaviour of two viologen salts modulated by the distances between the halide anions and the cationic N atoms of viologen, COA of Formula: C8H6ClN, the publication is Acta Crystallographica, Section C: Structural Chemistry (2019), 75(12), 1628-1634, database is CAplus and MEDLINE.

In recent years, viologens and their derivatives have received much attention due to their various potential applications, ranging from electro- or photochromic devices to clean energy. Generally, viologen compounds exhibit a color change upon being subjected to an external stimulus. However, the chromic mechanism is still ambiguous, because there are many electron-transfer pathways for a chromic compound that need to be considered. Thus, exploring new chromic viologen-based compounds with one pathway should be important and meaningful. In this article, two new viologen-based derivatives, namely 1-(2-cyanobenzyl)-4,4′-bipyridinium chloride (o-CBbpy·Cl), C₁₈H₁₄N₃⁺·Cl^– (1), and 1-(2-cyanobenzyl)-4,4′-bipyridinium bromide (o-CBbpy·Br), C₁₈H₁₄N₃⁺·Br^– (2), have been synthesized and characterized. Interestingly, both isomorphic compounds possess only one electron-transfer pathway, in which 1-(2-cyanobenzyl)-4,4′-bipyridinium cations (o-CBbpy) and halide anions are employed as electron donors and acceptors, resp. Salts 1 and 2 consist of o-CBbpy cations involved in p-p interactions and hydrogen-bond interactions, and halide anions weakly hydrogen bonded to the viologen cations. The salts show different photoresponsive characteristics under identical conditions, which should be mainly related to the distances between the halide cations and the cationic N atoms of o-CBbpy but not the electronegativities of the halogen atoms. These results should not only help in understanding that the distance of the electron-transfer pathway plays an important role in viologen-based photochromism, but should also guide the design and synthesis of addnl. photochromic materials.

Acta Crystallographica, Section C: Structural Chemistry 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 C18H28B2O4, COA of Formula: C8H6ClN.

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

Huang, Ping published the artcileSilver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes with CF₃SO₂Na, Quality Control of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(42), 4705-4708, database is CAplus.

A novel and convenient approach to the synthesis of substituted β-trifluoromethyl styrenes (E)-RCH=CHCF₃ (R = 2,4-Cl₂C₆H₃, 4-O₂NC₆H₄, naphthalen-2-yl, etc.) via a silver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes (E)-RCH=CHNO₂ with CF₃SO₂Na under relatively mild conditions has been developed. This protocol delivered excellent stereoselectivity and showed wide substrate tolerance.

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, Quality Control of 5153-73-1.

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

Liu, Dong published the artcileNickel-Catalyzed Selective Oxidative Radical Cross-Coupling: An Effective Strategy for Inert Csp³-H Functionalization, COA of Formula: C12H14BNO2, the publication is Organic Letters (2015), 17(4), 998-1001, database is CAplus and MEDLINE.

An effective strategy for inert Csp³-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated [e.g., PhB(OH)₂ + cyclohexane â†?phenylcyclohexane (73%) in presence of Ni(acac)₂, Ph₃P, dppb, K₃PO₄ as base, and di-tert-Bu peroxide as oxidant]. D. functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp³-H arylation products in good yields.

Organic Letters published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, COA of Formula: C12H14BNO2.

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

Li, Qing-Hua published the artcileTitanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia, Formula: C8H6ClNO, the publication is Organic Letters (2019), 21(20), 8429-8433, database is CAplus and MEDLINE.

Herein, the direct amination of cyanohydrins with the partner of ammonia for the synthesis of N-unprotected α-aminonitriles H₂NC(R¹)(R²)CN (R¹ = Ph, 4-FC₆H₄, 2-thienyl, etc.; R² = H, Me, Et; -R¹R²– = -(CH₂)₄-) is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesized with moderate to high yields under mild reaction conditions.

Organic Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Formula: C8H6ClNO.

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

Liu, Tang-Lin published the artcileCyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 651-654, database is CAplus and MEDLINE.

In the presence of Ti(Oi-Pr)₄, aldehyde and ketone cyanohydrins underwent amination reactions with amines such as 4-methoxyaniline to yield α-aminonitriles. Aryl, aryl alkyl, and dialkyl ketones and aryl and alkyl aldehyde cyanohydrins underwent amination. Reaction of aldehyde cyanohydrins with 4-methoxyaniline in the presence of Ti(Oi-Pr)₄, (S)-BINOL, and quinine yielded nonracemic (S)-α-aminonitriles in 31-88% ee. The reaction mechanism was studied; the reaction is proposed to occur by elimination of cyanide from the cyanohydrin followed by imine formation and addition of cyanide to the imine (“cyanide borrowing”) rather than by loss of a proton, imine formation, and reduction (“hydrogen borrowing”).

Chemical Communications (Cambridge, United Kingdom) published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Liu, Yan-Kai published the artcileOpen-Close: An Alternative Strategy to α-Functionalization of Lactone via Enamine Catalysis in One Pot under Mild Conditions, Formula: C9H6N2O2, the publication is Organic Letters (2015), 17(8), 2022-2025, database is CAplus and MEDLINE.

An open-close strategy in asym. catalysis is newly developed. With this powerful strategy, lactols are directly applied as potential precursors of lactones in enamine-based asym. Michael reactions providing a facile access to α-functionalized lactones containing two adjacent stereogenic centers as a single diastereomer, e.g. I, in good to excellent yields (up to 99%) and with excellent enantioselectivities (most cases >99%). Moreover, the reaction products are shown to give highly functionalized derivatives by stepwise systematic transformations.

Organic 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, Formula: C9H6N2O2.

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

Chen, Wen-Hsuan published the artcileOne-Step Aminomalononitrile-Based Coatings Containing Zwitterionic Copolymers for the Reduction of Biofouling and the Foreign Body Response, Category: nitriles-buliding-blocks, the publication is ACS Biomaterials Science & Engineering (2019), 5(12), 6454-6462, database is CAplus and MEDLINE.

Many biomedical devices benefit from antibiofouling coatings, which can reduce biointerfacial interactions such as protein adsorption and cell attachment. In this study, we synthesized zwitterionic copolymers consisting of sulfobetaine methacrylate (SB) and 2-aminoethyl methacrylate (AE) via free radical polymerization and combined these copolymers in solution with aminomalononitrile to form zwitterionic coatings in an autopolymn. process. The successful deposition of coatings containing different SB/AE ratios was demonstrated by XPS. The one-step surface modification process was carried out on polydimethylsiloxane (PDMS), tissue culture polystyrene, and gold substrates, demonstrating that this method can be transferred to different substrate materials. The ability of optimized coatings to reduce serum protein adsorption was demonstrated by quartz crystal microbalance measurements while the ability to resist cell attachment for 24 h was demonstrated using L929 mouse fibroblasts. The stability of the coatings under physiol. conditions was investigated, and resistance to cell attachment was maintained over a period of 45 days. Furthermore, the resistance of the copolymer coating to cell attachment was maintained after both ethylene oxide sterilization and autoclaving. Finally, copolymer-modified PDMS samples were investigated with regard to their ability to reduce the foreign body response in vivo. Here, a significant reduction in the capsule thickness (approx. 50%) was observed in nude mice after 2 and 4 wk. It is expected that the one-step, facile, and versatile surface modification strategy discussed here will find applications in biomedical devices.

ACS Biomaterials Science & Engineering 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, Category: nitriles-buliding-blocks.

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