Category: nitriles-buliding-blocks

Ludwig, Jacob R. published the artcileCobalt-Catalyzed C(sp²)-C(sp³) Suzuki-Miyaura Cross Coupling, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Organic Letters (2021), 23(3), 625-630, database is CAplus and MEDLINE.

A cobalt-catalyzed method for the C(sp²)-C(sp³) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N’-dimethylcyclohexane-1,2-diamine (DMCyDA, L¹) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

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, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Kumar, Saurabh published the artcileAIBN-Initiated Denitrative Cross-Coupling Reactions of β-Nitrostyrenes with Sulfonyl Hydrazides/Disulfides: A Metal-free Approach towards Vinyl Sulfones, Computed Properties of 5153-73-1, the publication is Asian Journal of Organic Chemistry (2018), 7(2), 359-362, database is CAplus.

A practical and metal free approach involving denitrative coupling of β-nitrostyrenes and sulfonyl hydrazides/disulfides by AIBN (azobisisobutyronitrile) was developed to accomplish the synthesis of vinyl sulfones I [R = Ph, 4-ClC₆H₄, 2-thienyl, etc.; R¹ = 4-MeC₆H₄, Bn, 2-naphthyl, etc.]. The method employed easily accessible starting materials and was endowed with a broad substrate scope, functional group tolerance and high yields.

Asian Journal of Organic Chemistry 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

Ambala, Srinivas published the artcileMetal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins, Quality Control of 5153-73-1, the publication is RSC Advances (2019), 9(52), 30428-30431, database is CAplus and MEDLINE.

A simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K₂S₂O₈) under an open atm. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and gave corresponding nitroolefins with good to excellent yields.

RSC Advances 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

Janssen-Mueller, Daniel published the artcileAnnulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones, Safety of 2-(Chloromethyl)benzonitrile, the publication is Organic Letters (2016), 18(17), 4444-4447, database is CAplus and MEDLINE.

The activation of 2-(bromomethyl)benzaldehydes using N-heterocyclic carbenes represents a novel approach to the generation of o-quinodimethane (o-QDM) intermediates. Coupling with ketones such as phenylglyoxylates, isatins, or trifluoromethyl ketones via [4 + 2] annulation gives access to functionalized 1-isochromanones.

Organic Letters 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, Safety of 2-(Chloromethyl)benzonitrile.

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

Peschiulli, Aldo published the artcileRuthenium-Catalyzed α-(Hetero)Arylation of Saturated Cyclic Amines: Reaction Scope and Mechanism, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Chemistry – A European Journal (2013), 19(31), 10378-10387, database is CAplus and MEDLINE.

Transition-metal-catalyzed sp³ C-H activation has emerged as a powerful approach to functionalize saturated cyclic amines. Our group recently disclosed a direct catalytic arylation reaction of piperidines at the α position to the nitrogen atom. 1-(Pyridin-2-yl)piperidine could be smoothly α-arylated if treated with an arylboronic ester in the presence of a catalytic amount of [Ru₃(CO)₁₂] and one equivalent of 3-ethyl-3-pentanol. A systematic study on the substrate and reagent scope of this transformation is disclosed in this paper. The effect of substitution on both the piperidine ring and the arylboronic ester has been investigated. Smaller (pyrrolidine) and larger (azepane) saturated ring systems, as well as benzoannulated derivatives, were found to be compatible substrates with the α-arylation protocol. The successful use of a variety of heteroarylboronic esters as coupling partners further proved the power of this direct functionalization method. Mechanistic studies have allowed for a better understanding of the catalytic cycle of this remarkable transformation featuring an unprecedented direct transmetalation on a Ru^II-H species.

Chemistry – A European Journal 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, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Song, Bok Joo published the artcileA Desirable Hole-Conducting Coadsorbent for Highly Efficient Dye-Sensitized Solar Cells through an Organic Redox Cascade Strategy, Related Products of nitriles-buliding-blocks, the publication is Chemistry – A European Journal (2011), 17(40), 11115-11121, S11115/1-S11115/10, database is CAplus and MEDLINE.

This hole-conducting co-adsorbent (HC-A) has multiple functions: a light-harvesting function as a short-wavelength light absorption dye mol. to increase J_sc, a prevention effect of π-π stacking of organic dye to enhance V_oc by decreasing charge recombination, and a hole-conducting function, evidenced by EIS and transient absorption spectra for the formation of carbazole cation radical species, to enhance V_oc and J_sc. As a result, a DSSC with the HC-A had improved efficiency by a factor of 1.33, compared to a similar solar cell without the HC-A. The photovoltaic performance of this DSSC exhibited a remarkably high J_sc of 17.25 mA/cm², a V_oc of 688 mV, a FF of 74.93% and a conversion efficiency of 8.89 % at 100 mW/cm². This is the best result reported for a DSSC employing the organic dye NKX2677. The detailed kinetics for a cascade-type hole-hopping process proposed here is complicated and constitutes another topic for research.

Chemistry – A European Journal published new progress about 373389-97-0. 373389-97-0 belongs to nitriles-buliding-blocks, auxiliary class OLED Materials,Red Fluorescence Dopants, name is 4-(3,6-Dibromo-9H-carbazol-9-yl)benzonitrile, and the molecular formula is C7H6O3, Related Products of nitriles-buliding-blocks.

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

Castro, E. A. published the artcileStructure and reactivity of arylcyanohydrins, Related Products of nitriles-buliding-blocks, the publication is Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie (1974), 29(3-4), 209-12, database is CAplus.

The relation between structure and reactivity was examined for 18 RCH(OH)CN (I, R = substituted phenyl) by CNDO/2 calculation of the stability of I (dissociation constant for I �RCHO + HCN) and of at. energy terms.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie 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, Related Products of nitriles-buliding-blocks.

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

Ronco, Cyril published the artcileSynthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors, Formula: C10H11N3O3S, the publication is Bioorganic & Medicinal Chemistry (2009), 17(13), 4523-4536, database is CAplus and MEDLINE.

A new series of huprines (12-amino-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolines, prepared as huperzine-tacrine hybrids) are prepared and their inhibition of recombinant human acetylcholinesterase (rh-AChE) is reported. We have synthesized two series of huprine analogs; in the first one, the benzene ring of the quinoline moiety has been replaced either by different heterocycles or by Ph groups with electron-withdrawing or electron-donating substituents. In the second series, different short linkers are introduced at the 12-positions of the huprine X and Y skeletons to evaluate the influence of modifications at the 12-position. The compounds are prepared from ethyl- or methyl-substituted bicyclo[3.3.1]non-6-en-3-one by Friedlaender reactions with o-aminocyano aromatic compounds The synthesis of two heterodimers with structures based on huprines has been also reported. Activities ranging from moderate to similar to those of huprines X and Y are obtained, with the most potent analog having a third of the activity of the parent huprines X and Y. Topol. data have been inferred from mol. docking; variation in activity with variation in the linking moieties suggest future structural modifications for activity improvement.

Bioorganic & Medicinal Chemistry 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, Formula: C10H11N3O3S.

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

Mailig, Melrose published the artcilePractical catalytic method for synthesis of sterically hindered anilines, Quality Control of 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(55), 11048-11051, database is CAplus and MEDLINE.

A practical catalytic method for the synthesis of sterically hindered anilines is described. The amination of aryl and heteroaryl boronic esters is accomplished using a catalyst prepared in situ from com. available and air-stable copper(I) triflate and a diphosphine ligand. For the first time, the method can be applied to the synthesis of both secondary and tertiary anilines in the presence of a wide range of functional groups. Esters, aldehydes, alcs., aryl halides, ketones, nitriles and nitro arenes are all compatible with the reaction conditions. Finally, even the most sterically hindered anilines can be successfully prepared under mild reaction conditions. Overall, the new method addresses significant practical limitations of a transformation previously developed and provides a valuable complement to the existing methods for the synthesis of anilines. Under optimized conditions the synthesis of the target compounds was achieved using 1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine] (i.e. phosphine-ether) and copper(I) triflate compound with benzene (2:1) as ligand-catalyst combination. Starting materials included N-(benzoyloxy)-N-(1-methylethyl)-2-propanamine (hydroxylamine derivative), benzoic acid 1-pyrrolidinyl ester, 4-(benzoyloxy)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester, benzoic acid 4-morpholinyl ester, benzoic acid 4-hydroxy-1-piperidinyl ester, benzoic acid 2,2,6,6-tetramethyl-1-piperidinyl ester. Boronic acid cyclic esters included 5,5-dimethyl-2-(2-methylphenyl)-1,3,2-dioxaborinane, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoic acid ester, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 2-chloro-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine, 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyrimidine, 5,5-dimethyl-2-(3-thienyl)-1,3,2-dioxaborinane (thiophene derivative). The title compounds thus formed included 4-bromo-N,N-bis(1-methylethyl)benzenamine (tertiary amine, tertiary aniline), 2,6-dimethyl-N-(1-methylethyl)benzenamine (secondary amine, secondary aniline). The reaction of a [1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine-.kappa .P]]copper complex intermediate with N-(benzoyloxy)-2-methyl-2-propanamine was reported.

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, Quality Control of 214360-44-8.

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

Franzen, H. published the artcileAction of cyanides on aldehydes and ketones, HPLC of Formula: 13312-84-0, the publication is Journal fuer Praktische Chemie (Leipzig) (1914), 293-306, database is CAplus.

cf. C. A., 7, 775. The crystalline metallic derivatives previously obtained by shaking cyanides of the alk. earths in H₂O with AcCH₂CO₂Et, BzCH₂CO₂Et, and Ac₂CH₂ are not metallic derivatives of cyanohydrins as then supposed, but metallic salts of the diketones and ketonic esters. The Ca, Sr, Ba and Mg salts of AcCH₂CO₂Et were prepared and the constitution of the Ca salt of mandelonitrile, Ca[OCH(CN)Ph]₂, was proven by its conversion into the Bz derivative, by shaking the Ca salt in Et₂O with BzCl. o-Calcium chloromandelonitrile was obtained in 62% yield from CaO, HCN and o-ClC₆H₄CHO, light yellow powder. The calcium, strontium and magnesium salts of Ac₂CH₂ were obtained in the form of needles from alc. From P-MeC₆H₄CHO was obtained, in 63% yield, calcium p-methylmandelonsirile in the form of orange-yellow crystals, which gave an intense blue coloration with concentrate H₂SO₄. p-Calcium methoxymandelonitrile was prepared from anisaldehyde. The labile, crystalline compound obtained by Kohn (Monalsh., 20, 903) by the action of HCHO on Ca(CN)₂, is shown to have the constitution Ca[OCH(CaOH)CN]₂.AcH forms a similar compound, crystallization powder. KCN and AcH yielded alanine and α-iminodipropionic acid.

Journal fuer Praktische Chemie (Leipzig) 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, HPLC of Formula: 13312-84-0.

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