Category: 55406-13-8

Redox-Active Reagents for Photocatalytic Generation of the OCF₃ Radical and (Hetero)Aryl C-H Trifluoromethoxylation was written by Zheng, Weijia;Lee, Johnny W.;Morales-Rivera, Cristian A.;Liu, Peng;Ngai, Ming-Yu. And the article was included in Angewandte Chemie, International Edition in 2018.HPLC of Formula: 55406-13-8 This article mentions the following:

The trifluoromethoxy (OCF₃) radical is of great importance in organic chem. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF₃ radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermol. C-H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds Exptl. and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF₃ radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8HPLC of Formula: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cyanation of Aryl Bromides with K₄[Fe(CN)₆] Catalyzed by Dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium, a Molecular Source of Nanoparticles, and the Reactions Involved in the Catalyst-Deactivation Processes was written by Gerber, Roman;Oberholzer, Miriam;Frech, Christian M.. And the article was included in Chemistry – A European Journal in 2012.Synthetic Route of C6H5NS This article mentions the following:

Dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium [(P{(NC₅H₁₀)(C₆H₁₁)₂})₂PdCl₂] (1) is a highly active and generally applicable C-C cross-coupling catalyst. Apart from its high catalytic activity in Suzuki, Heck, and Negishi reactions, compound 1 also efficiently converted various electronically activated, nonactivated, and deactivated aryl bromides, which may contain fluoride atoms, trifluoromethane groups, nitriles, acetals, ketones, aldehydes, ethers, esters, amides, as well as heterocyclic aryl bromides, such as pyridines and their derivatives, or thiophenes into their resp. aromatic nitriles with K₄[Fe(CN)₆] as a cyanating agent within 24 h in NMP at 140 鎺矯 in the presence of only 0.05 mol % catalyst. Catalyst deactivation processes showed that excess cyanide efficiently affected the mol. mechanisms as well as inhibited the catalysis when nanoparticles were involved, owing to the formation of inactive cyanide complexes, such as [Pd(CN)₄]^2-, [(CN)₃Pd(H)]^2-, and [(CN)₃Pd(Ar)]^2-. Thus, the choice of cyanating agent is crucial for the success of the reaction because there is a sharp balance between the rate of cyanide production, efficient product formation, and catalyst poisoning. For example, whereas no product formation was obtained when cyanation reactions were examined with Zn(CN)₂ as the cyanating agent, aromatic nitriles were smoothly formed when hexacyanoferrate(II) was used instead. The reason for this striking difference in reactivity was due to the higher stability of hexacyanoferrate(II), which led to a lower rate of cyanide production, and hence, prevented catalyst deactivation processes. This pathway was confirmed by the colorimetric detection of cyanides: whereas the conversion of 灏?solvato-浼?cyanocobyrinic acid heptamethyl ester into dicyanocobyrinic acid heptamethyl ester indicated that the cyanide production of Zn(CN)₂ proceeded at 25 鎺矯 in NMP, reaction temperatures of >100 鎺矯 were required for cyanide production with K₄[Fe(CN)₆]. Mechanistic investigations demonstrate that palladium nanoparticles were the catalytically active form of compound 1. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Synthetic Route of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Synthetic Route of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades was written by Zheng, Haoteng;Xiao, Qinjie;Mao, Feiying;Wang, Anming;Li, Mu;Wang, Qiuyan;Zhang, Pengfei;Pei, Xiaolin. And the article was included in RSC Advances in 2022.Synthetic Route of C6H5NS This article mentions the following:

In this work, a greener chemo-enzymic cascade to synthesize alky and aryl nitriles RCN (R = Ph, Bn, pentyl, furan-2-yl, etc.) from readily accessible aldehydes RCHO, that were further transformed into corresponding amides RC(O)NH₂ via an artificial enzyme cascade was reported. A biphasic reaction system was designed to bridge chem. synthesis and enzymic catalysis through simple phase separation The biphasic system mainly perfectly avoided the inactivation of hydroxylamine on aldoxime dehydratase from Pseudomonas putida (OxdF1) and nitrile hydratase from Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229). For the synthesis of various nitriles, moderate isolation yields of approx. 60% were obtained by the chemo-enzymic cascade. Interestingly, two seemingly conflicting reactions of dehydration and hydration were sequentially proceeded to synthesize amides by the synergistic catalysis of OxdF1 and NHase1229 in E. coli cells. An isolation yield of approx. 62% was achieved for benzamide at the one-liter scale. In addition, the shuttle transport of substrates and products between two phases is convenient for the product separation and n-hexane recycling. Thus, the chemo-enzymic cascade shows a potential application in the cyanide-free and large-scale synthesis of nitriles and amides. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Synthetic Route of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two 锜? bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Synthetic Route of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades was written by Zheng, Haoteng;Xiao, Qinjie;Mao, Feiying;Wang, Anming;Li, Mu;Wang, Qiuyan;Zhang, Pengfei;Pei, Xiaolin. And the article was included in RSC Advances in 2022.Synthetic Route of C6H5NS This article mentions the following:

In this work, a greener chemo-enzymic cascade to synthesize alky and aryl nitriles RCN (R = Ph, Bn, pentyl, furan-2-yl, etc.) from readily accessible aldehydes RCHO, that were further transformed into corresponding amides RC(O)NH₂ via an artificial enzyme cascade was reported. A biphasic reaction system was designed to bridge chem. synthesis and enzymic catalysis through simple phase separation The biphasic system mainly perfectly avoided the inactivation of hydroxylamine on aldoxime dehydratase from Pseudomonas putida (OxdF1) and nitrile hydratase from Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229). For the synthesis of various nitriles, moderate isolation yields of approx. 60% were obtained by the chemo-enzymic cascade. Interestingly, two seemingly conflicting reactions of dehydration and hydration were sequentially proceeded to synthesize amides by the synergistic catalysis of OxdF1 and NHase1229 in E. coli cells. An isolation yield of approx. 62% was achieved for benzamide at the one-liter scale. In addition, the shuttle transport of substrates and products between two phases is convenient for the product separation and n-hexane recycling. Thus, the chemo-enzymic cascade shows a potential application in the cyanide-free and large-scale synthesis of nitriles and amides. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Synthetic Route of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Synthetic Route of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cyano-substituted 5-thiabicyclo[2.1.0]pent-2-enes: reactions and relevance to cyanothiophene phototranspositions was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.Quality Control of 3-Methylthiophene-2-carbonitrile This article mentions the following:

The title thiabicyclopentenes were detected by NMR as intermediates in the photorearrangements of cyanothiophenes. Thiabicyclopentene I was obtained (6%) on irradiation of 3-cyano-2-methyl- or -4-methylthiophene in cyclohexane at ∼34°. Aromatization and rearrangement by S walk of I, which occur photochem. and thermally, and its Diels-Alder reactions with furan and 2,5-diphenyl-3,4-benzofuran were studied. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Quality Control of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Quality Control of 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development of potential manufacturing routes for substituted thiophenes – preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides was written by Hull, John W. Jr.;Romer, Duane R.;Podhorez, David E.;Ash, Mezzie L.;Brady, Christine H.. And the article was included in Beilstein Journal of Organic Chemistry in 2007.Recommanded Product: 55406-13-8 This article mentions the following:

Potential manufacturing routes to three halogenated 2-thiophenecarboxylic acid derivatives, namely, 4-bromo-3-methyl-2-thiophenecarbonyl chloride, 3,4,5-trichloro-2-thiophenecarbonyl chloride, and 3,4,5-trichloro-2-thiophenecarbonitrile, from com. available thiophene raw materials have been developed and demonstrated on a laboratory scale. A one-pot bromination/debromination procedure developed for 3-methylthiophene gave 2,4-dibromo-3-methylthiophene. Carboxylic acid functionality was then introduced either by a Grignard metalation followed by carbonation with CO₂, or by a palladium catalyzed carbonylation procedure under CO pressure. The vapor phase chlorination of 2-thiophenecarbonitrile with chlorine gas at 500 °C with an average residence time of 6 s gave 3,4,5-trichloro-2-thiophenecarbonitrile in a 69% distilled yield, a process that was carried out on a multi-kilogram scale in the laboratory Finally, a route for the preparation of 3,4,5-trichloro-2-thiophenecarbonyl chloride was developed from tetrachlorothiophene via either a lithiation reaction with n-butyllithium in MTBE, or by a previously reported Grignard method using 1,2-dibromoethane as activator, followed by carbonation of the anion with CO₂ to give the trichloro-2-thiophenecarboxylic acid, which was readily converted to the corresponding acid chloride with SOCl₂. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Recommanded Product: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Recommanded Product: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thermochemistry of substituted thiophenecarbonitrile derivatives was written by Ribeiro da Silva, Manuel A. V.;Santos, Ana Filipa L. O. M.. And the article was included in Journal of Chemical Thermodynamics in 2008.Electric Literature of C6H5NS This article mentions the following:

The standard (p° = 0.1 MPa) molar energies of combustion in oxygen of 2-thiophenecarbonitrile, 3-thiophenecarbonitrile, 2-thiopheneacetonitrile, 3-thiopheneacetonitrile, and 3-methyl-2-thiophenecarbonitrile were measured, at T = 298.15 K, by rotating-bomb calorimetry. The standard molar enthalpies of vaporization of these compounds at T = 298.15 K were determined using high temperature Calvet microcalorimetry. These values were used to derive the standard molar enthalpies of formation of the title compounds in their crystalline and gaseous phases. The standard molar enthalpies of formation for the title compounds in the gaseous state were derived and the results are interpreted in terms of structural effects. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Electric Literature of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Electric Literature of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent was written by D’Aleo, Danielle N.;Allard, Sheena R.;Foglia, Cassandra C.;Parent, Shawna L. M.;Rohr, David J.;Gottardo, Christine;MacKinnon, Craig D.. And the article was included in Canadian Journal of Chemistry in 2013.Formula: C6H5NS This article mentions the following:

The green generation of X⁺ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quant. for positions to the sulfur; pyrroles also give quant. reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alc., nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochem. were very similar to reactions involving N-bromosuccinimide in THF solvent. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Formula: C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Formula: C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Novel and Direct Oxidative Cyanation Reactions of Heteroaromatic Compounds Mediated by A Hypervalent Iodine(III) Reagent was written by Dohi, Toshifumi;Morimoto, Koji;Kiyono, Yorito;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Organic Letters in 2005.Application In Synthesis of 3-Methylthiophene-2-carbonitrile This article mentions the following:

The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) mediates the selective cyanation reactions of a wide range of electron-rich heteroaromatic compounds such as pyrroles, thiophenes, and indoles under mild conditions. These reactions proceed via a cation radical intermediate, and the key for the successful transformation presumably depends on the oxidation-reduction potential of the substrates used. The synthetic utility has been demonstrated through the conversion of these biol. important pyrroles 2f and 2g. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Application In Synthesis of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development of Pd/C-Catalyzed Cyanation of Aryl Halides was written by Yu, Hannah;Richey, Rachel N.;Miller, William D.;Xu, Jiansheng;May, Scott A.. And the article was included in Journal of Organic Chemistry in 2011.Computed Properties of C6H5NS This article mentions the following:

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Computed Properties of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Computed Properties of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts