Month: February 2023

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

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

An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature was written by Chaudhary, Priyanka;Korde, Rishi;Gupta, Surabhi;Sureshbabu, Popuri;Sabiah, Shahulhameed;Kandasamy, Jeyakumar. And the article was included in Advanced Synthesis & Catalysis in 2018.Related Products of 10282-32-3 This article mentions the following:

A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester are very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the addnl. features of the current methodol. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. 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. Related Products of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and dyeing characteristics of ethyl 1-(2-acetamido-3-cyano-5-carbethoxythiophen-4-yl)glyoxalate(aryl)hydrazones was written by Sabnis, R. W.;Rangnekar, D. W.. And the article was included in Indian Journal of Fibre & Textile Research in 1992.Formula: C12H14N2O4S This article mentions the following:

Five monoazo disperse dyes, Et 1-(2-acetamido-3-cyano-5-carbethoxythiophen-4-yl)glyoxalate-(aryl)hydrazones, were prepared and their dyeing performance on polyester fibers was assessed. The dyeings on polyester had orange red and bright red shades with low pickup, moderate light fastness and good sublimation fastness. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Formula: C12H14N2O4S).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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. 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.Formula: C12H14N2O4S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp²)-H Arylation, Cyclization, and Migration Tandem Reaction was written by Gou, Bo-Bo;Yang, Hui;Sun, Huai-Ri;Chen, Jie;Wu, Junliang;Zhou, Ling. And the article was included in Organic Letters in 2019.Computed Properties of C11H13NO This article mentions the following:

Phenanthrene is an important structural motif in chem. and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsym. phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp²)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of sym. and unsym. phenanthrenes with diversified functional groups were synthesized with good to excellent yields. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Computed Properties of C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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 C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines was written by Malkov, Andrei V.;Stewart-Liddon, Angus J. P.;McGeoch, Grant D.;Ramirez-Lopez, Pedro;Kocovsky, Pavel. And the article was included in Organic & Biomolecular Chemistry in 2012.HPLC of Formula: 36057-44-0 This article mentions the following:

A new family of Lewis basic 2-pyridyloxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyloxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee). In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0HPLC of Formula: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.HPLC of Formula: 36057-44-0

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

Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds was written by Volmajer, Julija;Toplak, Renata;Leban, Ivan;Majcen Le Marechal, Alenka. And the article was included in Tetrahedron in 2005.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The Knoevenagel reaction between 2-hydroxybenzaldehydes and active methylene compounds (malononitrile and Et cyanoacetate) produced iminocoumarins, e.g., I, and/or coumarins. In order to study the reactivity of the prepared iminocoumarins, chlorination and reaction with N-nucleophiles were studied. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Enantioselective catalytic reduction of ketones using C₂-symmetric diamines as chiral ligands was written by Gamez, Patrick;Fache, Fabienne;Mangeney, Pierre;Lemaire, Marc. And the article was included in Tetrahedron Letters in 1993.Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

The catalytic enantioselective reduction of various prochiral ketones is reported using C₂-sym. diamines as ligands. Up to 99% e.e. at 100% conversion are obtained. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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 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.Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile

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