Tag: 100-200

Ligand-Promoted Non-Directed C-H Cyanation of Arenes was written by Liu, Luo-Yan;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Chemistry – A European Journal in 2019.Quality Control of 3-(tert-Butyl)benzonitrile This article mentions the following:

The first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent was reported. This protocol was compatible with a broad scope of arenes, including advanced intermediates, drug mols. and natural products. A kinetic isotope experiment (k_H/k_D=4.40) indicated that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Quality Control of 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 3-(tert-Butyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Silver co-ordination compounds with aliphatic nitriles containing amino nitrogen as H bond donor or additional metal binding site: formation of a ring, a chain, a polymeric sheet and a 3D polymeric channeled structure was written by Erxleben, Andrea. And the article was included in CrystEngComm in 2002.HPLC of Formula: 7528-78-1 This article mentions the following:

Three coordination polymers and a discrete 20-membered macrometallacycle were prepared by crystallization of Ag salts with the conformationally flexible, polyfunctional ligands N-(2-cyanoethyl)glycine (ceg), 3,3-iminodipropionitrile (idpn) and tris(2-cyanoethyl)amine (tca). Single-crystal x-ray analyses of [Ag₂(tca)₂](ClO₄)₂ (1), [Ag(idpn)]ClO₄ (2), [Ag(ceg)]CF₃SO₃ (3) and [Ag(ceg)]ClO₄·0.5H₂O (4) revealed a bimetallic macrocycle (1), a 2-dimensional sheet structure with 4.8² topol. (2), a 3-dimensional network structure with rhomboid channels (3) and a 1-dimensional chain structure (4). The rhomboid channels in 3 are generated by 36-membered macrometallacyclic subunits consisting of four Ag atoms and four ceg ligands with ceg binding through the carboxylate group and the nitrile N. The amino N of ceg is protonated and serves as a H bond donor for the triflate anions that are incorporated into the macrocycles, thus stabilizing the channeled structure. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1HPLC of Formula: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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).HPLC of Formula: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New heterocyclic Meisenheimer complexes. Action of methoxide and hydride ions on 2,4-substituted thiophenes and selenophenes was written by Paulmier, Claude;Simonnin, Marie Paule;Chatrousse, Alain Pierre;Terrier, Francois. And the article was included in Tetrahedron Letters in 1973.Electric Literature of C5H2N2O2S This article mentions the following:

Meisenheimer complexes, formed by addition of MeOK to 2,4-disubstituted thiophenes and selenophenes (I; X = S, Se; R, R1 = NO2, CN), were assigned structure II (R2 = OMe) from NMR data. Addition of Me4NBH4 to I (X = S; R = NO2, CN, R1 = NO2) gave analogous II (R = NO2, CN; R1 = NO2; R2 = H), but with I (X = S, R = NO2, R1 = CN; X = Se, R, R1 = NO2, CN) ring-opening occurred. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Electric Literature of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity was written by Du, Tian;Wang, Biwen;Wang, Chao;Xiao, Jianliang;Tang, Weijun. And the article was included in Chinese Chemical Letters in 2021.Related Products of 101219-69-6 This article mentions the following:

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asym. hydrogenation of a wide range of aryl ketones, affording chiral alcs. with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand showed a remarkable effect on the enantioselectivity of the reaction. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. 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.Related Products of 101219-69-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new synthesis of benzo[b]thiophenes and benzo[c]thiophenes by annulation of disubstituted thiophenes was written by Terpstra, Jan W.;Van Leusen, Albert M.. And the article was included in Journal of Organic Chemistry in 1986.Computed Properties of C6H5NS This article mentions the following:

Nine newly prepared ortho-disubstituted thiophenes I (R = CHO, CO₂Me, cyano; n = 1, 2) and II (R = CO₂Me, cyano, n = 1, 2) react with Michael acceptors to form benzo[b]-, e.g. III, and benzo[c]thiophenes, e.g. IV. This novel annulation process is specifically suited to form benzothiophenes with substituents in the benzene moiety. Substitution patterns so obtained are uncommon and difficultly accessible otherwise; none of the 31 benzothiophenes described in this paper were reported previously. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Site-selectivity in the cyanation of 3-substituted pyridine 1-oxides with trimethylsilanecarbonitrile was written by Sakamoto, Takao;Kaneda, Sohichi;Nishimura, Sumiko;Yamanaka, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Quality Control of 4-methoxypicolinonitrile This article mentions the following:

Treatment of pyridine 1-oxides I (R = Br, Cl, F, OMe, NMe₂, Me, Et, Ph, CONEt₂, CO₂Et, cyano) with Me₃SiCN gave 2- and 6-cyanopyridines II and III. The II – III ratio was strongly influenced by R, with II being the only product when R = F, OMe, NMe₂. Nitropyridine 1-oxides underwent deoxygenation but not cyanation with Me₃SiCN. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Quality Control of 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Quality Control of 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent was written by Dohi, Toshifumi;Ito, Motoki;Yamaoka, Nobutaka;Morimoto, Koji;Fujioka, Hiromichi;Kita, Yasuyuki. And the article was included in Tetrahedron in 2009.Formula: C6H5NS This article mentions the following:

Bithiophenes and bipyrroles are prepared regioselectively by oxidative coupling reactions of thiophenes and pyrroles mediated by hypervalent iodine reagents such as PhI(O₂CCF₃)₂ (PIFA) in the presence of Lewis acids. Substituted thiophenes and thiophenecarbonitriles, pyrrolecarbonitriles, and indolecarbonitriles are prepared by oxidative substitution reactions of thiophenes, N-tosylpyrroles, and N-tosylindoles with PIFA in the presence of boron trifluoride etherate and nucleophiles such as trimethylsilyl cyanide. (thienyl)aryliodonium salts are prepared by reaction of 3-methylthiophene with either PIFA or with iodosobenzene and acids or by reactions of (hydroxy)aryliodonium tosylates with thiophenes in 2,2,2-trifluoroethanol. All of the above reactions are proposed to occur via single-electron oxidation of the substrates with hypervalent iodine reagents. The paper is preceded by a review of the work of the Kita research group on oxidative cyclizations and intramol. oxidative coupling reactions of arenes mediated by hypervalent iodine reagents. 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. 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.Formula: C6H5NS

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes was written by Kaki, Venkata Rao;Akkinepalli, Raghuram Rao;Deb, Pran Kishore;Pichika, Mallikarjuna Rao. And the article was included in Synthetic Communications in 2015.Application In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

A simple, efficient, and environmentally friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The electronic effect of the CN group in the aromatic and thiophene series was written by Tirouflet, J.. And the article was included in Bulletin de la Societe Chimique de France in 1958.Formula: C5H2N2O2S This article mentions the following:

A Hammet σ constant was determined for the CN group of nitrothiophenenitriles by polarographic reduction. Thiophene and POCl₃ in HCONMe₂ gave 2-thiophenecarboxaldehyde (I), which with HNO₃ gave 4-nitro-2-thiophenecarboxaldehyde, and with HNO₃ in Ac₂O gave the 5-NO₂ isomer. Oximation of the aldehyde followed by dehydration gave 2-cyano-4-nitro-thiophene (II) and the 5-NO₂ isomer (III), resp. The half-wave potentials of these compounds, determined at pH 3.10, permitted calculation of σ for the CN group of II and III as 0.69 and 1.0, resp., compared with 0.69 and 0.94 for Ac of the corresponding 2-Ac derivatives The difference in half-wave potentials was sufficient (0.14 v.) to allow quant. determination of II and III, particularly by oscillopolarography (the polarograms are illustrated). The product of nitration of 2-cyanothiophene was thus found to contain 42% II and 58% III. Nitration of 2-acetylthiophene and I gave 52% and 75%, resp., of the 4-NO₂ derivative A review of previous determinations of σ for the aromatic CN group is also included. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Formula: C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

General preparation of 3-aryl-3,4-dimethylpentan-4-olides by intramolecular rearrangement was written by Tsatsas, Georges;Cotakis, G.. And the article was included in Bulletin de la Societe Chimique de France in 1970.Related Products of 5351-07-5 This article mentions the following:

Treatment of 3,4-RR1C6H3C(Bu-tert)(OH)CH2CO2R2 (I, R = H, MeO; R1 = H, Cl, MeO, Me, Br; R2 = H, Et) with AcCl and Ac2 3,4-RR1C6H3C(Bu-tert):CH2 and II were also isolated from the above reaction with I (R2 = H). II were also prepared from I by reaction with concentrated H2SO4. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Related Products of 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.Related Products of 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts