Tag: 100-200

A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents was written by Shaabani, Ahmad;Hooshmand, Seyyed Emad;Afaridoun, Hadi. And the article was included in Monatshefte fuer Chemie in 2017.SDS of cas: 70291-62-2 This article mentions the following:

The synergic effect of choline chloride/urea as a deep eutectic solvent was investigated in the synthesis of 2-aminothiophene derivatives via a three-component cyclocondensation of a ketone or an aldehyde with activated nitriles and elemental sulfur catalyzed by NaOH as cheap and highly accessible base. The advantages of this catalytic protocol were eco-friendly, easy to set up, reusability and a simple separation and purification of products without using chromatog. in high yields at short times. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2SDS of cas: 70291-62-2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pd/Cu-Catalyzed Domino Cyclization/Deborylation of Alkene-Tethered Carbamoyl Chloride and 1,1-Diborylmethane was written by Zhang, Chenhuan;Wu, Xianqing;Wang, Chenchen;Zhang, Chengxi;Qu, Jingping;Chen, Yifeng. And the article was included in Organic Letters in 2020.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Reported herein is a Pd/Cu cooperative-catalyzed dicarbofunctionalization of alkene-tethered carbamoyl chlorides with 1,1-diborylmethane. This cyclization/deborylation cascade strategy allows for the expedient formation of the versatile borylated 3,3-disubstituted oxindole skeleton, allowing for further functionalization via the derivatization of the C-B bond. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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. Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions was written by Itou, Tatsuya;Yoshimi, Yasuharu;Morita, Toshio;Tokunaga, Yuji;Hatanaka, Minoru. And the article was included in Tetrahedron in 2009.Category: nitriles-buliding-blocks This article mentions the following:

The photoreaction of dicyanobenzenes with aliphatic carboxylate ions afforded alkylcyanobenzenes and alkyldicyanobenzenes via decarboxylative substitution. The redox-photosensitized reaction system was effective in improving the product yield. The efficiency of this photoreaction depended on the structure of the carboxylate ion, and the product distribution varied with the dicyanobenzenes employed. This photoreaction was proved to be a clean process for the preparation of alkylcyanobenzenes. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Category: nitriles-buliding-blocks).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115閳?25 ppm whereas in isonitriles the shifts are around 155閳?65 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Substituent effects in free-radical reactions. A study of 4-substituted 3-cyanobenzyl free radicals was written by Fisher, T. H.;Meierhoefer, A. W.. And the article was included in Journal of Organic Chemistry in 1978.SDS of cas: 64113-86-6 This article mentions the following:

An extended Hammett treatment of the kinetics of N-bromosuccinimide bromination of I (R = H, halo, Me, Ph, MeO, NO₂, PhN:N, CN, MeCO) led to a free radical substituent constant (锜介垾?. The substituent order of free-radical stabilization was F < MeO < Me < H < Cl < Ph < I < Br < NO₂ < PhN:N < CN < MeCO. F and MeO destabilized the radical. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6SDS of cas: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Trace determination and occurrence of eight chlorophenylacetonitriles: An emerging class of aromatic nitrogenous disinfection byproducts in drinking water was written by Zhang, Di;Bond, Tom;Krasner, Stuart W.;Chu, Wenhai;Pan, Yang;Xu, Bin;Yin, Daqiang. And the article was included in Chemosphere in 2019.Product Details of 3218-45-9 This article mentions the following:

Two chlorophenylacetonitriles (CPANs) (2-chloro- and 3,4-dichlorophenylacetonitrile), representatives of an emerging class of aromatic nitrogenous disinfection byproducts, were recently identified in chlor(am)inated drinking water with liquid/liquid extraction and gas chromatog./mass spectrometry (GC/MS). Due to their high cytotoxicity, they are potentially significant drinking water contaminants. The detection limit for these two CPANs with the previous method was 100 ng L^-1. To search for addnl. CPAN isomers, a more sensitive method for the simultaneous determination of eight CPANs was developed using solid-phase extraction (SPE)-GC/MS. GC/MS parameters and SPE pre-concentration conditions, including SPE cartridge, eluent type, eluent volume, and sample pH, were optimized. Under optimized conditions, the new method had method detection limits, method quantification limits, and precision ranging from 0.15 to 0.37 ng L^-1, 0.50-0.95 ng L^-1, and 5.8%-11%, resp. The recoveries of the eight CPANs ranged from 92% to 102%. The concentrations of the eight CPANs in nine finished drinking waters were determined to be at concentrations ranging from 0.5 to 155 ng L^-1. Seven CPANs were detectable in all samples. CPANs were detected at concentrations between 0.8 and 155 ng L^-1 in chlorinated waters, and from 0.5 to 15 ng L^-1 in chloraminated waters. Across all waters, the sum of all CPANs in chloraminated waters was 13% of that in chlorinated systems. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9Product Details of 3218-45-9).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Product Details of 3218-45-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Influence of the branching of the dienophile on the Diels-Alder reaction with butadiene and its derivatives. I. Nitriles and methyl esters of acrylic and methacrylic acids was written by Doucet, Jeannine;Rumpf, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1954.Name: 4-Hydroxycyclohexanecarbonitrile This article mentions the following:

The Me group of methacrylic derivatives does not prevent the diene condensation but lowers yields and requires elevation of reaction T. The order of the following data are diene, dienophile, time in hrs., T鎺矯., product, b.p.鎺矯., n¹⁶_D, % yield: (1) butadiene, Me acrylate, 5, 160, Me ester of 1-carboxy-3-cyclohexene, b₁₅ 72, 1.4635, 95; (2) butadiene, Me methacrylate, 8.5, 220, Me ester of 1-methyl-1-carboxycyclohex-3-ene, b₁₆ 73-5, 1.462, 65; (3) butadiene, acrylonitrile, 12,135, 1-cyano-3-cyclohexene, b₂₀ 83, 1.477, 83; (4) butadiene, methacrylonitrile, 13,180, 1-methyl-1-cyanocyclohex-3-ene, b₂₀ 83, 1.472, 53; (5) 2-ethoxybutadiene, Me acrylate, 5,160, Me ester of 1-carboxy-4-ethoxycyclohex-3-ene, b₁₅ 125-6, 1.464, 50; (6) 2-ethoxybutadiene, acrylonitrile, 12, 135-40, 1-cyano-4-ethoxycyclohex-3-ene, b₁₅ 125-6, n²⁰_D 1.4775, 90; (7) 2-ethoxybutadiene, methacrylonitrile, 12,180, 1-methyl-1-cyano-4-ethoxy-3-cyclohexene, b₁₅ 125-6, 1.478, 50; (8) chloroprene, Me acrylate, 5,160, Me ester of 1-carboxy-4-chlorocyclohex-3-ene, b₁₅ 109-11, 1.485, 60; (9) chloroprene, Me methacrylate, 9, 185-90, Me ester of 1-methyl-1-carboxy-4-chlorocyclo-3-hexene, b₂₃ 119-21, 1.491, 38; (10) chloroprene, acrylonitrile, 12,135, 1-cyano-4-chlorocyclohex-3-ene, b₂₀ 127-30, m. 54, no index of refraction, 34; (11) chloroprene, methacrylonitrile, 12,180, 1-methyl-1-cyano-4-chlorocyclohex-3-ene, b₁₅ 114-16, 1.511, 11. In connection with these studies the following compounds were reported: (a) acid chloride (b₁₄ 88鎺? and anhydride (b₁₄ 188-9鎺? of 1,2,5,6-tetrahydrobenzoic acid; (b) 1-methyl-1,2,5,6-tetrahydrobenzoic acid (m. 77鎺?, its acid chloride (b₁₅ 74-6鎺?, its amide (m. 87鎺?, its anhydride (b₁₈ 182鎺?; (c) 1-propionyl-1-methyl-3-cyclohexene (b₂₀ 96-7鎺? n 1.478), its 2,4-dinitrophenylhydrazone (m. 74.5鎺?, its hydrazone (b₂₀ 165鎺?, a condensation product of 2 mol of 1-propionyl-1-methyl-3-cyclohexene (b₂₀ 150鎺?; (d) 1-propionyl-1-methyl-3-cyclohexanol (b₁₉ 1 3-5鎺? and its p-nitrobenzoate (m. 194鎺?; (e) from 1,2,5,6-tetrahydrobenzonitrile and MeMgI (or EtMgBr) were formed ketones (b₁₈ 76鎺?and b₁₆ 84.5鎺? resp.), their semicarbazones m. 173.5鎺?and 147鎺?and their 2,4-dinitrophenylhydrazones m. 144鎺?and 141鎺? (f) 1-cyanocyclohexan-4-one (b₁₂ 139-41鎺? was made from 1-cyano-4-ethoxy-3-cyclohexene; (g) 1-cyanocyclohexan-4-ol (b₁₂ 153-4鎺? was made by reduction of 1-cyanocyclohexan-4-one. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Name: 4-Hydroxycyclohexanecarbonitrile).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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. 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.Name: 4-Hydroxycyclohexanecarbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Enantioselective Construction of Trifluoromethoxylated Stereogenic Centers by a Nickel-Catalyzed Asymmetric Suzuki-Miyaura Coupling of Secondary Benzyl Bromides was written by Huang, Weichen;Wan, Xiaolong;Shen, Qilong. And the article was included in Angewandte Chemie, International Edition in 2017.Related Products of 36057-44-0 This article mentions the following:

Trifluoromethoxy-substituted stereogenic centers I [R = 4-C(O)OCH₃, C(O)CH₃, NO₂, CN, 3,5-(Br)₂; Ar = C₆H₅, C₆H₄CH=CH₂, [3-(morpholin-4-yl)phenyl], naphthalen-2-yl, etc.] can be constructed with high enantioselectivity by a nickel-catalyzed Suzuki-Miyaura coupling of readily available 浼?bromobenzyl trifluoromethyl ethers RC₆H₄(OCF₃)Br with a variety of aryl pinacol boronates II. The coupling proceeds under mild reaction conditions, and a variety of common functional groups, such as fluoride, chloride, bromide, ester, enolizable ketone, nitro, cyano, amino, and vinyl moieties, were well tolerated. Furthermore, the reaction can be easily scaled up to gram quantities without a decrease in enantioselectivity. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Related Products of 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.Related Products of 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Light-mediated cyanomethylation of cycloalkenes with acetonitrile was written by Sonawane, Harikisan R.;Bellur, Nanjundiah S.;Shah, Virendra G.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1990.SDS of cas: 4435-14-7 This article mentions the following:

The addition of cyanomethyl radicals, generated from MeCN via photoinduced decomposition of H₂O₂, to cycloalkenes gave cycloalkylmethyl nitriles and cycloalkanols. The homolytic cyanomethylation of 3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane gave endo-2-(2-cyanoethyl)- and endo-2-(hydroxymethyl)-3,3-dimethylbicyclo[2.2.1]heptane in 76% overall yield in a 49:51 product ratio. The homolytic cyanomethylation of norbornene gave exo-2-(cyanomethyl)bicyclo[2.2.1]heptane and exo-norborneol in 72% overall yield in a 80:20 product ratio. The reaction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C閳ユ弲 bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct cyanomethylation of aliphatic and aromatic hydrocarbons with acetonitrile over a metal loaded titanium oxide photocatalyst was written by Wada, Emiko;Takeuchi, Tomoaki;Fujimura, Yuki;Tyagi, Akanksha;Kato, Tatsuhisa;Yoshida, Hisao. And the article was included in Catalysis Science & Technology in 2017.Recommanded Product: 4435-14-7 This article mentions the following:

A platinum-loaded TiO₂ (Pt/TiO₂) photocatalyst promoted cyanomethylation of aliphatic hydrocarbons, namely cyclohexane and cyclohexene, with acetonitrile, where the photogenerated hole oxidatively dissociates the C-H bond of both the acetonitrile and the aliphatic hydrocarbons to form each corresponding radical species before their radical cross-coupling. The Pt/TiO₂ photocatalyst was more active than the Pd/TiO₂ photocatalyst in these reactions. In contrast, the cyanomethylation of benzene was promoted by the Pd/TiO₂ photocatalyst or a phys. mixture of the Pt/TiO₂ photocatalyst and a Pd catalyst supported by Al₂O₃, while it was hardly promoted by the Pt/TiO₂ photocatalyst alone. The temperature dependence of the reaction rate proved that the Pd nanoparticles on the TiO₂ thermally function as a metal catalyst. However, in the cyanomethylation of aliphatic hydrocarbons, the catalytic effect of the metal particles was not observed, meaning that the radical coupling takes place without the metal catalysis. Thus, it is concluded that in the case of the benzene cyanomethylation the Pd nanoparticles play dual roles, as a catalyst to catalyze the substitution reaction of benzene with the cyanomethyl radical, and as an electron receiver to reduce the recombination of the photoexcited electrons and holes in the TiO₂ photocatalyst, although they could not contribute as a catalyst to the cyanomethylation of aliphatic hydrocarbons. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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. Recommanded Product: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts