Nitriles-buliding-blocks

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

Coumarins: Fast Synthesis by Knoevenagel Condensation under Microwave Irradiation was written by Bogdal, Dariusz. And the article was included in Journal of Chemical Research, Synopses in 1998.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

Condensation of salicylaldehyde or its derivatives with various derivatives of Et acetate in the presence of piperidine led to the synthesis of coumarins by a solvent free reaction under microwave irradiation For example, microwave irradiation of salicylaldehyde with di-Et malonate in the presence of piperidine gave 89% 3-ethoxycarbonylcoumarin. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mechanistic and Performance Studies on the Ligand-Promoted Ullmann Amination Reaction was written by Lo, Quintin A.;Sale, David;Braddock, D. Christopher;Davies, Robert P.. And the article was included in ACS Catalysis in 2018.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Over the last two decades many different auxiliary ligand systems have been utilized in the copper-catalyzed Ullmann amination reaction. However, there has been little consensus on the relative merits of the varied ligands and the exact role they might play in the catalytic process. Accordingly, in this work some of the most commonly employed auxiliary ligands have been evaluated for C-N coupling using reaction progress kinetic anal. (RPKA) methodol. The results reveal not only the relative kinetic competencies of the different auxiliary ligands but also their markedly different influences on catalyst degradation rates. For the model Ullmann reaction between piperidine and iodobenzene using the soluble organic base bis(tetra-n-butylphosphonium) malonate (TBPM) at room temperature, N-methylglycine was shown to give the best performance in terms of high catalytic rate of reaction and comparatively low catalyst deactivation rates. Further exptl. and rate data indicate a common catalytic cycle for all auxiliary ligands studied, although addnl. off-cycle processes are observed for some of the ligands (notably phenanthroline). The ability of the auxiliary ligand, base (malonate dianion), and substrate (amine) to all act competitively as ligands for the copper center is also demonstrated. On the basis of these results an improved protocol for room-temperature copper-catalyzed C-N couplings is presented with 27 different examples reported. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 4-(Benzylamino)benzonitrile

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

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

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

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

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

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