Tag: 200-300

Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion was written by Wang, Xu;Xiong, Wenfang;Huang, Yubing;Zhu, Jiayi;Hu, Qiong;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Organic Letters in 2017.Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols was written by Blank, Benoit;Madalska, Martyna;Kempe, Rhett. And the article was included in Advanced Synthesis & Catalysis in 2008.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

An efficient multi-gram scale synthesis protocol of a variety of P,N ligands is described. The synthesis is achieved in a two-step reaction. First, the amine is deprotonated and subsequently the chlorophosphine is added to yield the corresponding P,N ligand. Deprotonation of the amine is normally achieved with BuLi at low temperature, but for the preparation of ligands with a 2,2′-dipyridylamino backbone and phosphines with a high steric demand KH has to be employed in combination with reaction temperatures of 110鎺矯 for the salt metathesis step. The reaction of two equivalent of a selected P,N ligand with one equivalent of the iridium complex [IrCl(cod)]₂ (cod = 1,5-cyclooctadiene) affords P,N ligand-coordinated iridium complexes in quant. yield. X-Ray single crystal structure anal. of one of these complexes reveals a monomeric five-coordinated structure in the solid state. The iridium complexes were used to form catalysts for the N-alkylation of aromatic amines with alcs. The catalyst system was optimized by studying 8 different P,N ligands, 9 different solvents and 14 different bases. Systematic variation of the substrate to base and the amine to alc. ratios as well as the catalyst loading led to optimized catalytic reaction conditions. The substrate scope of the developed catalytic protocol was shown by synthesizing 20 different amines of which 12 could be obtained in isolated yields higher than 90%. A new efficient catalyst system for the selective monoalkylation of primary aromatic and heteroaromatic amines with primary aromatic, heteroaromatic as well as aliphatic alcs. has been established. The reaction proceeds with rather moderate catalyst loadings. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 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. 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.Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new, fast and easy strategy for one-pot synthesis of full substituted cyclopropanes: direct transformation of aldehydes to 3-aryl-1,1,2,2-tetracyanocyclopropanes was written by Pesyan, Nader Noroozi;Kimia, Mohammad Ali;Jalilzadeh, Mohammad;Sahin, Ertan. And the article was included in Journal of the Chinese Chemical Society (Weinheim, Germany) in 2013.Recommanded Product: 55490-87-4 This article mentions the following:

A new, fast and easy method for a one-pot reaction of aromatic aldehydes and dialdehydes with malononitrile and cyanogen bromide was developed to afford substituted 3-arylcyclopropane-1,1,2,2-tetracarbonitrile derivatives in excellent yield in a very short time (about 5 s). The product structures were characterized by IR, ¹H-NMR, ¹³C-NMR, mass spectrometry and X-ray crystallog. techniques. For these compounds the crystallog. data showed two structures in a mirror image in solid case and one distinct structure in solution A reaction mechanism was discussed, whereby the synthesis of the target compounds was achieved by the formation of triethylammonium bromodicyanomethanide (I) as a key intermediate. The title compounds thus formed included 3-(2-nitrophenyl)-1,1,2,2-cyclopropanetetracarbonitrile (II) and related substances, such as a naphthalene, pyridine, furan and anthracene derivative A reaction of 1,4-benzenedicarboxaldehyde provided a dimer-type compound [3,3′-(1,4-phenylene)bis[1,1,2,2-cyclopropanetetracarbonitrile]]. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solid-state fluorescence properties of small iminocoumarin derivatives and their analogues in the coumarin series was written by Abid-Jarraya, Nihel;Khemakhem, Kacem;Turki-Guermazi, Hamida;Abid, Souhir;Saffon, Nathalie;Fery-Forgues, Suzanne. And the article was included in Dyes and Pigments in 2016.Recommanded Product: 51473-74-6 This article mentions the following:

Considering the many potential applications of fluorescent materials, dyes that exhibit emission in the solid state are in high demand, especially if they are easy to prepare and inexpensive. In this respect, exploring the behavior of basic iminocoumarins seemed relevant. The spectroscopic properties of 3-cyano-7-diethylamino-2-iminocoumarin and a derivative bearing an ethoxycarbonyl group were therefore studied in the solid state, and a comparison was made with the corresponding coumarin. The three compounds had very close fluorescence properties in solution In contrast, the coumarin derivative was much more emissive in the solid state than the iminocoumarins. This discrepancy was tentatively related to the crystal packing modes. A comparison was made with 7-diethylaminocoumarin to clarify the role of the cyano group, which may not be advantageous from a spectroscopic viewpoint. Using a solvent-exchange method, the three cyano compounds generated elongated microparticles, the substituted iminocoumarin derivative even led to flat microfibers. This work shows that small coumarins are valuable solid-state fluorescent dyes while small iminocoumarins should be used as building blocks to access more elaborated compounds if solid-state applications are envisaged. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. 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.Recommanded Product: 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of strontium ranelate, an antiosteoporosis drug was written by Ding, Xiangyu;Jiang, Ye;Jia, Xiangman;Liu, Fenghua. And the article was included in Zhongguo Yaoxue Zazhi (Beijing, China) in 2008.SDS of cas: 58168-20-0 This article mentions the following:

The synthesis route of strontium ranelate, an antiosteoporosis drug was studied. Strontium ranelate was synthesized from citric acid via decarboxylation, esterification, cyclization, alkylation, hydrolysis and salification. The structure of strontium ranelate was confirmed by IR, ¹H-NMR, ¹³C-NMR and the total yield was 42.6% approx. The synthesis route was simple, low cost and could be used in industry. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0SDS of cas: 58168-20-0).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mixed-Linker Isoreticular Zn(II) Metal-Organic Frameworks as Bronsted Acid-Base Bifunctional Catalysts for Knoevenagel Condensation Reactions was written by Huang, Guo-Quan;Chen, Jun;Huang, Yong-Liang;Wu, Kun;Luo, Dong;Jin, Ji-Kang;Zheng, Ji;Xu, Shi-Hai;Lu, Weigang. And the article was included in Inorganic Chemistry in 2022.Application of 55490-87-4 This article mentions the following:

Multicomponent metal-organic frameworks (MOFs) have received an increasing amount of attention due to their potential to produce new topologies, pore metrics, and functionalities compared to MOFs with a single metal cluster and one organic linker. Herein, five isoreticular Zn MOFs were obtained by mixing two types of linear ditopic linkers in a one-pot solvothermal synthesis. Interestingly, in the resulting Zn MOFs a six-connected cyclic trinuclear Zn(II) cluster and an eight-connected linear trinuclear Zn(II) cluster coexist, leading to an uncommon (6,8)-connected network. Catalytic activities toward the solvent-free Knoevenagel reactions were observed for all of these MOFs. Further exptl. and computational studies suggest that they are Bronsted acid-base bifunctional catalysts. Through chem. modifications of dicarboxylate ligands, including their aromatic backbones and substituents, we have successfully implemented reticular chem. for the modulations of pore sizes, surface areas, and catalytic performances in a series of four-component isoreticular MOFs. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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 of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterogeneous cobalt catalysts for reductive amination with H₂: general synthesis of secondary and tertiary amines was written by Mao, Fei;Sui, Dejun;Qi, Zhengliang;Fan, Haipeng;Chen, Rizhi;Huang, Jun. And the article was included in RSC Advances in 2016.Reference of 10282-32-3 This article mentions the following:

Heterogeneous Co@NC catalysts were prepared, characterized and applied for the reductive amination of aldehydes and ketones with H₂ gas. The Co catalyst Co@NC (800-2 h) was found to be active and selective for the reductive amination of aldehydes and ketones using H₂ gas. Thus, general synthesis of secondary and tertiary amines was developed by the Co-catalyzed reductive amination with H₂ gas, and various secondary and tertiary amines was obtained in high yields. Moreover, a practical synthesis of N-substituted isoindolinones was also presented by a one step process with the Co@NC (800-2 h) catalyst. The Co@NC (800-2 h) catalyst was reusable at least five times without evident loss of activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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 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.Reference of 10282-32-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new and practical method for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones was written by Camarasa, Marta;Barnils, Christian;Puig de la Bellacasa, Raimon;Teixido, Jordi;Borrell, Jose I.. And the article was included in Molecular Diversity in 2013.Quality Control of 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

A one step general synthetic method for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione derivatives was described. This methodol. is based on treating a 2-aryl-substituted acrylate with a 6-amino-4(3H)-pyrimidinone derivative in the presence of a base under microwave irradiation conditions. The resulting pyrido[2,3-d]pyrimidine derivatives present an aryl substituent at position C6, precisely the one directly related to the biol. activity of such heterocyclic compounds These protocols were extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylate derivatives but with lower yields. The synthesis of the target compounds was achieved by a reaction of 2,6-diamino-4(3H)-pyrimidinone with 浼?(methylene)benzeneacetic acid Me ester derivatives (acrylate esters), 浼?methylene-1-naphthaleneacetic acid Me ester, 2-methyl-2-propenoic acid Me ester. 6-Amino-2-(methylthio)-4(3H)-pyrimidinone was also a suitable starting material. The title compounds thus formed included 2-amino-5,8-dihydro-6-(phenyl)pyrido[2,3-d]pyrimidine-4,7(3H,6H)-dione (I) and related substances. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Quality Control of 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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. 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.Quality Control of 2-(2,6-Dibromophenyl)acetonitrile

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

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