Tag: 200-300

Synthesis of 2-Aryl/Heteroaryloxazolines from Nitriles under Metal- and Catalyst-Free Conditions and Evaluation of Their Antioxidant Activities was written by Garg, Parul;Chaudhary, Shweta;Milton, Marilyn D.. And the article was included in Journal of Organic Chemistry in 2014.Synthetic Route of C12H14N2O This article mentions the following:

The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and amino alcs. has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biol. active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. E.g., condensation of 3-BrC₆H₄CN with H₂NCH₂CH₂OH gave 83% 2-aryloxazoline derivative (I). An evaluation of the antioxidant properties using the DPPH (di-Ph picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Synthetic Route of C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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.Synthetic Route of C12H14N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid was written by Pingali, Subramanya R. K.;Madhav, Monika;Jursic, Branko S.. And the article was included in Tetrahedron Letters in 2010.Synthetic Route of C7H4Br2N2 This article mentions the following:

A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Synthetic Route of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Synthetic Route of C7H4Br2N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of 2-amino-4-aryl-3-cyano-6-methyl-5-ethoxycarbonyl-4H-pyrans was written by Shestopalov, Anatoliy M.;Niazimbetova, Zukhra I.;Evans, Dennis H.;Niyazymbetov, Murat E.. And the article was included in Heterocycles in 1999.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

A one-step electrochem. synthesis of the title compounds (I; R = Ph, 4-chlorophenyl, 3-nitrophenyl, 2-thienyl, 4-pyridyl) has been devised. The starting materials are aromatic and heteroaromatic aldehydes, malononitrile and Et acetoacetate. The overall reaction is catalyzed by electrogenerated base formed at a platinum cathode in acetonitrile. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solid phase synthesis of functionalized indazoles using triazenes – scope and limitations was written by Garcia, Ana Maria;Jung, Nicole;Gil, Carmen;Nieger, Martin;Braese, Stefan. And the article was included in RSC Advances in 2015.Electric Literature of C7H4Br2N2 This article mentions the following:

A modular synthesis of highly substituted indazoles via a strategy on solid supports was discussed. The heterocyclic nitrogen atoms originated from diazonium salts, being cleaved from triazene containing resins. The scope and limitations of this process was explored, considering especially the competitive occurrence of triazines and the cleavage of hydrolyzed and traceless side products. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Electric Literature of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Electric Literature of C7H4Br2N2

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Nitrile – Wikipedia,
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Iridium-Monodentate Phosphoramidite-Catalyzed Asymmetric Hydrogenation of Substituted Benzophenone N-H Imines was written by Hou, Guohua;Tao, Ran;Sun, Yongkui;Zhang, Xumu;Gosselin, Francis. And the article was included in Journal of the American Chemical Society in 2010.Reference of 62584-32-1 This article mentions the following:

Homogeneous asym. hydrogenation of unprotected benzophenone N-H imines using Ir-(S)-N-benzyl-N-methyl-MonoPhos as a catalyst provides chiral diarylmethylamines in 80-96% yield with enantioselectivities up to 98% ee (18 examples) for substituted substrates. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-(trifluoromethyl)benzonitrile (cas: 62584-32-1Reference of 62584-32-1).

2-Chloro-3-(trifluoromethyl)benzonitrile (cas: 62584-32-1) 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.Reference of 62584-32-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrophoretic migration imaging process was written by VanAllan, J. A.;Rossi, L. J.;Bloom, M. S.;Regan, M. T.;Wright, H. E.;Kaukeinen, J. Y.. And the article was included in Research Disclosure in 1978.Product Details of 55490-87-4 This article mentions the following:

Twenty-five photosensitive compounds having the general structure Z(CH:CRR¹)_n where Z is phenylene, naphthylene, anthracenyl, anthracenediyl, or dibenzothiendiyl, n = 1 or 2, and R and R¹ are H, CN, alkylsulfonyl, alkylcarbonyl, arylcarbamoyl, cyanoaryl, arylcarbonyl, or together form an substituted or unsubstituted ring are described for use in electrophoretic imaging. Thus, a dispersion (containing Isopar G 2.2, Solvesso 100 1.3, Piccotex 100 1.4, and lauryl methacrylate-Li methacrylate-methacrylic acid-vinyltoluene polymer 0.1 g) 5 and 5,5′-(9,10-anthracenediyldimethylidyne)bis[3,4-di(p-nitrophenyl)furan-2-one] 0.045 g were milled with stainless steel balls 12 g for 3 h and then evaluated to show a useful level of photosensitivity. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Product Details of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 55490-87-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Imidoyl chloride mediated one-pot synthesis of 3-electron withdrawing group substituted indoles was written by Zhan, Linjun;Hu, Wei;Wang, Mei;Huang, Bin;Long, Yaqiu. And the article was included in Huaxue Xuebao in 2021.SDS of cas: 67197-53-9 This article mentions the following:

Indole scaffold is widely present in pharmaceutical and pesticide products, dyes and natural products. The indole skeleton substituted by the electron withdrawing group at position 3 is an important class of bioactive indole derivatives Among them, 3-cyanoindole is a key module in the construction of privileged scaffold-based combinatory library and diversity-oriented synthesis for drug discovery. For these reasons, the design and synthesis of these scaffolds have received considerable attention in organic synthesis and have been extensively studied. However, the cyano group on the indole was introduced directly in previously reported methods. Due to the high toxicity of cyanide, the application of these reactions is limited. Imidoyl chloride, a highly reactive synthon, which was successfully used as a module for the construction of quinolones, quinazolines, benzimidazoles and other drug-like privileged scaffolds by our group. By making use of the imidoyl chloride as the active intermediate to mediate a cascade reaction to form the heterocycle, we developed a new one-pot synthesis to construct the 3-cyano or carboxylate-indole derivatives The reaction proceeded via two sequential steps: initial formation of imidoyl chloride starting from N-substituted arylamide and thionyl chloride, followed by 2-bromo-arylnitrile carbanion nucleophilic addition, elimination and Ulmann reaction. This synthetic methodol. is featured with cheap and readily available starting materials, high reaction yields, high functional group tolerance and broad substrate scope. This reaction is a direct synthesis not requiring prefunctionalization, and highly atom- and step-economic. It’s worth noting that it’s the first time building 3-cyanoindole scaffold commenced with the substrates bearing cyano group, which is of great importance for avoiding potential safety hazards. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9SDS of cas: 67197-53-9).

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–C bond formation or by dehydration of primary carboxamides. 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.SDS of cas: 67197-53-9

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO₂ and deacetalization-Knoevenagel condensation was written by Lv, Hongxiao;Fan, Liming;Chen, Hongtai;Zhang, Xiutang;Gao, Yanpeng. And the article was included in Dalton Transactions in 2022.Application of 55490-87-4 This article mentions the following:

The rare combination of Ba(II) (5s) and Zn^II (3d) in the presence of the structure-oriented TDP⁶– ligand generated the nanochannel-based hybrid material {[(CH₃)₂NH₂]₂[BaZn(TDP)(H₂O)]·DMF·5H₂O}_n (NUC-51, H₆TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochem. characteristics such as nanoscopic channels, high porosity, large sp. surface area and high heat/water-resistance. This is the first 3D [Ba^IIZn^II(CO₂)₆(H₂O)]-based nano-porous host framework, whose activated state NUC-51a possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn²⁺ ions, 7-coordinated Ba²⁺ ions, uncoordinated carboxyl oxygen atoms and N_pyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO₂ at 55°C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70°C. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Application of 55490-87-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solubility and solution thermodynamics of ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate in nine organic solvents at evaluated temperatures was written by Han, Shuo;Meng, Long;Du, Cunbin;Xu, Jian;Cheng, Chao;Wang, Jian;Zhao, Hongkun. And the article was included in Journal of Chemical Thermodynamics in 2016.HPLC of Formula: 58168-20-0 This article mentions the following:

Knowledge of solubility for Et 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate (ACET) in different solvents is essential for its purification and further theor. studies. In this paper, the solubility of ACET in selected pure solvents, including methanol, ethanol, 1-butanol, n-propanol, isopropanol, toluene, Et acetate, acetonitrile and acetone were acquired by a high-performance liquid chromatog. (HPLC) at T = (273.15, 278.15, 283.15, 288.15, 293.15, 298.15, 303.15, 308.15, 313.15 and 318.15) K under pressure of 0.1 MPa. Generally, they obeyed the following order from high to low in different solvents: acetone > Et acetate > acetonitrile > methanol > ethanol > isopropanol > n-propanol > 1-butanol > toluene. The obtained solubility data of ACET in selected solvents were correlated by the van’t Hoff equation, modified Apelblat equation, λh equation, Wilson model and NRTL model. The correlated values of the five equations agreed well with the exptl. values and the Wilson model gives better correlation results than other models. Furthermore, the standard dissolution enthalpy and excess enthalpy for dissolution process of ACET were calculated from the exptl. solubility by using the van’t Hoff equation. The solubility values of ACET in different solvents and thermodn. relations would be invoked as fundamental data and models regarding the crystallization process of ACET. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0HPLC of Formula: 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–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.HPLC of Formula: 58168-20-0

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Spectrographic method for the detection of active methylene groups and synthesis of several styrene and stilbene derivatives. VII. Bromo derivatives of phenylacetonitrile was written by Areschka, Alex;Bruylants, Albert. And the article was included in Bulletin de la Societe Chimique de France in 1958.SDS of cas: 67197-53-9 This article mentions the following:

By the same methods as in the preceding abstract the order of decreasing acidity of the cyanomethyl group in Br derivatives of PhCH₂CN is 4-Br > 2,4-di-Br > 2-Br > 2,4,6-tri-Br > 2,6-di-Br. The rate of formation and yields of cyanostilbenes from these compounds and BzH (I) or p-Me₂NC₆H₄CHO (II) decrease in the order of decreasing acidity (Br location, aldehyde, reaction time in days, yield of cyanostilbene, and m.p. are given): 4-, I, 0, 99, 109-12°, 129-54.5° (geometric isomers); 4-, II, 0, 99, 193-3.5°; 2,4-, I, 45 min., 99, 141-2°; 2,4-, II, 1, 82, 126-7°; 2-, I, 1, 64, 71.5-2°; 2-, II, 1, 60, 137-9°; 2,4,6-, I, 8, 43, 132.8-144.8°; 2,4,6-, II, 8, 30, 164.5-5.5°; 2,6-, I, 8, 27, 118.5-20°; 2,6-, II, 8, 24, 187-8.5°. 2,4-Br₂C₆H₃CH₂CN, m. 83.5-4.5°, is prepared in 24% yield from 3-H₂NC₆H₄Me by acetylation, bromination, deacetylation, deamination, side chain bromination and cyanation, and the 2,6-di-Br isomer, m. 97-7.5°, in 15% yield from 4-O₂NC₆H₄CH₃ by bromination, reduction, deamination, side chain bromination and cyanation. A new synthesis of 2,4,6-Br₃C₆H₂CH₂CN from 3-O₂NC₆H₄CH₂CN by reduction, bromination, and deamination is given. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9SDS of cas: 67197-53-9).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts