Category: nitriles-buliding-blocks

Synthesis of 5-[bis(carboxymethyl)amino]-2-carboxy-4-cyano-3-thiopheneacetic acid strontium salt (strontium ranelate) was written by Wang, Qiang;Pan, Hongjuan;Yuan, Zhedong. And the article was included in Zhongguo Yiyao Gongye Zazhi in 2007.Related Products of 58168-20-0 This article mentions the following:

A method for the synthesis of the title compound [i.e., distrontium ranelate, 5-[bis(carboxymethyl)amino]-2-carboxy-4-cyano-3-thiopheneacetic acid strontium salt] is reported here. Strontium ranelate (a bone formation stimulant) was synthesized from di-Et 1,3-acetonedicarboxylate [i.e., 3-oxopentanedioic acid 1,5-di-Et ester ] by a cyclization with sulfur and malononitrile, condensation with Et chloroacetate to give 5-[N,N-bis(ethoxycarbonylmethyl)amino]-4-cyano-3-ethoxycarbonylmethyl-2-thiophenecarboxylic acid Et ester, which was subjected to alk. hydrolysis with strontium hydroxide. The overall yield was 34%. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Related Products of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Related Products of 58168-20-0

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Base-mediated cascade amidination/N-alkylation of amines by alcohols was written by Zhang, Chunyan;Liang, Zuyu;Lu, Fenghong;Jia, Xiaofei;Zhang, Guoying;Hu, Mao-Lin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Electric Literature of C14H12N2 This article mentions the following:

A base-mediated cascade amidination/N-alkylation reaction of amines by alcs. was developed. For the first time, nitriles was identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, ¹⁵N labeled amine and was scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Electric Literature of C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Radical C-H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide was written by Dix, Stefan;Golz, Paul;Schmid, Jonas R.;Riedel, Sebastian;Hopkinson, Matthew N.. And the article was included in Chemistry – A European Journal in 2021.Computed Properties of C8H4F3NO This article mentions the following:

Herein, bis(trifluoromethyl)peroxide (BTMP, CF₃OOCF₃) as a practical and efficient trifluoromethoxylating reagent, which easily accessible from inexpensive bulk chems. was introduced. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which was previously prepared via multi-step approaches. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Computed Properties of C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Computed Properties of C8H4F3NO

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Some amine derivatives of acrylonitrile was written by Wiedeman, O. F.;Montgomery, W. H.. And the article was included in Journal of the American Chemical Society in 1945.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

CH₂:CHCN (I) (12, 000 cc.), added dropwise to 6500 cc. 28% NH₄OH at 30°, gives 1.7% (of the I used) of NCCH₂CH₂NH₂ (II), 88.5% of NH(CH₂CH₂CN)₂ (III), and 6% of N(CH₂CH₂CN)₃ (IV), m. 99°; 880 cc. of I, and 500 cc. NH₄OH give 5.8% of II, 83.5% of III, and 1% of IV; 6000 cc. of I and 36, 000 cc. NH₄OH give 23.9% of II, 58.9% of III, and 3.3% of IV. Many samples of IV, which remained unchanged at room temperature for several months, decomposed within 24 h. for no apparent reason; no effective stabilizer was found and CO₂ apparently accelerated decomposition III is quite stable but some decomposition occurs on distillation at 140-60°/2-5 mm. IV is recovered from the residue of the vacuum distillation of II and III by extraction with hot H₂O. Catalytic reduction of II in lots of 5-10 mol in the presence of 1.1 mol of anhydrous NH₃ and 2-3 g. Raney Ni (per mole of amine) at pressures of 50-250 atm. for 5-10 h. at 90-125° gives 54% of NH₂(CH₂)₃NH₂ (V), 12% of (H₂NCH₂CH₂CH₂)₂NH (VI), b_2-3 100°, d²⁰ 0.9307, d²⁵ 0.9268, n_D²⁵ 1.4910, and 3% of (H₂NCH₂CH₂CH₂)₃N (VII), b_2-3 140-50°, d²⁰ 0.9591, d²⁵ 0.9552, n_D²⁵ 1.4910. III gives 14% of V, 58% of VI, and 13% of VII. A mixture of 30% II, 65% III, and 4% IV gives 28% of V, 42% of VI, and 13% of VII. I and (CH₂)₂O give (NCCH₂CH₂)₂O, b_2-3 140°, d²⁰ 1.0497, d²⁵ 1.0457, n_D²⁵ 1.4404; reduction in the presence of NH₃ at 110-15° and 100 atm. for 2 h. yielded 25-30% of low-boiling impurities (some PrNH₂), 35-40% of H₂N(CH₂)₃OH, b_2-3 60°, d²⁰ 0.9832, d²⁵ 0.9794, n_D²⁵ 1.4597, and 20% of (H₂NCH₂CH₂CH₂)₂O, b₃ 130-40°, d²⁰ 0.9723, d²⁵ 0.9685, n_D²⁵ 1.4780; the residue was 15%. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Trigonal-Bipyramidal Copper(II) Complexes with Symmetric and Unsymmetric Tripodal Tetramine Ligands was written by Dittler-Klingemann, Andreas M.;Hahn, F. Ekkehardt. And the article was included in Inorganic Chemistry in 1996.Quality Control of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The syntheses of the aliphatic tripodal tetramine ligands N(CH₂CH₂CH₂NH₂)₃ (1), N[(CH₂CH₂CH₂NH₂)₂(CH₂CH₂NH₂)] (2), and N[(CH₂CH₂CH₂NH₂)(CH₂CH₂NH₂)₂] (3) are reported. The tripodal N₄– ligands 1–3 react with Cu(OH)₂ in H₂O to give blue Cu(II) complexes. Addition of NH₄PF₆ to such solutions yields [Cu(N₄)(NH₃)](PF₆)₂ [4; N₄ = 1, 4a; N₄ = 2, 4b; N₄ = 3, 4c]. The mol. structures of complexes 4a–c were determined by x-ray diffraction. All three complexes can be crystallized from H₂O. Selected crystallog. details are as follows 4a [4b] {4c}: formula C₉H₂₇CuF₁₂N₅P₂ [C₈H₂₅CuF₁₂N₅P₂] {C₇H₂₃CuF₁₂N₅P₂}, M = 558.82 [544.79] MLL {530.76} amu, monoclinic [monoclinic] {orthorhombic}, space group P2₁/c [C2/c] {P2₁2₁2}, a = 8.9519(14) [30.181(6)] {15.075(5)} Å, b = 16.803(3) [8.914(3)] {12.2939(14)} Å, c 13.834(2) [14.253(4)] {10.064(2)} , β = 94.183(12) [93.76(2)] {90.0}°, V = 2075.3(10) [3826(3)] {1865.2(12)} ų, Z = 4 [8] {4}, R = 5.10 [3.42] {4.32}, R_w = 6.67 [5.12] {5.23} for 2480 [2137] {1533} absorption corrected structure factors F_o² ≥ 3σ(F_o²) and 262 [255] {245} refined parameters. The complex dications in 4a–c exhibit a trigonal-bipyramidal geometry with the tertiary N of the tripodal ligand and the NH₃ N in the axial positions. Complexes with the unsym. ligands 2 and 3 possess both five and six membered chelate rings. Depending on the ligand, the size of the cavity for the NH₃ ligand increases from 4a to 4c. This leads to a shortening of the Cu-NH₃ bond length with the shortest bond of this type observed for 4c. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Quality Control of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Modular Continuous Flow Synthesis of Imatinib and Analogues was written by Fu, Wai Chung;Jamison, Timothy F.. And the article was included in Organic Letters in 2019.Electric Literature of C12H14N2O This article mentions the following:

A modular continuous flow synthesis of imatinib (I) and analogs is reported. Structurally diverse imatinib analogs are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidation modules each exhibit a broad scope with good to excellent yields. Overall, the method described does not require solvent switches, in-line purifications, or packed-bed apparatuses due to the judicious manipulation of flow setups and solvent mixtures In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Electric Literature of C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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. Electric Literature of C12H14N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

CNDO/2 calculations of molecules. 3. Ionization potential and charge distribution was written by Koppel, I.;Molder, U.. And the article was included in Organic Reactivity (Tartu) in 1981.Recommanded Product: 7528-78-1 This article mentions the following:

For several classes of aliphatic compounds, (e.g., ether, amines), a linear relation is established between ionization energy of the electron localized on a certain atom and semiempirical CNDO/2 charges on the latter. The charge distribution was calculated according to the Mulliken procedure. The correction for the intramol. Madelung potential was introduced into the valence shell ionization potentials. A method for the determination of the ionization potential of the lone pair from photoelectron spectra was suggested. The linearity between CNDO/2 and ab initio (STO-3G and 4-31G basis sets) charge densities was found. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 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).Recommanded Product: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterocyclic Meisenheimer complexes: kinetic and equilibrium data for methoxide ion attack on various disubstituted 2,4-Y,Z-thiophenes and -selenophenes in methanol was written by Terrier, Francois;Chatrousse, Alain-Pierre;Paulmier, Claude. And the article was included in Journal of Organic Chemistry in 1979.Category: nitriles-buliding-blocks This article mentions the following:

The stabilities of I (R, R¹ = NO₂, NO₂; CN, NO₂; NO₂, CN; X = Se, S) decreased in the stated order of R, R¹ and of X, but different trends were found in kinetic studies. II (R = CN; R¹ = NO₂; X = Se, S) reacted differently with MeO^– than the other II. An ortho-like NO₂ group may affect nucleophilic substitution more than a para-like NO₂ group. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Category: nitriles-buliding-blocks).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)-H Bonds with Anilines was written by Song, Yan-Ling;Li, Bei;Xie, Zhen-Biao;Wang, Dan;Sun, Hong-Mei. And the article was included in Journal of Organic Chemistry in 2021.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Iron-catalyzed oxidative amination of benzylic C(sp³)-H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) has been realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr₄] (1,3-di-tert-butylimidazolium iron tetrabromide) showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr₄] (1,3-bis(pyrimidin-2-yl)imidazolium iron tetrabromide) was more efficient for EDG-substituted anilines. This work provides an alternative access to benzylamines, e.g., RN(R¹)CH₂Ph [R = 4-O₂NC₆H₄, 2-pyrimidinyl, 8-isoquinolinyl, etc., R¹ = H, Me,], with advantages of both a wide substrate scope and iron catalysis. 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 carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent was written by Gallardo-Macias, Ricardo;Kumar, Pradeep;Jaskowski, Mark;Richmann, Todd;Shrestha, Riju;Russo, Riccardo;Singleton, Eric;Zimmerman, Matthew D.;Ho, Hsin Pin;Dartois, Veronique;Connell, Nancy;Alland, David;Freundlich, Joel S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Recommanded Product: 37812-51-4 This article mentions the following:

The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biol. profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019-0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC₅₀ = 40- > 120 μM) towards Vero cells. Significant improvements in mouse liver microsomal stability and mouse pharmacokinetic profile were realized by introduction of an α,α-dimethylbenzyl moiety. Among these compounds, JSF-4088 (I) is highlighted due to its in vitro antitubercular potency (MIC = 0.019 μM) and Vero cell cytotoxicity (CC₅₀ > 120 μM). The findings suggest a rationale for the continued evolution of this promising series of antitubercular small mols. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Recommanded Product: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Recommanded Product: 37812-51-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts