Author: Jessica.F

The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride was written by Blay, Gonzalo;Cardona, Luz;Garcia, Begona;Lahoz, Luisa;Pedro, Jose R.. And the article was included in Tetrahedron in 1996.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Sodium hydrogen telluride reacts chemoselectively with α,β-unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to give the corresponding saturated nitriles with good yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Safety of 2-Cyclohexylacetonitrile

Referemce:
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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives using high-speed vibration milling was written by Xu, Fang;Li, Yujin;Xu, Fengshuang;Ye, Qing;Han, Liang;Gao, Jianrong;Yu, Wubin. And the article was included in Journal of Chemical Research in 2014.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives e.g., I via one-pot cyclo-condensation of various ketones, malononitrile with elemental sulfur employing high-speed vibration milling with diethylamine as the catalyst was developed. The main advantages of this method are short reaction times, facile conditions, good yields, use of inexpensive catalyst and environmental friendly conditions. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of a Potent and Selective PI3Kδ Inhibitor (S)-2,4-Diamino-6-((1-(7-fluoro-1-(4-fluorophenyl)-4-oxo-3-phenyl-4H-quinolizin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile with Improved Pharmacokinetic Profile and Superior Efficacy in Hematological Cancer Models was written by Shukla, Manojkumar R.;Patra, Sukanya;Verma, Mahip;Sadasivam, Gayathri;Jana, Nirmal;Mahangare, Sachin J.;Vidhate, Prashant;Lagad, Dipak;Tarage, Anand;Cheemala, Murthy;Kulkarni, Chaitanya;Bhagwat, Shankar;Chaudhari, Vinod D.;Sayyed, Majid;Pachpute, Vipul;Phadtare, Ramesh;Gole, Gopal;Phukan, Samiron;Sunkara, Brahmam;Samant, Charudatt;Shingare, Manisha;Naik, Aditya;Trivedi, Sneha;Marisetti, Ajit Kumar;Reddy, Madhusudhan;Gholve, Milind;Mahajan, Nilesh;Sabde, Sudeep;Patil, Vinod;Modi, Dipak;Mehta, Maneesh;Nigade, Prashant;Tamane, Kaustubh;Tota, Swati;Goyal, Hemant;Volam, Harish;Pawar, Shashikant;Ahirrao, Prajakta;Dinchhana, Lal;Mallurwar, Sadanand;Akarte, Atul;Bokare, Anand;Kanhere, Rupesh;Reddy, Neetinkumar;Koul, Sarita;Dandekar, Manoj;Singh, Minakshi;Bernstein, Peter R.;Narasimham, Lakshmi;Bhonde, Mandar;Gundu, Jayasagar;Goel, Rajan;Kulkarni, Sanjeev;Sharma, Sharad;Kamboj, Rajender Kumar;Palle, Venkata P.. And the article was included in Journal of Medicinal Chemistry in 2020.Application of 60025-09-4 This article mentions the following:

PI3Kδ inhibitors have been approved for B-cell malignancies like CLL, small lymphocytic lymphoma, and so forth. However, currently available PI3Kδ inhibitors are nonoptimal, showing weakness against at least one of the several important properties: potency, isoform selectivity, and/or pharmacokinetic profile. To come up with a PI3Kδ inhibitor that overcomes all these deficiencies, a pharmacophoric expansion strategy was employed. Herein, we describe a systematic transformation of a “three-blade propeller” shaped lead, 2,3-disubstituted quinolizinone 11, through a 1,2-disubstituted quinolizinone 20 to a novel “four-blade propeller” shaped 1,2,3-trisubstituted quinolizinone 34. Compound 34 (I)has excellent potency, isoform selectivity, metabolic stability across species, and exhibited a favorable pharmacokinetic profile. Compound 34 also demonstrated a differentiated efficacy profile in human germinal center B and activated B cell-DLBCL cell lines and xenograft models. Compound 34 qualifies for further evaluation as a candidate for monotherapy or in combination with other targeted agents in DLBCLs and other forms of iNHL. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Application of 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. 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.Application of 60025-09-4

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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

Substituent Effects on the Thermochemistry of Thiophenes. A Theoretical (G3(MP2)//B3LYP and G3) Study was written by Notario, Rafael;Temprado, Manuel;Roux, Maria Victoria;Liebman, Joel F.. And the article was included in Journal of Physical Chemistry A in 2012.Name: 3-Methylthiophene-2-carbonitrile This article mentions the following:

Very good linear correlations between exptl. and calculated enthalpies of formation in the gas phase (G3(MP2)//B3LYP and G3) for 48 thiophene derivatives were obtained. These correlations permit a correction of the calculated enthalpies of formation to estimate more reliable exptl. values for the enthalpies of formation of substituted thiophenes, check the reliability of exptl. measurements, and also predict the enthalpies of formation of new thiophenes that are not available in the literature. Also, the difference between the enthalpies of formation of isomeric thiophenes with the same substituent in positions 2 and 3 of the ring was analyzed. Likewise, a comparison of the substituent effect in the thiophene and benzene rings was established. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Name: 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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.Name: 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

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

Referemce:
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

Referemce:
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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts