Author: Jessica.F

Rhodium-Catalyzed Anti-Markovnikov Hydrohydrazination of Terminal Alkynes with N-Alkyl- and N,N-Dialkylhydrazines was written by Fukumoto, Yoshiya;Ohmae, Akihiro;Hirano, Masaya;Chatani, Naoto. And the article was included in Asian Journal of Organic Chemistry in 2013.Product Details of 4435-14-7 This article mentions the following:

The anti-Markovnikov addition of hydrazines to terminal alkynes in the presence of [TpRh(C₂H₄)₂]/P(2-furyl)₃ (Tp=trispyrazolylborate) as a catalyst system has been developed. N-alkyl- and N,N-dialkyl-substituted hydrazines are applicable to this highly regioselective hydrohydrazination, which affords aldimine-type hydrazine derivatives In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Product Details of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° 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 π 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. Product Details of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions was written by Kampmann, Sven S.;Skelton, Brian W.;Wild, Duncan A.;Koutsantonis, George A.;Stewart, Scott G.. And the article was included in European Journal of Organic Chemistry in 2015.Synthetic Route of C14H12N2 This article mentions the following:

In this report we describe the design and preparation of a new air-stable nickel phosphite based catalyst for unique C-N bond forming processes. Specifically, (BINAP)Ni[P(OPh)₃]₂, is presented as an effective catalyst for a range of amination reactions between aryl halides and primary alkylamines. The results are supported by relevant kinetic studies, DFT calculations and a catalytic cycle indicating possible reaction intermediates. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Synthetic Route of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Imidazolium-based phosphinite ionic liquid (IL-OPPh₂) as reusable catalyst and solvent for the Knoevenagel condensation reaction was written by Valizadeh, Hassan;Gholipour, Hamid. And the article was included in Synthetic Communications in 2010.Electric Literature of C14H14N2O2 This article mentions the following:

A task-specific ionic liquid (IL), which bears a weak Lewis base (OPPh₂) in an imidazolium cation, efficiently catalyzed the Knoevenagel condensation of aryl aldehydes with H₂C(CN)₂, H₂C(CO₂Me)₂, H₂C(CO₂Et)₂, and NCCH₂CO₂Et. This IL played a dual role as both the reaction medium and also catalyst, and it could be easily recovered and reused in several runs. Satisfactory results were obtained with good yields, short reaction time, and simplicity in the exptl. procedure. A variety of coumarin derivatives were synthesized in this procedure. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Electric Literature of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° 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 π bond in the triple bond. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and properties of several nitrile analogs of bis(2-chloroethyl)amine was written by Rodionov, P. V.;Rapp, L. B.;Nikolaeva, S. V.. And the article was included in Fiziologicheski Aktivnye Veshchestva (1966-1992) in 1973.Recommanded Product: 7528-78-1 This article mentions the following:

Reaction of RN(CH2CH2Cl)2 (R = NCCH2CH2, m-BrC6H4CH2, p-FC6H4CH2, m-, p-, and o-MeC6H4CH2) with NaCN-EtOH gave a mixture of RN(CH2CH2CN)2 and RN(CH2CH2CN)CH2CH2OEt. The LD50 of (NCCH2CH2)3N in mice (s.c.) was 880 mg/kg; the maximum transfer dose was 300 mg/kg. 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. 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.Recommanded Product: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of antipodagra febuxostat was written by Liu, Xiao-zu;Liu, Pei-jun;Yuan, Ze-li;Hu, Qing-hong. And the article was included in Jingxi Huagong in 2014.Recommanded Product: 5203-15-6 This article mentions the following:

Febuxostat was synthesized from 4-hydroxybenzonitrile via alkylation, bromination, thioformylation, cyclization, cyanation, and hydrolysis. In the improved process, a LiCl-promoted thioformylation needed less time as well as avoided the use of strong acidic conditions. With the catalysis of trace Pd (OAc)₂, a cyano group was smoothly installed in the presence of K₄ [Fe (CN)₆] without anhydrous anaerobic operation. Non-toxic K₄ [Fe (CN)₆] was used advantageously compared to toxic cyanide sources. The total yield was as high as 64.3%. The structure was confirmed by m.p., ¹H-NMR, ¹³C-NMR and ESI-MS. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Recommanded Product: 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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.Recommanded Product: 5203-15-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives was written by Mahdavi, Behnam;Hosseyni-Tabar, Seyed Mahmood;Rezaei-Seresht, Esmail;Rezaei-Seresht, Hasan;Falanji, Farahnaz. And the article was included in Journal of the Iranian Chemical Society in 2020.Formula: C8H8N2S This article mentions the following:

Gallic acid (GA) and its benzamide derivatives have a wide variety of biol. activities, such as antimicrobial, antioxidant, anticancer. In this study, we have reported the synthesis of some new hybrid compounds comprised of the 2-aminothiophene and GA moieties and evaluation of their cytotoxic activities against HeLa (cervical cancer), HCT116 (human colon cancer), and FT (fibroblast) cell lines as well as antimicrobial activities against some Gram-pos. and Gram-neg. bacteria. The reaction of some 2-aminothiophene derivatives (previously prepared from the Gewald reaction) with galloyl chloride having the acetylated hydroxyl groups and the subsequent deprotection of the hydroxyl groups gave the desired hybrid compounds Then, the antimicrobial activity of the compounds was evaluated using disk diffusion and min. inhibitory concentration assays. Finally, the MTT assay was carried out to evaluate the cytotoxicity of the synthesized compounds on the mentioned cell lines. The structure of the synthesized compounds was elucidated by conventional spectroscopic methods such as NMR, FT-IR, and UV-Vis spectroscopy. All compounds prevented the growth of Staphylococcus coagulase more than the pos. control of chloramphenicol, and one compound was more sensitive to the growth of Klebsiella pneumonia compared to the standard antibiotic. All compounds showed acceptable activity against cancer cells. The highest activity was observed against HeLa with an IC50 value of 3.2 μg/mL for compound 3d and against HCT116 with IC50 of 59.4 μg/mL for 3b. The high anticancer activity of compound 3d against HeLa allows us to consider it as a good lead compound for the development of new potent anticancer agents for the treatment of cervical cancer. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-activity relationships in the formation of amides from substituted N-benzylanilines was written by Ulgen, M.;Gorrod, J. W.;Barlow, D.. And the article was included in Xenobiotica in 1994.HPLC of Formula: 10282-32-3 This article mentions the following:

The in vitro hepatic microsomal metabolism of certain substituted N-benzylanilines was studied in the male hamster to establish the mechanism(s) and process(es) involved in the formation of the corresponding amides. N-benzyl-2,4,6-trihalogeno, N-benzyl-4-cyano- and N-benzyl-4-nitroanilines were only metabolized by N-debenzylation. However, N-benzyl-4-methyl- and N-benzyl-2,4,6-trimethylanilines gave rise to both the corresponding amide and nitrone metabolites together with dealkylation products. These latter two substrates also produced hydroxymethyl metabolites as major products. Metabolism of N-(2,4,6-trimethylbenzyl)aniline also led to the formation of an amide metabolite. The dealkylation products, the corresponding imine and an unknown metabolite, probably an hydroxylated products were also detected with this substrate. N-(2,4-dichlorobenzyl) and N-(2,6-dichlorobenzyl)anilines yielded the corresponding nitrone metabolites; but no amide metabolite was detected. Oxidative dealkylation leading to the formation of the corresponding primary anilines and aldehydes, together with para hydroxylation of aniline rings, were established as major routes of metabolism for both compounds Similarly, neither N-(2,4,6-trifluorobenzyl) nor N-(4-nitrobenzyl)anilines produced any amide metabolite although dealkylation products were detected. The pattern of amide formation observed for these N-benzylsubstituted anilines is discussed in terms of the steric and electronic effects of their aromatic substituents. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 10282-32-3).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Progress against Escherichia coli with the Oxazolidinone Class of Antibacterials: Test Case for a General Approach To Improving Whole-Cell Gram-Negative Activity was written by Takrouri, Khuloud;Cooper, Harold D.;Spaulding, Adnrew;Zucchi, Paula;Koleva, Bilyana;Cleary, Dillon C.;Tear, Westley;Beuning, Penny J.;Hirsch, Elizabeth B.;Aggen, James B.. And the article was included in ACS Infectious Diseases in 2016.Name: 2-Bromo-4-hydroxybenzonitrile This article mentions the following:

Novel antibacterials with activity against the Gram-neg. bacteria associated with nosocomial infections, including Escherichia coli and other Enterobacteriaceae, are urgently needed due to the increasing prevalence of multidrug-resistant strains. A major obstacle that has stalled progress on nearly all small-mol. classes with potential for activity against these species has been achieving sufficient whole-cell activity, a difficult challenge due to the formidable outer membrane and efflux barriers intrinsic to these species. Using a set of compound design principles derived from available information relating physicochem. properties to Gram-neg. entry or activity, we synthesized and evaluated a focused library of oxazolidinone analogs, a currently narrow spectrum class of antibacterials active only against Gram-pos. bacteria. In this series, we have explored the effectiveness for improving Gram-neg. activity by identifying and combining beneficial structural modifications in the C-ring region. We have found polar and/or charge-carrying modifications that, when combined in hybrid C-ring analogs, appear to largely overcome the efflux and/or permeability barriers, resulting in improved Gram-neg. activity. In particular, those analogs least effected by efflux and the permeation barrier had significant zwitterionic character. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Name: 2-Bromo-4-hydroxybenzonitrile).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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. 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.Name: 2-Bromo-4-hydroxybenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3-Amino-2,1-benzisothiazole. Synthesis of some chloro and trifluoromethyl derivatives was written by Gray, J.;Waring, D. R.. And the article was included in Journal of Heterocyclic Chemistry in 1980.Product Details of 53312-77-9 This article mentions the following:

7-Chloro-, 4,7-dichloro-, 5- and 7-(trifluoromethyl), 5-chloro-6-(trifluoromethyl)- and 5-chloro-7-(trifluoromethyl)-3-amino-2,1-benzisothiazoles were prepared Preparative details are included for a number of precursors to the benzisothiazoles which have not previously been described. Visible spectra of some azo dyes prepared from the title compounds with a selected coupler are discussed with reference to substituent effects. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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).Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9-Amino-5,7-dibromo-1,2,3,4-tetrahydroacridine hemihydrate was written by Celik, Ismail;Akkurt, Mehmet;Ekiz, Makbule;Okten, Salih;Tutar, Ahmet;Ersanli, Cem Cuneyt. And the article was included in IUCrData in 2017.Safety of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The asym. unit of the title compound, C₁₃H₁₂Br₂N₂·0.5H₂O, includes two mols. of 5,7-dibromo-1,2,3,4-tetrahydroacridin-9-amine and one water mol. In the crystal, C-H···O, N-H···N, N-H···O and O-H···N hydrogen bonds connect the mols., forming a two-dimensional network parallel to (010). The two-dimensional sheets are further assembled into a three-dimensional structure through C-H···π and π-π stacking interactions [centroid-centroid distance = 3.719 (2) Å]. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Safety of 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Safety of 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts