Category: nitriles-buliding-blocks

A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase was written by Paul, Sima;Ghosh, Pritam;Roy, Partha. And the article was included in New Journal of Chemistry in 2020.Reference of 51473-74-6 This article mentions the following:

A coumarin based compound, 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (DCCO), was developed as a visual fluorescent chemodosimeter for selective detection of highly toxic phosgene gas. DCCO exhibits absorption bands at 330 nm and 425 nm. In the presence of phosgene, the absorbance at 330 nm increases and the peak at 425 nm is shifted to 420 nm with decreasing absorbance accompanying a color change from yellow to colorless. The fluorescence intensity of the probe at 483 nm is enhanced in the presence of phosgene (λ_ex = 425 nm) but nerve agents and other acid chlorides including trisphosgene could not induce any significant enhancement of the fluorescence. DCCO on interaction with phosgene is converted to the corresponding nitrile derivative, 7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile (DCC). The quantum yield was increased 13 fold on conversion from DCCO to DCC. The fluorescence enhancement was explained by the ICT mechanism, which was supported by theor. calculations It exhibits a rapid response for naked eye detection of phosgene. DCCO was used for the detection of phosgene in solution and the gas phase. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Reference of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Reference of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-Formylpyridyl Ureas as Highly Selective Reversible-Covalent Inhibitors of Fibroblast Growth Factor Receptor 4 was written by Knoepfel, Thomas;Furet, Pascal;Mah, Robert;Buschmann, Nicole;Leblanc, Catherine;Ripoche, Sebastien;Graus-Porta, Diana;Wartmann, Markus;Galuba, Inga;Fairhurst, Robin A.. And the article was included in ACS Medicinal Chemistry Letters in 2018.Electric Literature of C5H4N4 This article mentions the following:

As part of a project to identify FGFR4 selective inhibitors, scaffold morphing of a 2-formylquinoline amide hit identified series of 2-formylpyridine ureas (2-FPUs) with improved potency and physicochem. properties. In particular, tetrahydronaphthyridine urea analogs with cellular activities below 30 nM have been identified. Consistent with the hypothesized reversible-covalent mechanism of inhibition, the 2-FPUs exhibited slow binding kinetics, and the aldehyde, as the putative electrophile, could be demonstrated to be a key structural element for activity. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Electric Literature of C5H4N4).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 C5H4N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Equilibrium NH-acidity of substituted aminopyrimidines was written by Shkurko, O. P.;Terekhova, M. I.;Petrov, E. S.;Mamaev, V. P.;Shatenshtein, A. I.. And the article was included in Zhurnal Organicheskoi Khimii in 1981.Category: nitriles-buliding-blocks This article mentions the following:

The transmetalation method was used to determine the NH acidity (pK) of thirty-nine 2-, 4-, and 5-aminopyrimidines; the pK values ranged from 17.7 for 5-nitro-2-pyrimidinamine to 30.2 for 2-(dimethylamino)-5-pyrimidinamine. Comparison with the pK of aniline showed that the ring N atoms had an acidifying effect in the order 4-aza ≫ 2-aza > 3-aza. LFER of the pK vs. NMR chem. shifts, and inductive or resonance substituent constants were described. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Category: nitriles-buliding-blocks).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An improved synthesis of homoproline and derivatives was written by Shuman, Robert T.;Ornstein, Paul L.;Paschal, Jonathan W.;Gesellchen, Paul D.. And the article was included in Journal of Organic Chemistry in 1990.HPLC of Formula: 36057-44-0 This article mentions the following:

Homoproline derivatives I (R = 3-Me, 4-Me, 6-Me, 4-Et, 4-OMe, 4-CMe₃) were prepared from the corresponding pyridines II in 4 steps. A key step was the treatment of N-oxides III (R = same) with Me₃SiCN and Me₂NCOCl in CH₂Cl₂ to give nitriles IV (R = same). 5,6-Benzohomoprolines V (R¹ = H, Me) were also prepared In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0HPLC of Formula: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. HPLC of Formula: 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reactivity of 2-aminothiophenes. Application to synthesis of thieno[2,3-b]pyrroles was written by Wierzbicki, Michel;Cagniant, Denise;Cagniant, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1975.Name: Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Thienopyrroles I (R = H, Ac; R1 = OH, NH2; R2 = CH2CO2Et, Me; R3 = CO2Et, Ac) were prepared by treating the thiophenes II (R4 = H; R5 = CO2Et, CN) with BrCH2CO2Et and Dieckmann reaction of II (R4 = CH2CO2Et). I (R1 = OH) were alkylated with BrCH2CO2Et or acetylated. I (R2 = NH2) were acetylated and diazotized. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Name: Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Research in the heterocyclic series. VII. Orientation of nitro derivatives of α-substituted thiophenes, pyrroles, and N-methylpyrroles was written by Tirouflet, Jean;Fournari, Pierre. And the article was included in Bulletin de la Societe Chimique de France in 1963.COA of Formula: C5H2N2O2S This article mentions the following:

The ratios of the isomeric mono-NO₂ derivatives formed under various conditions from 2-substituted-thiophenes (I), pyrroles (II), and 1-methylpyrroles (III) were determined polarographically and found to be dependent on the nature of the α-substituent and the hetero atom. In the thiophene series, the substituent exerts a more pronounced effect than in the pyrrole series and the 1-methylpyrrole series. The N-methylation of pyrroles increases the reactivity of the β-position. The nitrations in the II and III series were performed by nitrating the appropriate heterocyclic substrate (1-4 g.) by the methods described previously (loc. cit.), pouring the mixture onto 10-50 g. ice, and then polarographing the solution (if necessary after the addition of AcOH or aqueous EtOH); the half-wave potentials were determined for the following I (2-substituent, pH, and half-wave potentials in neg. v. of the 5- and 4-NO₂ derivatives given): H, 3.1, 0.30, 0.40; NO₂, 3.1, 0.06, 0.13; CHO, 9.1, 0.35, 0.57 (at pH 4.2, the 5-NO₂ derivative showed 2 waves at -0.16 and -0.31 v., resp., and the 4-NO₂ derivative 1 at -0.34 v.); Ac, 10.2, 0.41, 0.61; CN, 3.1, 0.14, 0.29; CO₂H, 4.2, 0.23, 0.42. The same delta were determined for the following II (same data given): H, 3.1, 0.54, 0.67; NO₂, 2, 0.07, 0.18; CHO, 2, 0.15, 0.50; Ac, 3.1, 0.24, 0.51; CN, 3.1, 0.14, 0.29; CO₂H, 3.1, 0.31, 0.60. The same data were determined for the following III (same data given): H, 5.4, 0.59, 0.68; NO₂, 3.1, 0.08, 0.25; CHO, 10.2, 0.55, 0.76; Ac, 10.2, 0.60, 0.80; CN, 5.2, 0.37, 0.53; CO₂H, 3.1, 0.25, 0.52. The % content of the 4-NO₂ derivatives (IV) in the nitration products of the following I was determined polarographically (2-substituent and % IV given): H 5, NO₂ 80, CHO 75, Ac 52, CN 43, CO₂H 31, CH(OAe)₂ 14. The % content of the IV from the following II was determined (same data given): H 9, NO₂ 67, CHO 59, Ac 57, CN 42, CO₂H, 55. The % content of the IV from the following III was deed. (same data given): II 43, NO₂ 70, CHO 80, Ac 68, CN 65, CO₂H 68. The effect of various reaction media on the composition of the product was determined in a series of runs with I. 2-Thiophenecarboxaldehyde with HNO₃H₂SO₄ (free CHO group) yielded preferentially the 4-NO₂ derivative, while nitration in Ac₂O [CHO group present as CH(OAc)₂] favored the formation of the 5-NO₂ derivative In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6COA of Formula: C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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.COA of Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation and characterization of ZnO/nanoclinoptilolite as a new nanocomposite and studying its catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction was written by Javadi, Farzad;Tayebee, Reza. And the article was included in Microporous and Mesoporous Materials in 2016.Category: nitriles-buliding-blocks This article mentions the following:

The nanocomposite ZnO/nanoclinoptilolite (ZnO/NCP) was prepared and used as an efficient heterogeneous catalyst in the synthesis of 2-aminotiophene derivatives by Gewald reaction. The nanocomposite was prepared through impregnation of the nanoclinoptilolite (NCP) surface with zinc chloride solution through Zn²⁺ ion exchange, followed by calcination at 500° for 24 h. The synthesized nanocomposite was characterized by XRD, SEM, FESEM, FT-IR, ICP, and nitrogen adsorption/desorption isotherm. The obtained catalytic assays demonstrated that the catalytic activity of ZnO/NCP nanocomposite was increased with enhancing the amount of ZnO. Moreover, the prepared nanocomposite showed very good stability and reusability in the titled synthetic method under aerobic and mild conditions. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

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. 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. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Selective reduction of α,β-unsaturated nitriles with combined reducing agent bismuth chloride/sodium borohydride was written by Ren, Ping-Da;Shao, Dong;Dong, Ting-Wei. And the article was included in Youji Huaxue in 1997.Quality Control of 2-Cyclohexylacetonitrile This article mentions the following:

Bismuth chloride/sodium borohydride reacts chemoselectively with α,β-unsaturated nitriles in 95% ethanol to give the corresponding saturated nitriles with good yields. E.g., reduction of PhCH:CHCN with NaHBH₄/BiCl₃ in 95% EtOH at room temperature for 3 h gave 90% PhCH₂CH₂CN. The reduction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Quality Control of 2-Cyclohexylacetonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Diradical rearrangements. Part 211. An unusual 1,2-shift in a photochemically generated 1,3-diradical. Mechanistic and exploratory organic photochemistry. Part 151 was written by Zimmerman, Howard E.;Kamath, Ajit P.. And the article was included in Journal of the American Chemical Society in 1988.Electric Literature of C11H13NO This article mentions the following:

The triplet photochem. of 2,5-dianisyl-2,5-dimethyl-3-hexene was explored in a study of the behavior of diradical species occurring in the di-π-methane rearrangement. The penultimate species, the 1,3-diradical, closes more rapidly to cyclopropane product than the latter rearranges further. The photoproduct, 1-anisyl-2-(p-methoxycumenyl)-3,3-dimethylcyclopropane, undergoes a novel singlet rearrangement resulting from three-ring opening to a 1,3-diradical, followed by a 1,2-shift of the p-methoxycumenyl moiety. The diradical, 1-anisyl-2-(p-methoxycumenyl)-3,3-dimethyl-1,3-propanediyl (I), also underwent fragmentation to p-methoxycumenyl and 1-anisyl-3,3-dimethylallyl radicals as a minor process constituting 12%. The two products of the 1,2-shift of the p-methoxycumenyl group in I were 1,4-dianisyl-3,3,4-trimethyl-1-pentene and 4,5-dianisyl-2,5-dimethyl-2-hexene. This was the major reaction course of the singlet I. Crossover experiments were run using the bis(deuteriomethoxy)-labeled cyclopropane. Four percent crossover, resulting from disengagement of a p-methoxycumenyl radical and recombination, was observed The mechanism of the I 1,2-shift is discussed. The quantum yield for the diyl rearrangement was determined Crystal structures of several of the compounds were determined In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Electric Literature of C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.Electric Literature of C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitration of m-tolunitrile and identification of the products was written by Shi, Zhi-hao;Wei, Yun-yang;Qin, Tao;Mu, Fei-hu. And the article was included in Jingxi Huagong in 2005.HPLC of Formula: 64113-86-6 This article mentions the following:

Three nitro isomers of m-tolunitrile were obtained in 92% total yield via nitration of m-tolunitrile with concentrated nitric acid (≥98%) under the following conditions: n(m-tolunitrile):n(nitric acid) = 1:10, reaction time 2 h, reaction temperature 18 ∼ 20 °C and dropping nitric acid to m-tolunitrile in ice bath. Column chromatog. followed by recrystallization gave three pure isomers 5-cyano-2-nitrotoluene, 3-cyano-4-nitrotoluene and 3-cyano-2-nitrotoluene in 43%, 37% and 12% yield resp., based on m-tolunitrile. Structure of the pure isomers was characterized by IR, ¹HNMR and GS/MS. Regioselectivity of the nitration was discussed. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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.HPLC of Formula: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts