Author: Jessica.F

Facile synthesis of nitriles from primary nitro compounds via nitrolic acids and their esters was written by Chang, Rae Kyu;Kim, Kyongtae. And the article was included in Tetrahedron Letters in 1996.Application of 4435-14-7 This article mentions the following:

The reactions of alkane- and arylalkanenitrolic acids esters with Bu₃SnH in the presence of a catalytic amount of AIBN in refluxing benzene afforded the corresponding nitriles in excellent yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application of 4435-14-7).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Studies on aromatic nitro compounds. V. A simple one-pot preparation of o-aminoaroylnitriles from some aromatic nitro compounds was written by Tomioka, Yukihiko;Ohkubo, Kimiko;Yamazaki, Motoyoshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Synthetic Route of C8H5F3N2 This article mentions the following:

The reactions of aromatic nitro compounds I, II (R = H, R¹ = NO₂), and III (R, R¹ = same, R² = CF₃, MeCO, PhCO, R³ = H ; R² = R³ = CF₃) with Et cyanoacetate and KOH in DMF followed by hydrolysis of the reaction mixture with HCl or NaOH gave the corresponding o-aminoaroylnitriles I–III (R = CN, R¹ = NH₂). Acetylation-cyclization reactions of the products were carried out. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Synthetic Route of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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 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.Synthetic Route of C8H5F3N2

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Nitrile – Wikipedia,
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Facile and efficient cyclization of anthranilonitrile to 2,4-dichloroquinazoline by bis(trichloromethyl) carbonate and catalytic amount triphenylphosphine oxide was written by Li, Zhenhua;Wu, Danli;Zhong, Weihui. And the article was included in Heterocycles in 2012.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

2,4-Dichloroquinazolines were synthesized by the cyclization of anthranilonitrile using bis(trichloromethyl)carbonate with the aid of catalytic amount of Ph₃PO at 120 °C. This method was also applied to the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine. The plausible mechanism was presented. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 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.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

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Nitrile – Wikipedia,
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Microwave-accelerated Gewald reaction. Synthesis of 2-aminothiophenes was written by Sridhar, Madabhushi;Rao, Rayankula Mallikarjuna;Baba, Nanduri H. K.;Kumbhare, Ravindra M.. And the article was included in Tetrahedron Letters in 2007.Recommanded Product: 70291-62-2 This article mentions the following:

Microwave-promoted synthesis of 2-aminothiophenes by multicomponent reactions of a ketone with an active nitrile and elemental sulfur under KF-alumina catalysis is described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 70291-62-2).

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

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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

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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

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Nitrile – Wikipedia,
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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

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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

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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

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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