Category: 42137-24-6

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

Polarographic behavior of thiophene 5- and 4-nitro derivatives was written by Freidlin, G. N.;Glushkova, A. A.;Solop, K. A.. And the article was included in Zhurnal Analiticheskoi Khimii in 1979.Name: 4-Nitrothiophene-2-carbonitrile This article mentions the following:

The polarog. behavior of 20 2-substituted 4- and 5-nitrothiophene derivatives was examined A method is described for the simultaneous determination of isomers in binary and ternary systems in the 1 × 10^-5-2 × 10^-4 mol/L range. The derivatives can be presented as 2 series, which are described by Hammett equations for the E_1/2 values. Best results are obtained during the polarog. determination of nitration products by using acetate buffer solution (pH 3.7) and 40% EtOH. The standard deviation is 2-8%. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Name: 4-Nitrothiophene-2-carbonitrile).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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 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: 4-Nitrothiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts