Nitriles-buliding-blocks

The electronic effect of the CN group in the aromatic and thiophene series was written by Tirouflet, J.. And the article was included in Bulletin de la Societe Chimique de France in 1958.Formula: C5H2N2O2S This article mentions the following:

A Hammet σ constant was determined for the CN group of nitrothiophenenitriles by polarographic reduction. Thiophene and POCl₃ in HCONMe₂ gave 2-thiophenecarboxaldehyde (I), which with HNO₃ gave 4-nitro-2-thiophenecarboxaldehyde, and with HNO₃ in Ac₂O gave the 5-NO₂ isomer. Oximation of the aldehyde followed by dehydration gave 2-cyano-4-nitro-thiophene (II) and the 5-NO₂ isomer (III), resp. The half-wave potentials of these compounds, determined at pH 3.10, permitted calculation of σ for the CN group of II and III as 0.69 and 1.0, resp., compared with 0.69 and 0.94 for Ac of the corresponding 2-Ac derivatives The difference in half-wave potentials was sufficient (0.14 v.) to allow quant. determination of II and III, particularly by oscillopolarography (the polarograms are illustrated). The product of nitration of 2-cyanothiophene was thus found to contain 42% II and 58% III. Nitration of 2-acetylthiophene and I gave 52% and 75%, resp., of the 4-NO₂ derivative A review of previous determinations of σ for the aromatic CN group is also included. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Formula: C5H2N2O2S).

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. 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.Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes was written by Kaki, Venkata Rao;Akkinepalli, Raghuram Rao;Deb, Pran Kishore;Pichika, Mallikarjuna Rao. And the article was included in Synthetic Communications in 2015.Application In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

A simple, efficient, and environmentally friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application In Synthesis 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. 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.Application In Synthesis of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent was written by Dohi, Toshifumi;Ito, Motoki;Yamaoka, Nobutaka;Morimoto, Koji;Fujioka, Hiromichi;Kita, Yasuyuki. And the article was included in Tetrahedron in 2009.Formula: C6H5NS This article mentions the following:

Bithiophenes and bipyrroles are prepared regioselectively by oxidative coupling reactions of thiophenes and pyrroles mediated by hypervalent iodine reagents such as PhI(O₂CCF₃)₂ (PIFA) in the presence of Lewis acids. Substituted thiophenes and thiophenecarbonitriles, pyrrolecarbonitriles, and indolecarbonitriles are prepared by oxidative substitution reactions of thiophenes, N-tosylpyrroles, and N-tosylindoles with PIFA in the presence of boron trifluoride etherate and nucleophiles such as trimethylsilyl cyanide. (thienyl)aryliodonium salts are prepared by reaction of 3-methylthiophene with either PIFA or with iodosobenzene and acids or by reactions of (hydroxy)aryliodonium tosylates with thiophenes in 2,2,2-trifluoroethanol. All of the above reactions are proposed to occur via single-electron oxidation of the substrates with hypervalent iodine reagents. The paper is preceded by a review of the work of the Kita research group on oxidative cyclizations and intramol. oxidative coupling reactions of arenes mediated by hypervalent iodine reagents. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Formula: C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Formula: C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Site-selectivity in the cyanation of 3-substituted pyridine 1-oxides with trimethylsilanecarbonitrile was written by Sakamoto, Takao;Kaneda, Sohichi;Nishimura, Sumiko;Yamanaka, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Quality Control of 4-methoxypicolinonitrile This article mentions the following:

Treatment of pyridine 1-oxides I (R = Br, Cl, F, OMe, NMe₂, Me, Et, Ph, CONEt₂, CO₂Et, cyano) with Me₃SiCN gave 2- and 6-cyanopyridines II and III. The II – III ratio was strongly influenced by R, with II being the only product when R = F, OMe, NMe₂. Nitropyridine 1-oxides underwent deoxygenation but not cyanation with Me₃SiCN. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Quality Control of 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.Quality Control of 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new synthesis of benzo[b]thiophenes and benzo[c]thiophenes by annulation of disubstituted thiophenes was written by Terpstra, Jan W.;Van Leusen, Albert M.. And the article was included in Journal of Organic Chemistry in 1986.Computed Properties of C6H5NS This article mentions the following:

Nine newly prepared ortho-disubstituted thiophenes I (R = CHO, CO₂Me, cyano; n = 1, 2) and II (R = CO₂Me, cyano, n = 1, 2) react with Michael acceptors to form benzo[b]-, e.g. III, and benzo[c]thiophenes, e.g. IV. This novel annulation process is specifically suited to form benzothiophenes with substituents in the benzene moiety. Substitution patterns so obtained are uncommon and difficultly accessible otherwise; none of the 31 benzothiophenes described in this paper were reported previously. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Computed Properties of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Computed Properties of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A transient outward potassium current activator recapitulates the electrocardiographic manifestations of Brugada syndrome was written by Calloe, Kirstine;Cordeiro, Jonathan M.;Di Diego, Jose M.;Hansen, Rie S.;Grunnet, Morten;Olesen, Soren Peter;Antzelevitch, Charles. And the article was included in Cardiovascular Research in 2009.Computed Properties of C7H4Br2N2 This article mentions the following:

Aims: Transient outward potassium current (I_to) is thought to be central to the pathogenesis of the Brugada syndrome (BrS). However, an I_to activator has not been available with which to validate this hypothesis. Here, we provide a direct test of the hypothesis using a novel I_to activator, NS 5806 (I). Methods and results: Isolated canine ventricular myocytes and coronary-perfused wedge preparations were used. Whole-cell patch-clamp studies showed that I (10 μM) increased peak I_to at +40 mV by 79 ± 4% (24.5 ± 2.2 to 43.6 ± 3.4 pA/pF, n = 7) and slowed the time constant of inactivation from 12.6 ± 3.2 to 20.3 ± 2.9 ms (n = 7). The total charge carried by I_to increased by 186% (from 363.9 ± 40.0 to 1042.0 ± 103.5 pA·ms/pF, n = 7). In ventricular wedge preparations, I increased phase 1 and notch amplitude of the action potential in the epicardium, but not in the endocardium, and accentuated the ECG J-wave, leading to the development of phase 2 re-entry and polymorphic ventricular tachycardia (n = 9). Although sodium and calcium channel blockers are capable of inducing BrS only in right ventricular (RV) wedge preparations, the I_to activator was able to induce the phenotype in wedges from both ventricles. I induced BrS in 4/6 right and 2/10 left ventricular wedge preparations Conclusion: The I_to activator I recapitulates the electrog. and arrhythmic manifestation of BrS, providing evidence in support of its pivotal role in the genesis of the disease. Our findings also suggest that a genetic defect leading to a gain of function of I_to could explain variants of BrS, in which ST-segment elevation or J-waves are evident in both right and left ECG leads. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Computed Properties of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Computed Properties of C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Emission characteristics of new laser dyes for the green and red spectral regions was written by Krymova, A. I.;Petukhov, V. A.;Popov, M. B.. And the article was included in Kvantovaya Elektronika (Moscow) in 1985.SDS of cas: 51473-74-6 This article mentions the following:

Emission characteristics were studies of solutions of certain new dyes from the classes of coumarins, naphthalimides, and benzanthrones under transverse pumping by the ruby laser 2nd-harmonic radiation. Most of the compounds showed laser action in the blue, green, and red spectral regions. A comparison was made of these substances with laser dyes widely used in the given spectral intervals. Compounds were found the lasing efficiency of which exceeds substantially that of uranin in the green region and that of Cresyl Violet in the red region and which are not inferior to them by photostability. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6SDS of cas: 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. 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. SDS of cas: 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of Tertiary Amines from Tris(2-cyanoethyl)amine Using Three Successive Cobalt-Catalyzed Electrophilic Aminations with Organozinc Halides was written by Grassl, Simon;Knochel, Paul. And the article was included in Organic Letters in 2020.Category: nitriles-buliding-blocks This article mentions the following:

A stepwise preparation of triple alkylated or arylated tertiary amines, starting from com. available tris(2-cyanoethyl)amine using three successive reaction sequences involving a selective oxidation (formation of an N-oxide followed by a Cope elimination) leading to an intermediate hydroxylamine, a benzoylation, and a cobalt-catalyzed electrophilic amination with organozinc halides is reported. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Category: nitriles-buliding-blocks).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115â€?25 ppm whereas in isonitriles the shifts are around 155â€?65 ppm. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Immobilized Iron Metal-Containing Ionic Liquid-Catalyzed Chemoselective Transfer Hydrogenation of Nitroarenes into Anilines was written by Patil, Nilesh M.;Sasaki, Takehiko;Bhanage, Bhalchandra M.. And the article was included in ACS Sustainable Chemistry & Engineering in 2016.Computed Properties of C8H8N2 This article mentions the following:

The chemoselective transfer hydrogenation of nitroarenes into anilines was investigated using immobilized iron metal containing ionic liquid (ImmFe-IL) as a versatile heterogeneous catalyst. The present protocol has high atom efficiency with excellent chemoselectivity and regioselectivity. Selective reduction of the nitro group was observed in the presence of other reducing functional groups such as nitrile, ketone, acid, amide, ester, halogens, hydroxyl, olefin, and heterocycles. The developed protocol is also highly selective toward conversion of dinitroarenes into nitroanilines. The present catalytic system uses environmentally benign ethylene glycol as a solvent which is inexpensive, easily available, nontoxic, nonvolatile, nonflammable, thermally stable, and biodegradable. The catalyst was reused up to four consecutive cycles with high activity and selectivity. The fresh catalyst and recycle catalyst was well characterized by XPS anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Computed Properties of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios was written by Peng, Xinhua;Fukui, Naoyuki;Mizuta, Masayuki;Suzuki, Hitomi. And the article was included in Organic & Biomolecular Chemistry in 2003.SDS of cas: 64113-86-6 This article mentions the following:

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and mol. oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodol. based on nitric and sulfuric acids. In some cases, the minor isomer became favored to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6SDS of cas: 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. 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.SDS of cas: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts