Category: nitriles-buliding-blocks

Second-order nonlinear optical properties of new organic conjugated molecules was written by Kawabe, Y.;Ikeda, H.;Sakai, T.;Kawasaki, K.. And the article was included in Journal of Materials Chemistry in 1992.Computed Properties of C18H10N2 This article mentions the following:

Both real and imaginary parts of the second-order nonlinear optical coefficients for a wide range of new organic conjugated materials were measured. The technique of elec.-field-induced second-harmonic generation to determine the optical nonlinearity is described for materials highly absorptive at the harmonic wavelength. The authors evaluated the mol. nonlinear optical coefficients of nitro compounds and aldehydes, barbituric acid derivatives, fulvene derivatives, chalcone derivatives, retinal derivatives, Schiff base compounds, and fused-ring mols., at 1.064 μm. Among these materials, nitro mols. and Schiff base compounds had large optical nonlinearities and good transparency at visible wavelengths. Barbituric acid derivatives and retinal derivatives also had large nonlinearities, but displayed strong absorption of the harmonics. A large enhancement of nonlinearities was achieved in fulvene derivatives by extending the conjugated chains. S atoms, non-benzoic conjugated systems, and fused rings contributed to nonlinear optical effects. Several mols. had very large second-order optical nonlinearities; the products of the mol. nonlinearities and permanent dipole moments μ₀β of these were of the order of 10^-45-10^-44 esu. The relations between mol. nonlinearity and absorption peak energy are discussed. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of Quinazolinoquinazolinones via a Cascade Approach was written by Ramanathan, Mani;Liu, Shiuh-Tzung. And the article was included in Journal of Organic Chemistry in 2018.Safety of 2-Amino-3-chlorobenzonitrile This article mentions the following:

A one-pot synthesis of quinazolino[3,4-a]quinazolin-13-ones was realized from the direct reaction of o-(methoxycarbonyl)benzenediazonium salts, nitriles, and 2-cyanoanilines in moderate to good yields. This method utilizes the in situ generation of reactive N-arylnitrilium ion, which undergoes further amination/tandem cyclization/amidation to deliver the desired polycyclic scaffolds with consecutive formation of four N-C bonds. Flexibility in substitution patterns, mild reaction conditions, and operational simplicity are the salient features of this methodol. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Safety of 2-Amino-3-chlorobenzonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Acid anilides. XII. Preparation of 4- and 5-hydroxyalkananilides from γ- and δ-lactones was written by de Jonge, A. P.;van der Ven, B.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1965.HPLC of Formula: 4714-63-0 This article mentions the following:

The synthesis of a series of RCH(OH)(CH₂)_nCONHPh (I) (n = 2 or 3) from less than 10 mg. of the corresponding lactones is described. EtBr (1.5 cc.) in 15 cc. dry Et₂O added dropwise to 480 mg. Mg and 5 cc. dry Et₂O at such a rate as to maintain refluxing and diluted with Et₂O to 25 cc., a 1-cc. portion added dropwise to 1 cc. solution of 77 mg. PhNH₂/cc. C₆H₆, and the mixture treated with not more than 10 mg. lactone in dry Et₂O, refluxed 1.5 hrs. under an air condenser until the Et₂O had evaporated, and treated with 10 cc. Et₂O and 2 cc. 3N HCl gave the corresponding I. In this manner were prepared the following I (n = 2) (R and m.p. given): Bu, 114.9-15.8° (Et₂O-petr. ether); iso-Bu, 137.6-8.9° (Et₂O-petr. ether); Am (II), 99.5-100° (Et₂O-petr. ether); C₆H₁₃ (III), 105.2-5.9° (50% EtOH); C₇H₁₅, 106-7° (Et₂O-petr. ether); C₈H₁₇, 108.6-9.6° (50% EtOH). Similarly were prepared the following I (n = 3) (same data given): Pr (IV), 100.9-1.4° (Et₂O-petr. ether); iso-Pr, 92.1-3.2° (Et₂O-petr. ether); Bu, 102.2-3.3° (Et₂O-petr. ether); Am (V), 101.3-1.9° (Et₂O-petr. ether); iso-Am, 102.7-3.8° (Et₂O-petr. ether); C₆H₁₃, 96.4-7.6° (Et₂O); C₇H₁₅ (VI), 104.4-5.3° (Et₂O-petr. ether); C₈H₁₇, 98.0-9.1° (Et₂O); C₉H₁₉, 100.6-1.4° (Et₂O-petr. ether); C₁₀H₂₄, 103.3-4.1° (Et₂O). The rates of the hydrolysis of II, III, IV, and V in 3N HCl were measured spectrophotometrically at 241 mμ; about 8.5 mg. appropriate I in 50 cc. 30% aqueous MeOH was treated with 7 cc. 3.25N HCl; the rate constants k min.^-1 and the half-life period in min. were for the following compounds: II, 0.0271, 25.6; III, 0.0292, 23.7; IV, 0.0189, 36.6; V, 0.0184, 37.7. The solubility of V in cyclohexane at 20° was 43.6 mg./l., that of VI 40.2 mg./l. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0HPLC of Formula: 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. 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.HPLC of Formula: 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Highly Active Palladium Catalyst for Intermolecular Hydroamination. Factors that Control Reactivity and Additions of Functionalized Anilines to Dienes and Vinylarenes was written by Johns, Adam M.;Utsunomiya, Masaru;Incarvito, Christopher D.;Hartwig, John F.. And the article was included in Journal of the American Chemical Society in 2006.COA of Formula: C14H12N2 This article mentions the following:

We report a catalyst for intermol. hydroamination of vinylarenes that is substantially more active for this process than catalysts published previously. With this more reactive catalyst, we demonstrate that additions of amines to vinylarenes and dienes occur in the presence of potentially reactive functional groups, such as ketones with enolizable hydrogens, free alcs., free carboxylic acids, free amides, nitriles, and esters. The catalyst for these reactions is generated from [Pd(η³-allyl)Cl]₂ (with or without added AgOTf) or [Pd(CH₃CN)₄](BF₄)₂ and Xantphos (9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene), which generates complexes with large P-Pd-P bite angles. Studies on the rate of the C-N bond-forming step that occurs by attack of amine on an η³-phenethyl and an η³-allyl complex were conducted to determine the effect of the bite angle on the rate of this nucleophilic attack. Studies on model η³-benzyl complexes containing various bisphosphines showed that the nucleophilic attack was faster for complexes containing larger P-Pd-P bite angles. Studies of substituted unsym. and unsubstituted sym. model η³-allyl complexes showed that nucleophilic attack on complexes ligated by Xantphos was faster than on complexes bearing ligands with smaller bite angles and that nucleophilic attack on unsym. allyl complexes with larger bite angle ligands was faster than on unsym. allyl complexes with smaller bite angle ligands. However, monitoring of catalytic reactions of dienes by ³¹P NMR spectroscopy showed that the concentration of active catalyst was the major factor that controlled rates for reactions of sym. dienes catalyzed by complexes of phosphines with smaller bite angles. The identity of the counterion also affected the rate of attack:reactions of allylpalladium complexes with chloride counterion occurred faster than reactions of allylpalladium complexes with triflate or tetrafluoroborate counterion. As is often observed, the dynamics of the allyl and benzyl complexes also depended on the identity of the counterion. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3COA of Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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. COA of Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Regiocontrolled Remote C-H Olefination of Small Heterocycles was written by Achar, Tapas Kumar;Ramakrishna, Kankanala;Pal, Tapas;Porey, Sandip;Dolui, Pravas;Biswas, Jyoti Prasad;Maiti, Debabrata. And the article was included in Chemistry – A European Journal in 2018.Related Products of 60979-25-1 This article mentions the following:

Achieving site-selective C-H functionalization of arene is a fundamental challenge, as it is mainly controlled by the electronic nature of the mols. A chelation-assisted C-H functionalization strategy overcomes the selectivity issues by utilizing distance and geometry of covalently attached directing groups (DGs). This strategy requires stoichiometric DG installation/removal and a suitable functional group on which to tether the DG. Such strategies are ineffective for small heterocycles unless suitable functional groups are added. Moreover, heterocycles are not the judicious choice as substrates owing to the possibilities of catalyst deactivation. Inspired by recent developments, this work demonstrates the utilization of a chelating template backbone bearing covalently attached directing groups, which enables site-selective remote C-H functionalization of heterocycles. The observed selectivity is the outcome of non-covalent interactions between the heterocycles and bifunctional template backbone. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Related Products of 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. 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.Related Products of 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Covalent-assembly based fluorescent probes for detection of hNQO1 and imaging in living cells was written by Han, Jialing;Cheng, Longhao;Zhu, Ya;Xu, Xiaowei;Ge, Chaoliang. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2020.Computed Properties of C14H14N2O2 This article mentions the following:

Human NAD(P)H: quinone oxidoreductase (hNQO1) is an important biomarker for human malignant tumors. Detection of NQO1 accurately is of great significance to improve the early diagnosis of cancer and prognosis of cancer patients. In this study, based on the covalent assembly strategy, hNQO1-activated fluorescent probes 1 and 2 are constructed by introducing coumarin precursor 2-cyano-3-(4-(diethylamino)-2-hydroxyphenyl) acrylic acid and self-immolative linkers. Under reaction with hNQO1 and NADH, turn-on fluorescence appears due to in-situ formation of the organic fluorescent compound 7-diethylamino-3-cyanocoumarin, and fluorescent intensity changes significantly. Probe 1 and 2 for detection of hNQO1 are not interfered by other substances and have low toxicity in cells. In addition to quant. detection of hNQO1 in vitro, they have also been successfully applied to fluorescent imaging in living cells. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Computed Properties 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).Computed Properties of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitration of 2-cyanothiophene was written by Reynaud, Pierre;Delaby, Raymond. And the article was included in Bulletin de la Societe Chimique de France in 1955.Recommanded Product: 42137-24-6 This article mentions the following:

Fuming HNO₃ (d. 1.49) added dropwise to 2-cyanothiophene in cold Ac₂O (10-12°) gives 80% 4-nitro-2-cyanothiophene (I), m. 102° after recrystallization; 5-nitro-2-cyanothiophene (II), m. 45°, also forms in 20% yield. The reaction is kept easily under control by keeping the temperature below 20° with an ice-salt bath, and the isolation of the isomers presents no difficulty. I refluxed 2 h. with concentrated HCl forms 4-nitro-2-thiophenecarboxylic acid (III), m. 154°, after recrystallization I dissolves easily in HCl, and III crystallizes on cooling. This method also offers a simple method of preparation of 3-nitrothiophene, which is obtained in 77% yield from III by decarboxylation with Cu and quinoline in a tube in a metal bath; CO₂ is evolved at 160°. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Recommanded Product: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Recommanded Product: 42137-24-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reductive cyanation of organic chlorides using CO₂ and NH₃ via Triphos-Ni(I) species was written by Dong, Yanan;Yang, Peiju;Zhao, Shizhen;Li, Yuehui. And the article was included in Nature Communications in 2020.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The reductive cyanation of organic chlorides RCl (R = C₆H₅, naphthalen-1-yl, cyclohexyl, etc.) using CO₂/NH₃ as the electrophilic CN source has been described. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products RCN in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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).Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical Benzylic C-H Functionalization with Isocyanides was written by Tang, Shanyu;Guillot, Regis;Grimaud, Laurence;Vitale, Maxime R.;Vincent, Guillaume. And the article was included in Organic Letters in 2022.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

Author report the challenging direct carbamoylation or cyanation of benzylic C(sp³)-H bonds with an isocyanide via an electrochem. process giving rise to structures which are encountered in several biol. relevant compounds and drugs. This transformation proceeds in mild conditions without the need of any external oxidant and avoids the necessity to start from a prefunctionalized benzylic substrate or the deployment of the cation pool method. Anodic oxidation of the benzylic position and subsequent addition of the isocyanide leads to the formation of a C-C bond and to a nitrilium cation which hydrolysis yields alpha-aryl acetamide derivatives, while elimination of a t-Bu cation delivers alpha-aryl acetonitrile derivatives In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Uses of 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile in the synthesis of heterocyclic compounds with anticonvulsant, behavioral and CNS antidepressant activities was written by El-Sharkawy, K. A.;El-Sayed, N. N. E.;Zaki, M. Y.. And the article was included in International Research Journal of Pure and Applied Chemistry in 2012.COA of Formula: C8H8N2S This article mentions the following:

A reaction of the cyclopenta[b]thiophene with Ph isothiocyanate gave a thiourea derivative The synthesis of the target compounds was achieved using 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile as a starting material. The latter was treated with the active methylene compounds to provide pyrimidine derivatives N-acylation reaction was achieved using acetic anhydride as a reactant. N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thien-2-yl)acetamide was used as a reactant for the synthesis of several derivatives thereof. Finally treatment of N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thien-2-yl)acetamide with different activated nitrile derivatives, hydrazine derivatives gave thienopyridine derivatives and thienopyrimidine derivatives The newly synthesized compounds were tested for anticonvulsant, behavioral and CNS antidepressant activities. The title compounds thus formed included a thienopyrimidine hydrazine imine (I). In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts