Category: nitriles-buliding-blocks

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes was written by Chen, Hao;Mondal, Arup;Wedi, Philipp;van Gemmeren, Manuel. And the article was included in ACS Catalysis in 2019.Reference of 154532-34-0 This article mentions the following:

Aromatic nitriles are key structural units in organic chem. and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting com. available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Reference of 154532-34-0).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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. 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.Reference of 154532-34-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric Synthesis of the Antiarrhythmia Agent d-Sotalol was written by Brodfuehrer, Paul R.;Smith, Patrick;Dillon, John L.;Vemishetti, Purushotham. And the article was included in Organic Process Research & Development in 1997.HPLC of Formula: 101219-69-6 This article mentions the following:

A chiral synthesis of d-Sotalol (I) was developed starting from com. available 4′-(chloroacetyl)methanesulfonanilide. Key step was the asym. reduction of the ketone by BH₃-THF in the presence of a chiral borane. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6HPLC of Formula: 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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: 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solubility measurement and modelling of ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate in four groups mixed solvents was written by Li, Xinbao;Han, Shuo;Zhao, Hongkun. And the article was included in Journal of Chemical Thermodynamics in 2016.Synthetic Route of C12H14N2O4S This article mentions the following:

The solubility of Et 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate (ACET) in binary (acetone + methanol), (acetone + ethanol), (acetone + 1-butanol) and (acetone + isopropanol) solvent mixtures was investigated by the isothermal dissolution equilibrium method under 101.3 kPa. This study was carried out at different mass fractions of acetone ranging from 0.1 to 0.9 at T = (273.15-318.15) K. For the nine groups with each solvent mixture studied, the solubility of ACET in the mixed solutions increased with increasing temperature and mass fraction acetone. At the same temperature and mass fraction of acetone, the solubility of ACET was greater in (acetone + methanol) than in the other three solvent mixtures The exptl. solubility values were correlated by three co-solvency models (Jouyban-Acree model, van’t Hoff-Jouyban-Acree model and Apelblat- Jouyban-Acree model). The relative average deviations (RAD) and the root-mean-square deviations (RMSD) were all less than 1.49 × 10^-2 and 8.99 × 10^-4, resp. The Apelblat-Jouyban-Acree model provided best representation of the exptl. solubility Furthermore, the standard molar enthalpy of the ACET during the dissolving process (Δ_solH^o) was also derived in this work, and the results showed that the dissolution process is endothermic. The exptl. solubility and the models used in this work would be helpful in purifying of ACET from its crude mixtures In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Synthetic Route of C12H14N2O4S).

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. 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 C12H14N2O4S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric transfer hydrogenation of ketones promoted by manganese(I) pre-catalysts supported by bidentate aminophosphines was written by Azouzi, Karim;Bruneau-Voisine, Antoine;Vendier, Laure;Sortais, Jean-Baptiste;Bastin, Stephanie. And the article was included in Catalysis Communications in 2020.Formula: C9H9NO This article mentions the following:

A series of com. available chiral amino-phosphines, in combination with Mn(CO)₅Br, was evaluated for the asym. reduction of ketones to secondary alcs. RCH(OH)R¹ [R = c-hexyl, Ph, 1-naphthyl, etc.; R¹ = Me, Et, i-Pr, etc.] using isopropanol as hydrogen source. With the most selective ligand, the corresponding manganese complex was synthesized and fully characterized. A series of ketones was hydrogenated in the presence of 0.5 mol% of the manganese pre-catalyst affording the chiral alcs. in high yields with enantiomeric excesses up to 99%. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Enantioselective Reduction of Ketones Induced by a C₂-Symmetrical Chiral Hydroxyamide/Titanium(IV) Complex was written by Phothongkam, Supannee;Uang, Biing-Jiun. And the article was included in Asian Journal of Organic Chemistry in 2015.Safety of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

An efficient catalytic system based on the use of a chiral titanium complex generated in situ for the enantioselective reduction of ketones as acetophenone, 1-tetralone, etc. using catecholborane as a reducing agent was developed. The reaction employed the chiral β-hydroxyamide ligand, which can be easily prepared from inexpensive and com. available starting materials, in combination with titanium tetraisopropoxide to achieve enantioenriched secondary alcs. such as (R)-1-tetralol, (R)-1-(2-thienyl)ethanol, etc. in good yields and with up to >99% ee. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Safety of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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 (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Covalently Interlocked Cyclohexa-m-phenylenes and Their Assembly: En Route to Supramolecular 3D Carbon Nanostructures was written by Dumslaff, Bastian;Reuss, Anna N.;Wagner, Manfred;Feng, Xinliang;Narita, Akimitsu;Fytas, George;Muellen, Klaus. And the article was included in Angewandte Chemie, International Edition in 2017.Application In Synthesis of 3-(tert-Butyl)benzonitrile This article mentions the following:

In our search to cluster as many phenylene units as possible in a given space, we have proceeded to the three-dimensional world of benzene-based mols. by employing covalently interlocked cyclohexa-m-phenylenes, as present in the unique paddlewheel-shaped polyphenylene 10. A precursor was conceived, in which freely rotating m-chlorophenylene units provide sufficient solubility along with the necessary proximity for the final ring closure to give 10. Monitoring the assembly of solubilized tert-Bu derivatives of 10 into supramol. carbon nanostructures by dynamic light scattering (DLS) and Brillouin light scattering (BLS) revealed the dimensions of the initially formed aggregates as well as the amorphous character of the solid state. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Application In Synthesis of 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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. 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.Application In Synthesis of 3-(tert-Butyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel palladium-catalyzed amination of aryl halides with amines using rac-P-Phos as the ligand was written by Chen, Huansheng;Wang, Quanrui;Tao, Fenggang. And the article was included in Chinese Journal of Chemistry in 2009.Related Products of 10282-32-3 This article mentions the following:

An efficient palladium-catalyzed amination of aryl halides with amines, using rac-P-Phos as the ancillary ligand and Pd(OAc)₂ as the palladium source is developed. The ligand and all of the synthetic intermediates are stable to air and moisture, allowing easy handling. Aromatic amines, e.g. R¹C₆H₄NR²R³ (R¹ = H, 4-MeO, 4-Ph, etc.; R² = H, Me; R³ = PhCH₂, 4-MeC₆H₄, Ph; R²R³ = N-morpholinyl, N-indolyl), were obtained in high yields. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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. Related Products of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Steric effects in the phototransposition reactions of dialkylbenzenes was written by Gonzalez, C. M.;Pincock, J. A.. And the article was included in Canadian Journal of Chemistry in 2006.Related Products of 29809-13-0 This article mentions the following:

The photochem., photophys. properties, and temperature dependence (-25 to +65 °) of fluorescence by quantum yields and excited singlet state lifetimes in acetonitrile have been examined for three sets of dialkylbenzene derivatives: Set 1 – ortho-xylene (10), tetralin (11), and indan (12); Set 2 – 2,3-dimethylbenzonitrile (9-23), 5-cyanotetralin (T-23), and 4-cyanoindan (I-23); and Set 3 – 3,4-dimethylbenzonitrile (9-34), 6-cyanotetralin (T-34), and 5-cyanoindan (I-34). Phototransposition reactions occur for 10, 9-23, 9-34, and T-34. Fitting of the temperature-dependent fluorescence data to an Arrhenius expression gave A and E_a values for all substrates studied except I-23 and I-34. The fluorescence intensity of these two compounds was essentially independent of temperature For the other compounds, the data revealed that the activation barrier separating the excited singlet state (S₁) from the reactive intermediate, a prefulvene biradical, was the important one in determining the reaction efficiency. The dominant mode of decay of the reactive intermediate was internal return to the starting material. Moreover, the general observation was made that nitrile substitution ortho to one of the alkyl groups in these dialkylbenzene derivatives reduced the rate at which they were converted to the reactive intermediate and, therefore, also the efficiency of the phototransposition reactions. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0Related Products of 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Related Products of 29809-13-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of a Phosphoinositide 3-Kinase (PI3K) β/δ Inhibitor for the Treatment of Phosphatase and Tensin Homolog (PTEN) Deficient Tumors: Building PI3Kβ Potency in a PI3Kδ-Selective Template by Targeting Nonconserved Asp856 was written by Perreault, Stephane;Chandrasekhar, Jayaraman;Cui, Zhi-Hua;Evarts, Jerry;Hao, Jia;Kaplan, Joshua A.;Kashishian, Adam;Keegan, Kathleen S.;Kenney, Thomas;Koditek, David;Lad, Latesh;Lepist, Eve-Irene;McGrath, Mary E.;Patel, Leena;Phillips, Bart;Therrien, Joseph;Treiberg, Jennifer;Yahiaoui, Anella;Phillips, Gary. And the article was included in Journal of Medicinal Chemistry in 2017.Synthetic Route of C5H2Cl2N4 This article mentions the following:

Phosphoinositide 3-kinase (PI3K) beta signaling is required to sustain cancer cell growth in which the tumor suppressor phosphatase and tensin homolog (PTEN) has been deactivated. This manuscript describes the discovery, optimization, and in vivo evaluation of a novel series of PI3Kbeta/delta inhibitors in which PI3Kbeta potency was built in a PI3Kdelta-selective template. This work led to the discovery of a highly selective PI3Kbeta/delta inhibitor displaying excellent pharmacokinetic profile and efficacy in a human PTEN-deficient LNCaP prostate carcinoma xenograft tumor model. In the experiment, the researchers used many compounds, for example, 2-Amino-4,6-dichloropyrimidine-5-carbonitrile (cas: 1277179-33-5Synthetic Route of C5H2Cl2N4).

2-Amino-4,6-dichloropyrimidine-5-carbonitrile (cas: 1277179-33-5) 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. 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.Synthetic Route of C5H2Cl2N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterocyclic studies. Part XXXIX. Ring cleavage of some pyrimidine derivatives in alkali was written by Clark, Jim;Parvizi, Bahman;Colman, Robert. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1976.Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile This article mentions the following:

4-(Substituted amino)-6-chloropyrimidines bearing a mesomeric electron-withdrawing substituent such as NO2, CN, CHO, or Ac at position 5 were cleaved by dilute NaOH at room temperature to give tetra-substituted alkenes. Thus I (0.01 mol. equivalent), H2O (20-30ml), and 2N NaOH (10ml), together with EtOH to aid partial dissolution, were stirred at ∼25° for 18-72 hr to give 98% H2NC(NHCH2Ph):C(CHO)CN. Unlike acid-catalyzed attacks on similar pyrimidines, the course of these basic reactions was not strongly influenced by steric interference between 4(6)- and 5-substituents. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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.Application In Synthesis of 4-Amino-6-chloropyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts