Author: Jessica.F

La-Mg mixed oxide as a highly basic water resistant catalyst for utilization of CO₂ in the synthesis of quinazoline-2,4(1H,3H)-dione was written by Rasal, Kalidas B.;Yadav, Ganapati D.. And the article was included in RSC Advances in 2016.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

The synthesis of quinazoline-2,4(1H,3H)-dione was done by direct utilization of CO₂ in the cyclization of 2-aminobenzonitrile (2-ABN) using lanthanum magnesium mixed oxide (La-Mg MO) as a strong basic catalyst under mild reaction conditions in water. It gave a conversion of~92% with 100% selectivity at 140 °C in 14 h. La-Mg MO was prepared by hydrothermal method using urea as homogeneous precipitating agent. The catalyst was characterized by different anal. techniques like BET, XRD, FT-IR, scanning electron microscope, and TGA, and the basicity by CO₂-TPD and acidity by NH₃ TPD. Various reaction parameters were studied to predict the reaction mechanism and kinetics. The reaction follows the Langmuir-Hinshelwood-Hougen-Watson (LHHW) type kinetics model with an apparent activation energy of 23.3 kcal mol^-1. The catalyst was recycled three times with an insignificant change in activity. The overall process is clean and green. 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. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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 In Synthesis of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant was written by Xu, Hailiang;Zhao, Chenglong;Qian, Qun;Deng, Wei;Gong, Hegui. And the article was included in Chemical Science in 2013.Recommanded Product: 4-methoxypicolinonitrile This article mentions the following:

(Pinacolato)diboron was used as the terminal reductant which allowed the efficient Ni-catalyzed coupling of unactivated secondary and primary alkyl halides, generating the C(sp³)-C(sp³) coupling products in good yields. The mild catalytic conditions displayed an excellent functional group tolerance and good chemoselectivities which required only 1.5 equivalent of primary bromides for the coupling with secondary bromides. Mechanistic studies suggest that an in-situ organoborane/Suzuki process was not likely and was proved that the base and ligand had more profound impact on selecting this reductive coupling pathway. The good chemoselectivity appears to be evoked by the formation of Ni-Bpin catalytic intermediates which demands matched sizes and reactivities of the alkyl halide coupling partners for optimal coupling efficiency. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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.Recommanded Product: 4-methoxypicolinonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of N-substituted amidines was written by Cooper, F. C.;Partridge, M. W.. And the article was included in Journal of the Chemical Society in 1953.Application of 5203-15-6 This article mentions the following:

PhNH₂ (I) (10.1 g.), 25.4 g. 4-MeC₆H₄CN (II), 5 g. powd. Na, and 100 cc. PhMe-free C₆H₆ (III) refluxed 3 days and worked up as described by Lottermoser [J. prakt. Chem. 54, 113(1896)] gave 95% 4-MeC₆H₄C(:NH)NHPh (IV) (analyses indicated 88% CN^– and 75% PhMe based on the equation: 2 RCN + ArNH₂ + 2 Na â†?RC(:NAr)NH^– Na⁺ + RH + NaCN). I (20.2 g.), 25.4. g. II, 5 g. powd. Na, and 100 mL. III as in the previous example gave 96% IV and 0.5% kyanphenin (V). I (9.3 g.), 3.9 g. finely powd. NaNH₂ and 100 cc. C₆H₆ refluxed about 1.25 h., 10.3 g. PhCN (VI) added, and the whole refluxed 2.25 h. gave 12.6 g. PhC(:NH)NHPh (VII), m. 114-15°; with granular NaNH₂, the yield of VII was 57%, and with PhNMe₂ as solvent, 23%. I (9.3 g.), 2.3 g. Na, 10.3 g. VI, and 100 cc. dry C₆H₆ refluxed 27 h. evolved no permanent gas; the products were VII, PhCH₂NH₂ (VIII) (identified as benzylammonium picrate), and BzH; I and Na in boiling C₆H₆ gave about 2% PhNHNa; VII and Na in boiling C₆H₆ gave no permanent gas and small amounts of VIII and I; I and VI refluxed 8 h. gave a trace of PhC(:NPh)NHPh. Two procedures were used to prepare the following compounds in procedure A, 0.1 mol each of powd. Na, the amine, and the nitrile in 100 cc. dry C₆H₆ were refluxed 20-30 h., 15 cc. EtOH was added, the base extracted into aqueous MeCH(OH)CO₂H, isolated by addition of aqueous NH₃, and crystallized from petr. ether; in Procedure B, granular NaNH₂ was used in place of the Na of Procedure A (R, R’ in RC(:NH)NHR’, procedure, % yield, m. p., and m.p. of picrate): 4-MeC₆H₄, Ph, A, 65, 151-2°, 152-3°; 4-MeOC₆H₄, Ph, A, 51, 147-8°, 129-30°; 4-ClC₆H₄, Ph, A, 64, 140-1°, 175-6°; 4-sec-BuOC₆H₄, Ph, A, 63, 116.0-16.5°, 138-40°; Ph, 2-MeC₆H₄, A, 61, 109-10°, 152-3°; Ph, 4-MeOC₆H₄, A, 73, 115.5-16.5°, 171-3°; Ph, 2-C₁₀H₇, A, 39 (Procedure B gave 54%), 128.5-9.5°, 216.5-18.0°; Ph, 2-C₅H₄N, A, 65, 98.5-9.5°, 206-7°; Ph, cyclohexyl, A, 43, 115-16°, 142-3°; 2-MeC₆H₄, Ph, B, 47 122-3°, 175-6°; 4-PhOC₆H₄, Ph, A, 83, 183.5-4.5°, 145-6°; Ph, 2-thiazolyl, B, 6, 90-1°, 162-3°; PhCH₂, Ph, B, 64, 140-1°, 109-10°; Me, Ph, B, 36, -, 190-1°; 2-phenylbenzimidazole, B, 72, 299-301°, 275-6° (decomposition). The following were prepared incidental to the above: p-ClC₆H₄NHCPh:NH.HCl.2H₂O, needles, m. 103-6° (decomposition) (from H₂O) {base, m. 114-15° [acetate, needles, m. 131-2° (from C₆H₆); picrate, m. 180-1°]}; N-(2-hydroxyethyl)benzamidinium picrate, prisms, m. 140-2°, solidifies and remelts at 180-215° (decomposition); 4-sec-BuOC₆H₄CN, b_1.3 109-11°, n²⁰_D 1.5256; 4-HOC₆H₄(NHPh):NH.HO₃SPh, m. 180-2°, (picrate, m. 82-4° (from aqueous iso-PrOH), base, small needles, m. 182.5-3.0°). In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Application of 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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.Application of 5203-15-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly enantioselective bioreduction of prochiral ketones by stem and germinated plant of Brassica oleracea variety italica was written by Mohammadi, Mehdi;Yousefi, Maryam;Habibi, Zohreh. And the article was included in Biocatalysis and Biotransformation in 2011.Category: nitriles-buliding-blocks This article mentions the following:

An eco-friendly and environmentally benign asym. reduction of a broad range of prochiral ketones employing Brassica oleracea variety italica (stems and germinated plant) as a novel biocatalyst was developed. It was found that B. oleracea variety italica could be used effectively for enantioselective bioreduction in aqueous medium with moderate to excellent chem. yield and enantiomeric excess (ee). This process is more efficient and generates less waste than conventional chem. reagents or microorganisms. Both R- and S-configurations were obtained by these asym. reactions. The best ee were achieved for pyridine derivatives (92-99%). The ee in germinated plant reactions were significantly higher than those of stem reactions. The low cost and the easy availability of these biocatalysts suggest their possible use for large scale preparations of important chiral alcs. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Category: nitriles-buliding-blocks).

(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. 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

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Nitrile – Wikipedia,
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Rational Design, Synthesis, and Characterization of Deep Blue Phosphorescent Ir(III) Complexes Containing (4′-Substituted-2′-pyridyl)-1,2,4-triazole Ancillary Ligands was written by Park, Hea Jung;Kim, Ji Na;Yoo, Hyun-Ji;Wee, Kyung-Ryang;Kang, Sang Ook;Cho, Dae Won;Yoon, Ung Chan. And the article was included in Journal of Organic Chemistry in 2013.SDS of cas: 36057-44-0 This article mentions the following:

On the basis of the results of frontier orbital considerations, 4-substituted-2′-pyridyltriazoles were designed to serve as ancillary ligands in 2-phenylpyridine main ligand containing heteroleptic iridium(III) complexes that display deep blue phosphorescence emission. The iridium(III) complexes, Ir1–Ir7, prepared using the new ancillary ligands, were found to display structured, highly quantum efficient (Φ_p = 0.20-0.42) phosphorescence with emission maxima in the blue to deep blue 448-456 nm at room temperature In accord with predictions based on frontier orbital considerations, the complexes were observed to have emission properties that are dependent on the electronic nature of substituents at the C-4 position of the pyridine moiety of the ancillary ligand. Importantly, placement of an electron-donating Me group at C-4′ of the pyridine ring of the 5-(pyridine-2′-yl)-3-trifluoromethyl-1,2,4-triazole ancillary ligand leads to an iridium(III) complex that displays a deep blue phosphorescence emission maximum at 448 nm in both the liquid and film states at room temperature Finally, an OLED device, constructed using an Ir-complex containing the optimized ancillary ligand as the dopant, was found to emit deep blue color with a CIE of 0.15, 0.18, which is close to the perfect goal of 0.15, 0.15. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0SDS of cas: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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: 36057-44-0

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Nitrile – Wikipedia,
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Ketimines. III. ω-Cyclohexylalkyl alkyl type was written by Pickard, P. L.;Young, C. W.. And the article was included in Journal of the American Chemical Society in 1951.Product Details of 4435-14-7 This article mentions the following:

In this abstract, R = cyclohexyl throughout.) Acid chlorides, R(CH₂)_XCl (read x, yield (%), b.p., d₄²³, n_D²⁰): 3, 92.5, b₁ 83°, 1.0175, 1.4710; 5, 96, b₁ 106°, 0.9987, 1.4714. Slow addition of the acid chlorides to NH₄OH at 0° and crystallization of the precipitate from MeOH-H₂O gave above 80% of the amides, R(CH₂)₃CONH₂: × = 3, m. 111°; 5, m. 117°. Dehydration with excess POCl₃ gave the nitriles, R(CH₂)_xCN (read x, yield (%), b.p., d₄²⁰, n_D²⁰): 1, 70, b₁ 57°. 0.9180, 1.4575; 2, 80, b₁ 71°, 0.9107, 1.4602; 3, 83, b₁ 82°, 0.9056, 1.4607; 4, 85, b₁ 93°, 0.8950, 1.4618; 5, 86, b₁ 112°, 0.9879, 1.4637. The ketimines, R(CH₂)_x C(:NH)CHMeEt were prepared from 0.25 mole MeEtCHBr and 0.20 mole nitrile by the method of Pickard and Vaughan (C.A. 45,381 1a) (read x, yield (%), b.p., d₄²⁰, and n_D²⁰): 2, 56, b₂ 101°, 0.8680, 1.4689; 3, 43, b₁ 107°, 0.8611, 1.4699; 4, 45, b₁ 121°, 0.8754, 1.4700; 5, 60, b₁ 130°, 0.8808, 1.4719. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Product Details of 4435-14-7).

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. 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.Product Details of 4435-14-7

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Nitrile – Wikipedia,
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Non-covalent thrombin inhibitors featuring P₃-heterocycles with P₁-monocyclic arginine surrogates was written by Reiner, John E.;Siev, Daniel V.;Araldi, Gian-Luca;Cui, Jingrong Jean;Ho, Jonathan Z.;Reddy, Komandla Malla;Mamedova, Lala;Vu, Phong H.;Lee, Kuen-Shan S.;Minami, Nathaniel K.;Gibson, Tony S.;Anderson, Susanne M.;Bradbury, Annette E.;Nolan, Thomas G.;Semple, J. Edward. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.COA of Formula: C5H4N4 This article mentions the following:

Investigations on P₂-P₃-heterocyclic dipeptide surrogates directed towards identification of an orally bioavailable thrombin inhibitor led us to pursue novel classes of achiral, non-covalent P₁-arginine derivatives The design, synthesis, and biol. activity of inhibitors NC1-NC30 that feature three classes of monocyclic P₁-arginine surrogates will be disclosed: (1) (hetero)aromatic amidines, amines and hydroxyamidines, (2) 2-aminopyrazines, and (3) 2-aminopyrimidines and 2-aminotetrahydropyrimidines. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6COA of Formula: C5H4N4).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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.COA of Formula: C5H4N4

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β-Amino alcohols as ligands for asymmetric transfer hydrogenation of ketones in water was written by Wu, Xiaofeng;Li, Xiaohong;McConville, Matthew;Saidi, Ourida;Xiao, Jianliang. And the article was included in Journal of Molecular Catalysis A: Chemical in 2006.HPLC of Formula: 101219-69-6 This article mentions the following:

Chiral β-amino alcs. were used as ligands for ruthenium, rhodium and iridium-catalyzed asym. transfer hydrogenation of acetophenone derivatives in water with formate as reductant. The catalysts were shown to be capable of asym. transfer hydrogenation of ketones in water, but their activities and enantioselectivity varied with the ligands used and with solution pH values, with higher pH favoring higher rates and better enantioselectivity. 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 101219-69-6

Referemce:
Nitrile – Wikipedia,
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Cobalt(II)/TPPMS-Catalyzed Dehydrative Nucleophilic Substitution of Alcohols in Water was written by Hikawa, Hidemasa;Ijichi, Yukiko;Kikkawa, Shoko;Azumaya, Isao. And the article was included in European Journal of Organic Chemistry in 2017.Computed Properties of C8H5F3N2 This article mentions the following:

A green and sustainable direct dehydrative amination of alcs., catalyzed by cobalt(II)/TPPMS (sodium diphenylphosphinobenzene-3-sulfonate) in water, is described. Earth-abundant cobalt was used as Co(hfac)₂·xH₂O (hfac: hexafluoroacetylacetone), which acts as a highly efficient Lewis acidic catalyst. This simple atom-economical protocol features mild conditions without the need for a base or other additives and affords the corresponding benzylic and allylic anilines along with water as the only coproduct. Mechanistic studies suggest that this system is driven by direct nucleophilic substitution of alcs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Computed Properties of C8H5F3N2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO₂ and deacetalization-Knoevenagel condensation was written by Lv, Hongxiao;Fan, Liming;Chen, Hongtai;Zhang, Xiutang;Gao, Yanpeng. And the article was included in Dalton Transactions in 2022.Application of 55490-87-4 This article mentions the following:

The rare combination of Ba(II) (5s) and Zn^II (3d) in the presence of the structure-oriented TDP⁶– ligand generated the nanochannel-based hybrid material {[(CH₃)₂NH₂]₂[BaZn(TDP)(H₂O)]·DMF·5H₂O}_n (NUC-51, H₆TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochem. characteristics such as nanoscopic channels, high porosity, large sp. surface area and high heat/water-resistance. This is the first 3D [Ba^IIZn^II(CO₂)₆(H₂O)]-based nano-porous host framework, whose activated state NUC-51a possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn²⁺ ions, 7-coordinated Ba²⁺ ions, uncoordinated carboxyl oxygen atoms and N_pyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO₂ at 55°C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70°C. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts