60710-80-7 Archives - Nitriles-buliding-blocks

Yeung, Pui Yee et al. published their research in Tetrahedron Letters in 2011 | CAS: 60710-80-7

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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. Formula: C8H8N2

Efficient cyanation of aryl bromides with K₄[Fe(CN)₆] catalyzed by a palladium-indolylphosphine complex was written by Yeung, Pui Yee;Tsang, Chun Pui;Kwong, Fuk Yee. And the article was included in Tetrahedron Letters in 2011.Formula: C8H8N2 This article mentions the following:

This study describes a general palladium-catalyzed cyanation of aryl bromides using K₄[Fe(CN)₆] as the cyanide surrogate. The reactions can be successfully conducted under mild reaction conditions (at 50鎺矯) in mixed solvents (water/MeCN = 1:1) without any surfactant additives, and afford the desired aryl nitriles in good-to-excellent yields. Particularly noteworthy is that this system allows the mildest reaction temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K₄[Fe(CN)₆] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing -PCy₂ moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding ligands with -PPh₂ group. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Formula: C8H8N2).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Song, Pinrao et al. published their research in Bioorganic & Medicinal Chemistry in 2015 | CAS: 60710-80-7

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?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 锜? bond in the triple bond. 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.Recommanded Product: 3-Amino-4-methylbenzonitrile

Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold was written by Song, Pinrao;Chen, Ming;Ma, Xiaodong;Xu, Lei;Liu, Tao;Zhou, Yubo;Hu, Yongzhou. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Recommanded Product: 3-Amino-4-methylbenzonitrile This article mentions the following:

A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biol. evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC₅₀ values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC₅₀ values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, resp. Afterwards, for exploring the mol. target, compounds2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3灏? BRAF, IKK灏?and PKC. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Recommanded Product: 3-Amino-4-methylbenzonitrile).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mix, Hermann et al. published their research in Chemische Berichte in 1956 | CAS: 60710-80-7

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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.Synthetic Route of C8H8N2

Organic catalysts. XL. Synthetic dehydrogenases. 8 was written by Mix, Hermann;Krause, Hans Walter. And the article was included in Chemische Berichte in 1956.Synthetic Route of C8H8N2 This article mentions the following:

Some isatins, CMe:CH.CH:CR.C:C.NH.CO.CO (I), and N-(7-methylisatin-4-carbonyl)amino acid Et esters (II), substituted in the 4-position, are prepared and tested for their dehydrogenase activity. Treating p-MeC₆H₄CO₂H with fuming HNO₃ yields 4,3-Me(O₂N)C₆H₃CO₂H, m. 188-9°, which, reduced with Raney Ni in dioxane at 120° and 100 atm., gives 90% 4,3-Me(H₂N)C₆H₃CO₂H (III), m. 162°. Heating 5 g. III in 150 cc. H₂O containing 2 cc. concentrated H₂SO₄ with 5.5 g. CCl₃CHO.H₂O (IV) and 6.5 g. (HONH₂)₂.H₂SO₄ (V) yields 3-isonitrosoacetamido-4-methylbenzoic acid which (10 g.), heated in 22 cc. concentrated H₂SO₄ at 85-90° and kept 0.5 hr. at 95-100°, gives 72% I (R = CO₂H) (VI), yellow-red needles, m. 278-80°; Et ester, prepared by heating 5 g. VI in 150 cc. EtOH-HCl 0.5 hr. on a water bath and chromatographing over Al₂O₃, orange rods, m. 205°. Heating 5 g. 4,3-Me(H₂N)C₆H₃CN, m. 81°, 6.3 g. IV, and 7.5 g. V in 430 cc. H₂O and 3 cc. concentrated H₂SO₄ gives 2-2.5 g. isonitroso compound which, heated with concentrated H₂SO₄, yields I (R = CONH₂), brick-red crystals, decompose above 270°. Adding 0.94 cc. ClCO₂Et dropwise to a solution of 2 g. VI and 2.28 g. Bu₃N in 20 cc. CHCl₃ at -5°, stirring the mixture 0.5 hr. at -5°, then adding 900 mg. PhNH₂, and stirring the mixture 12 hrs. give I (R = CONHPh), small red rods, m. 308°; I (R = CONEt₂), light red leaflets, m. 192°. The following II are prepared (amino acid given): alanine, light red rods, m. 254°; norvaline, light red leaflets, m. 220°; α-aminobutyric acid, red leaflets, m. 218-19°; glutamic di-Et ester, red needles, m. 171-2°; glutamic mono-Et ester, long red needles, m. 186-7°; phenylalanine, red needles, m. 225-6°; tryptophan Me ester, purple crystals, m. 254°. Treating 1.2 g. 2,4-Me₂C₆H₃NH₂ in 30 cc. H₂O and 1.16 g. concentrated H₂SO₄ with 1.7 g. IV and 1.9 g. V yields isonitrosoacetamido-p-xylene which, added to 10 cc. concentrated H₂SO₄ at 65-7° and the mixture heated 20 min. at 65-70°, gives 4,7-dimethylisatin, yellow-red precipitate, m. 261°. Reduction of 4,3-Me(O₂N)C₆H₃NHAc with Raney Ni at 120° and 100 atm. gives 100% 3,4-Me(H₂N)C₆H₃NHAc, m. 159°, which (6 g.), stirred 4-5 hrs. at 36-40° with 6 g. IV and 7.2 g. V, yields 3-isonitrosoacetamido-4-methylacetanilide. Heating the latter 45 min. in 10 cc. concentrated H₂SO₄ at 95-100° gives 4-amino-7-methylisatin, light red needles, charring above 310°. The dehydrogenase activity of these compounds has been tested by measuring the time required to decolorize a solution of 2 × 10^-5 moles methylene blue and 2.25 × 10^-4 moles DL-alanine in 71% HCONMe₂ at 40°. The results, given in a table, show that V is the most active catalyst. The introduction of the Me group at the 7-position has no effect on the dehydrogenation velocity. For the calculation of the partial velocities of the catalysis the P_S curves of some of the compounds are given. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Synthetic Route of C8H8N2).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cumming, John G. et al. published their research in Journal of Medicinal Chemistry in 2015 | CAS: 60710-80-7

Discovery and Characterization of MAPK-activated Protein Kinase-2 Prevention of Activation Inhibitors was written by Cumming, John G.;Debreczeni, Judit E.;Edfeldt, Fredrik;Evertsson, Emma;Harrison, Martin;Holdgate, Geoffrey A.;James, Michael J.;Lamont, Scott G.;Oldham, Keith;Sullivan, Jane E.;Wells, Stuart L.. And the article was included in Journal of Medicinal Chemistry in 2015.Quality Control of 3-Amino-4-methylbenzonitrile This article mentions the following:

Two structurally distinct series of novel, MAPK-activated kinase-2 prevention of activation inhibitors have been discovered by high throughput screening. Preliminary structure-activity relationship (SAR) studies revealed substructural features that influence the selective inhibition of the activation by p38α of the downstream kinase MK2 in preference to an alternative substrate, MSK1. Enzyme kinetics, surface plasmon resonance (SPR), 2D protein NMR, and x-ray crystallog. were used to determine the binding mode and the mol. mechanism of action. The compounds bind competitively to the ATP binding site of p38α but unexpectedly with higher affinity in the p38α-MK2 complex compared with p38α alone. This observation is hypothesized to be the origin of the substrate selectivity. The two lead series identified are suitable for further investigation for their potential to treat chronic inflammatory diseases with improved tolerability over previously studied p38α inhibitors. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Quality Control of 3-Amino-4-methylbenzonitrile).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Le et al. published their research in Journal of Medicinal Chemistry in 2004 | CAS: 60710-80-7

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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: C8H8N2

Design, Synthesis, and Biological Activity of 4-[(4-Cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles as Potent and Selective Farnesyltransferase(FTase) Inhibitors was written by Wang, Le;Wang, Gary T.;Wang, Xilu;Tong, Yunsong;Sullivan, Gerry;Park, David;Leonard, Nicholas M.;Li, Qun;Cohen, Jerry;Gu, Wen-Zhen;Zhang, Haiying;Bauch, Joy L.;Jakob, Clarissa G.;Hutchins, Charles W.;Stoll, Vincent S.;Marsh, Kennan;Rosenberg, Saul H.;Sham, Hing L.;Lin, Nan-Horng. And the article was included in Journal of Medicinal Chemistry in 2004.Formula: C8H8N2 This article mentions the following:

A novel series of 4-[(4-cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles have been synthesized as selective farnesyltransferase inhibitors using a structure-based design. X-ray cocrystal structures of compound 6-[[(1R)-(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-3′-methoxy[1,1′-biphenyl]-3-carbonitrile-FTase-HFP and A313326-FTase-HFP confirmed our initial design. The decreased interaction between the aryl groups and Ser 48 in GGTase-I binding site could be one possible reason to explain the improved selectivity for this new series of FTase inhibitors. Medicinal chem. efforts led to the discovery of 3-cyano-6-[[(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-N-phenylbenzamide (I) with potent cellular activity (EC₅₀ = 3.5 nM) and outstanding pharmacokinetic profiles in dog (96% bioavailable, 18.4 h oral t_1/2, and 0.19 L/(h·kg) plasma clearance). In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Formula: C8H8N2).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9/8/21 News Sources of common compounds: 60710-80-7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60710-80-7, its application will become more common.

Some common heterocyclic compound, 60710-80-7, name is 3-Amino-4-methylbenzonitrile, molecular formula is C8H8N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C8H8N2

i 2-Chloro-N-(5-cyano-2-methylphenyl)acetamide The subtitle compound was prepared from 5-cyano-2-methylaniline (1.6 g) and chloroacetyl chloride (1.1 ml) by the method of Example 33 step (iii) as a white solid. Yield: 1.85 g MS: APCI (-ve) 207 (M-1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60710-80-7, its application will become more common.

Reference:
Patent; Meghani, Premji; Bennion, Colin; US2003/13721; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of C8H8N2

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 60710-80-7, name is 3-Amino-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-4-methylbenzonitrile

General procedure: NaNO2 aqueous solution (13.80g, 0.2mol, 32.20mL) was added dropwise to a mixture of 3a (21.40g, 0.2mol), H2O (190mL), and 12N HCl aqueous solution (50mL, 0.6mol) at 0C. The mixture was stirred at 0C for 30min and then was filtered. The precooled NaBF4 (24.20g, 0.22mol) dissolved in H2O (90mL) was added to the filtrate and kept stirring at 0C for an additional 40min. The precipitate was collected by filtration, washed with cold ethanol (50mL×3), cold ethylether (50mL×3), and concentrated in vacuo to deliver diazonium salt (19.19g) as a yellow solid. To a solution of diazonium salt (19.19g, 0.093mol) in CHCl3 (231mL), KOAc (15.15g, 0.155mol) was added. The mixture was stirred at room temperature for 4h. Afterwards, the reaction was quenched with water (200mL) and extracted with CH2Cl2 (70mL×3). The organic phase was washed with brine (50mL×3), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The obtained crude residue was purified by recrystallization to give the title compound 7.51g.

Reference:
Article; Song, Pinrao; Chen, Ming; Ma, Xiaodong; Xu, Lei; Liu, Tao; Zhou, Yubo; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1858 – 1868;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Extended knowledge of C8H8N2

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 60710-80-7, name is 3-Amino-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

(Boc)20 (50 g, 227 mmol) was added portion-wise to a stirred solution of 3-amino-4- methylbenzonitrile (7) (10 g, 75.7 mmol) and DMAP (0.5 g) in THF (250 ml_). After 30 minutes, the reaction was heated at 60 C overnight. The crude reaction mixture was purified over silica gel to obtain a white solid tert-butyl 5-cyano-2-methylphenylcarbamate (34) (17.5 g, quantitative yield). MS m/z 233.1 (M+1 )+. NH2OH (20 ml_, 50% in water) was added to a stirred solution of tert-butyl 5-cyano-2- methylphenylcarbamate (34) (17.5 g, 75.3 mmol) in EtOH (200 ml_) and the resulting solution was heated at 50 C for 10 hours. The solvent was then evaporated and the product was titurated with EtOAc and hexane to obtain a white solid (Z)-tert-butyl 5-(N’- hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) in a quantitative yield which was used without further purification. MS m/z 266.1 (M+1 )+.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New learning discoveries about 60710-80-7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-methylbenzonitrile, its application will become more common.

Related Products of 60710-80-7,Some common heterocyclic compound, 60710-80-7, name is 3-Amino-4-methylbenzonitrile, molecular formula is C8H8N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of intermediate 7R (231 g, 0.556 mol) in 1,4-dioxane (2.3 L), ptoluenesulfonic acid monohydrate (179 g, 0.95 mol) and 3-amino-4-methylbenzonitrile (110 g, 0.83 mol) were added, purged three times with N2 and stirred at 95 C for 12 h. Then, the reaction mixture was cooled down to 20 C, and a solution of NaHCO3 was added to neutralize the mixture. The precipitated solid formed was filtrated andcombined with another precipitate coming from a reaction performed on 179 g of intermediate 7R. The resulting solid was dissolved in Me-THF (5 L), washed with water three times (3 x 5 L). A silanethiol resin [from Shanghai Meryer CO.,LTD] (60 g) was added to the mixture and reflux for 1.5 h. Then, the resulting mixture was filtered through a pad of celite and concentrated under vacuum. The residue wassuspended in EtOH (5L) overnight, filtered and dissolved in THF (3L). Methyl ten?butylether (6 L) was added to THF and the solid was precipitated, filtered and dried to afford 243g of compound 1.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New learning discoveries about 60710-80-7

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

60710-80-7, name is 3-Amino-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

DIPEA (1 mL; 5.8 mmol) was added to a solution of 3-amino-4-methylbenzonitrile(661 mg; 5 mmol) and 2,4-dichloro-1,3,5-triazine (750 mg; 5 mmol) in ACN (30 mL).The reaction mixture was stirred overnight at room temperature. The solvent wasremoved by evaporation and the residue was partionned between water and EtOAc. The organic layer was decanted, washed with water, then brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH; mobile phase: gradient from 0% EtOAc, 100% petroleum ether to 50% EtOAc, 50% petroleum ether). The fractions containing the product were collectedand evaporated to dryness yielding 700 mg (57%) of intermediate 543.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.