Category: nitriles-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 67832-11-5, Computed Properties of C8H6BrN

(a) (Ss,R)-2-methyl-propane-2-sulphinic acid-[2-(5-bromo-2-cyano-phenyl)-1 – methyl-ethyl]-amide; 6.0 ml (42.8 mmol) diisopropylamine are dissolved in 80 ml THF, slowly combined with 26.7 ml (42.8 mmol) butyllithium solution (1.6 M in n-hexane) at 00C, stirred for 30 min. Then this solution is cooled to -78C and a solution of 4.0 g (20.4 mmol) 4-bromo-2-methyl-benzonithle in 15 ml THF is slowly added dropwise. This mixture is stirred for 70 minutes at -78C and then a solution of 1.5 g (10.2 mmol) (Ss)-ethylidene-N-tert.-butyl-sulphinamide (prepared analogously to J. Ellman et al. J. Org. Chem. 2001 , 66, 8772 from acetaldehyde and (Ss)-tert.-butylsulphinamide) in 15 ml THF is added dropwise. The mixture is stirred for 2.5 hours at -70 to -65C. The reaction mixture is combined with 5 ml sat. Ammonium chloride solution and after thawing it is combined with water and ethyl acetate. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases are dried on sodium sulphate and evaporated to dryness in vacuo. The residue is purified by column chromatography on silica gel (eluant DCM/MeOH 100:3) Yield: 830 mg (24%) Rt value: 1.45 min (Method B) Mass spectrum: (M+H)+ = 343/345 (bromine isotope)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/135524; (2008); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile

A mixture of compound 1 (0.45 g, 0.41 mmol), AcONH4 (0.13 g,1.65 mmol) and 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile(0.48 g, 2.47 mmol) in chloroform (30 mL) was stirredunder an atmosphere of N2 gas at 80 C overnight. The reactionmixture was then allowed to cool to room temperature. Next,dichloromethane and methanol were poured into the cooledcompound mixture for precipitation. The crude compound wasfiltered and purified by column chromatography on silica gel usingdichloromethane as the eluent to gain pure product SP-IC (2) as a red solid (0.42 g); yield 57.53%. FTIR-ATR (ZnSe, cm-1): 2894, 2220,1697, 1653, 1586, 1540, 1386; 1H NMR (CDCl3, 500 MHz, ppm):delta 8.78 (4H, s), 8.69 (4H, d, J 7.95 Hz), 8.04 (4H, d, J 7.90 Hz), 7.88(4H, d, J 6.75 Hz), 7.78e7.70 (12H, m), 7.67 (4H, s), 7.03 (4H, d,J 1.20 Hz), 2.48 (7H, t, J 7.95 Hz), 1.50-4 (8H, m), 1.19-1.07(25H, m), 0.80 (12H, t, J 7.05 Hz); 13C NMR (CDCl3,125 MHz, ppm):delta 188.18, 168.96, 160.56, 155.07, 147.36, 141.76, 141.51, 139.92, 137.98,136.87, 135.21, 134.60, 133.59, 129.87, 125.38, 124.35, 123.83, 122.86,121.46, 121.28, 114.44, 114.36, 69.90, 31.49, 30.79, 29.70, 29.08,28.70, 22.47, 14.09; UV-Vis (CHCl3) lmax/nm(epsilon/105 mol1 dm3 cm-1): 539 (1.44); Found: C, 78.18; H, 4.90; N,6.22%; molecular formula C117H88N8O4S4 requires C, 78.15; H, 4.93;N, 6.23%; Found: [MH] 1797.5803; molecular formulaC117H88N8O4S4 requires [MH] 1797.5811.

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Park, Seo Yeon; Park, Gi Eun; Choi, Suna; Lee, Ji Hyung; Lee, Dae Hee; Cho, Min Ju; Choi, Dong Hoon; Dyes and Pigments; vol. 146; (2017); p. 226 – 233;,
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Related Products of 61150-58-1, A common heterocyclic compound, 61150-58-1, name is 2-(2-Bromo-4-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, its 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 s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

The synthetic route of 61150-58-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
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Related Products of 17417-09-3,Some common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

a 5-Amino-2-fluorobenzonitrile A mixture of 5-nitro-2-fluorobenzonitrile (10 g, 60.2 mmol), Fe powder (17 g, 0.3 mol), and NH4Cl (1.7 g, 30 mmol) in EtOH/H2O (100 mL, 9:1) was heated at reflux in 2 h. The mixture was filtered at hot. The filtrate was concentrated, taken up in H2O, stirred, filtered air-dried to obtain the title solid as a tan solid, (5.0 g, 71%). 1H NMR (400 MHz, DMSO-d6): d 5.54 (s, 2H), 6.85 (m, 2H), 7.16 (t, J=8.1 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-nitrobenzonitrile, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
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Electric Literature of 50397-74-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 50397-74-5 name is 4-Amino-3-bromobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

An ethanolic solution (5 mL) of 4-amino-3-bromobenzonitrile (L3, 1 mmol, 0.197 g) was added to ethanolicsolution (5 mL) of AgNO3 (0.6 mmol, 0.1 g). The test tube was covered with a perforated foil. Afterkeeping the solution in air for 4 days, light yellow crystals of 3 suitable for structure determinationwere obtained. Yield 80%, m.p. 130-132 C. Anal. Calcd for C21H15AgBr3N7O3: C, 33.15; H, 1.99; N, 12.88%. Found: C, 33.14; H, 1.97; N, 12.89%. IR (KBr, cm-1): 3481 (m), 3360 (s), 3215 (w), 2628 (w), 2221 (s), 1769(w), 1633 (s), 1594 (m), 1507 (s), 1388 (s). 1H NMR (400 MHz, DMSO) delta/ppm: 7.83 (d, J = 1.9 Hz, 1H), 7.45(dd, J = 8.5, 1.9 Hz, 1H), 6.82 (d, J = 8.5 Hz, 1H), 6.37 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Qian, Wei; Yuan, Hao-Kun; Zhang, Ran; Fang, Rui-Qin; Journal of Coordination Chemistry; vol. 69; 23; (2016); p. 3593 – 3602;,
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Application of 98730-77-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30 mmol, 2.36 g) in dichloromethane (30 mL) was treated with triethylamine (48.6 mmol, 6.83 mL, 4.92 g) and portionwise with methanesulfonyl chloride (31.6 mmol, 2.445 mL, 3.62 g) keeping the reaction mixture at 0 C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (*3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (1-cyanocyclopropyl)methyl methanesulfonate (3.77 g). 1H NMR (CDCL3, 400 MHz): delta 1.18 (2H, m), 1.46 (2H, m), 3.14 (3H, s), 4.18 (2H, s)

The chemical industry reduces the impact on the environment during synthesis 1-(Hydroxymethyl)cyclopropanecarbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); A1;,
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Application of 330793-38-9, 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. 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-(Methyoxy)-4-prop-2-en-l-ylbenzonitrile To a 50 mL flask containing a stir bar were added 2-methoxy-4-bromobenzonitrile (0.30 g, 1.4 mmol), palladium tetrakis (82 mg, 0.071 mmol), allyltri-n-butyltin (0.88 mL, 2.8 mmol), and lithium chloride (0.12 g, 2.8 mmol). The resulting mixture was then dissolved in anhydrous toluene (16 mL); the flask was placed in an oil bath and heated at 130 °C. LC as well as TLC (hexanes/EtOAc =1/0.3) indicated that reaction had gone to completion. The flask was taken out of the oil bath and cooled to room temperature. To the flask was added EtOAc (40 mL) and the mixture was transferred into a separatory funnel and washed with brine. The organic phase was dried over Na2S04, filtered and concentrated to dryness. It was then dissolved in DCM and absorbed into silica gel. The slica gel was then loaded onto a silica column for separation with the solvent systems of hexanes/EtOAc (1/0.3) to provide 2-(methyloxy)-4-prop-2-en-l- ylbenzonitrile. LC-MS (IE, m/z): 174 [M + 1]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
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Reference of 2941-29-9, These common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, its 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.

A mixture of 2-cyanocyclopentanone (20.0 g, 183 mmol, prepared as described in Fleming et al, J. Org. Chem. 2007, 72, 1431-1436 in the Supporting Information), water (24.7 ml), and sodium cyanide (14.8 g, 302 mmol) was cooled with an ice bath to a temperature of 5 °C to 10 °C. A mixture of sulfuric acid (29.3 ml, 550 mmol) and water (24.7 ml), said mixture having a temperature of 10 °C, was added drop wise within 0.5 h while stirring. The ice bath was then removed, and the mixture was stirred for 2.5 h at room temperature. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (3 x 100 ml). The combined extracts were dried with magnesium sulfate, and pyridine (51 ml, 631 mmol) was added. The solution was cooled with an ice bath to a temperature of 5 °C to 10 °C, and acetyl chloride (40.0 ml, 561 mmol) was added drop wise. The resulting mixture was stirred at 0 °C for 2 h, and then at room temperature overnight. After filtration and concentration under reduced pressure, toluene (100 ml) and ethyldiisopropylamine (94 ml, 553 mmol) were added to the residue, and the mixture was stirred at 100 °C for 6 h, and at room temperature overnight. The mixture was poured into a mixture of aqueous, concentrated hydrochloric acid (68 ml) and water (70 ml), phases were separated, the aqueous phase was extracted with ethyl acetate (3 x 150 ml), the combined extracts were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to yield 22.5 g of a dark oil. Distillation (2 mbar) yielded 8.6 g (40percent) of compound of formula (II) (bp 66-71 °C). 1H NMR (CDCls, 400 MHz) compound of formula (II): delta 2.17 (quint, J = 7 Hz, 2H), 2.83 (t, J = 7 Hz, 4H).

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONZA LTD; ZARAGOZA DOERWALD, Florencio; WO2013/102634; (2013); A1;,
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Reference of 3288-99-1, These common heterocyclic compound, 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)acetonitrile, its 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.

In a 10 L-reaction flask equipped with a rectification column and a separating tank, 314 g (1.81 mol) of 4-tert-butylphenylacetonitrile, 300 g (1.65 mol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 3000 g of heptane, 225 g of diethylene glycol dimethyl ether, and 99 g of diethylene glycol monoethyl ether were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 381 g (1.98 mol) of 28% sodium methoxide methanol solution was added dropwise over 10 hours, and the resulting mixture was further reacted for 7 hours. After cooling to 30 C. or less, 3000 g of water was added to separate out heptane phase, and the resulting aqueous phase was further washed with 600 g of heptane to separate out heptane phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 466 g (yield 91.5%) of 2-(4-tert-butylphenyl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrile. After adding 2760 g of xylene to the aqueous phase, 206 g (1.98 mol) of 35% hydrochloric acid was added dropwise to be neutralized. After separating out the aqueous phase, the resulting organic phase was washed two times with 600 g of water and the aqueous phase was separated out to obtain xylene solution of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile. A quantitative analysis with liquid chromatography showed that the xylene solution contained 456 g (yield 89.6%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
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Application of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

It was prepared as described for 8. Starting from 2-amino-6-fluorobenzonitrile (318 mg, 2.31 mmol) in 1,2-dichloroethane (25 mL) and enone 7 (R9 = i-Pr) (272 mg, 1.53 mmol) in 1,2-dichloroethane (15 mL), a crude product (383 mg) was obtained and subjected to column chromatography [silica gel (19 g), hexane/AcOEt/25% aqueous NH4OH mixtures as eluent]. On elution with hexane/AcOEt/25% aqueous NH4OH 98:2:0.1, huprine 10 (220 mg, 42% yield) was obtained as a beige solid.A solution of huprine 10 (220 mg, 0.74 mmol) in CH2Cl2 (15 mL) was filtered through a PTFE 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 30:1 (9.3 mL), 10·HCl (138 mg) was obtained as a beige solid, mp >300 C (dec.) (AcOEt/MeOH 30:1). IR (KBr) nu 3500-2500 (max at 3494, 3370, 3312, 3201, 3158, 3024, 2958, 2929, 2891, 2833, 2750, 2669, C-H, N-H, and N+-H st), 1640, 1595, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.87 (d, J = 7.0 Hz, 3H) and 0.89 (d, J = 7.0 Hz, 3 H) [9-CH(CH3)2], 1.97 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.02-2.12 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], superimposed in part 2.08 (br d, J = 17.5 Hz, 1H, 10-Hendo), 2.52 (br dd, J = 17.5 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.80 (m, 1H, 7-H), 2.86 (dm, J ? 18.0 Hz, 1H, 6-Hendo), 3.21 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.41 (m, 1H, 11-H), 4.85 (s, NH2 and NH+), 5.58 (dm, J = 5.0 Hz, 1H, 8-H), 7.34 (ddd, J = 13.5 Hz, J’ = 8.0 Hz, J = 1.0 Hz, 1H, 2-H), 7.56 (br d, J = 8.5 Hz, 1H, 4-H), 7.82 (dddm, J ? J’ ? 8.5 Hz, J = 5.5 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 27.2 (CH, C11), 27.9 (CH, C7), 29.6 (CH2, C13), 31.7 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 36.1 (CH2, C6), 107.2 (C, d, J ? 11.5 Hz, C12a), 112.2 (CH, d, J = 23.3 Hz, C2), 115.7 (C, C11a), 116.3 (CH, C4), 122.2 (CH, C8), 134.9 (CH, d, J ? 11.5 Hz, C3), 140.6 (C, C4a), 144.5 (C, C9), 152.9 (C) and 155.3 (C) (C5a and C12), 161.1 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H21FN2·HCl·3/4H2O (346.36): C, 65.89; H, 6.84; N, 8.09; Cl, 10.24. Found: C, 65.55; H, 6.62; N, 7.99; Cl, 10.21.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
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