Category: 4488-22-6

4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 17-iodo-5alpha-androsta-16-ene 1 (0.5 mmol), 2,2′-diamino-1,1′-binaphthalene 2 (varied from 1.0 mmol to 0.125 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (3 20 mL), 5% hydrochloric acid (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to give a solid material. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200 mm), EtOAc/CHCl3 or hexane/CHCl3 (the exact ratios are specified in Section 4.4 for each compound). 4.3. Characterisation of the products (Fig. 3) (Sax)-3: Yield: 410 mg (72%). Off-white yellow solid, mp 137-142 C; [Found: C, 84.55; H, 7.65; N, 4.70; C40H44N2O requires C,84.46; H, 7.80; N, 4.93]; Rf (5% EtOAc/CHCl3) 0.68. 1H NMR (CDCl3) delta: 8.94 (1H, d, 9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.94 (1H, d,8.2 Hz, H-50), 7.87 (1H, d, 8.5 Hz, H-300), 7.82 (1H, d, 7.5 Hz, H-400), 7.43 (1H, dt, 6.3 Hz, 1.6 Hz, H-60), 7.35 (1H, s, NH), 7.31 (1H, dt,8.5 Hz, 0.8 Hz, H-70), 7.29-7.26 (2H, m, H-600 , H-600), 7.23 (1H, dt,6.8 Hz, 1.1 Hz, H-700), 7.16 (1H, d, 8.7 Hz, H-80), 6.96 (1H, d, 8.2 Hz,H-800), 6.21 (1H, dd, 2.9 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.7 Hz, 6.5 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd,16.7 Hz, 11.9 Hz, 1.4 Hz, 15-CHaHb), 1.07-0.54 (23H, m, skeleton protons), 0.78 (3H, s, 19-CH3), 0.62 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.6, 150.4, 143.0, 140.0, 135.7, 133.8, 132.5. 131.1, 130.3, 129.3, 128.3, 128.2, 128.1, 127.5, 126.8, 125.3, 124.9, 123.6, 122.8, 120.4, 119.7, 118.1, 110.5, 56.8, 54.7, 47.2, 45.3, 38.4, 36.3, 34.2, 33.7, 31.8, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 16.0, 12.1. IR (KBr, m(cm1)): 3440 (amide-NH), 3398 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (relint.): 551.4 (29), 285.2 (100). [alpha]D20 = 37.1 (c 1.34, CHCl3). (Rax)-3: Yield: 114 mg (20%). Off-white solid substance; [Found:C, 84.30; H, 7.66; N, 4.77; C40H44N2O requires C, 84.46; H, 7.80; N,4.93]; Rf (5% EtOAc/CHCl3) 0.72. 1H NMR (CDCl3) delta: 8.95 (1H, d,9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.93 (1H, d, 7.9 Hz, H-50), 7.87 (1H, d, 8.9 Hz, H-300), 7.82 (1H, d, 7.8 Hz, H-400), 7.43 (1H, dt,6.4 Hz, 1.2 Hz, H-60), 7.36 (1H, s, NH), 7.31 (1H, dt, 8.6 Hz, 0.8 Hz,H-70), 7.29-7.26 (2H, m, H-6”, H”), 7.23 (1H, dt, 6.9 Hz, 1.5 Hz,H-7”), 7.16 (1H, d, 8.5 Hz, H-8′), 6.96 (1H, d, 8.4 Hz, H-8”), 6.21 (1H, dd, 3.1 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.3 Hz, 6.4 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd, 16.6 Hz,11.7 Hz, 2.0 Hz, 15-CHaHb), 1.07-0.53 (23H, m, skeleton protons), 0.77 (3H, s, 19-CH3), 0.31 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.5, 150.4, 143.1, 140.2, 135.7, 133.8, 132.4, 131.1, 130.3, 129.3, 128.4, 128.3, 128.2, 127.5, 126.8, 125.3, 124.9, 123.6,122.8, 120.4, 119.7, 118.0, 110.6, 56.8, 54.8, 47.2, 45.2, 38.4, 36.3, 34.2, 33.7, 31.7, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 15.5, 12.1. IR(KBr, m (cm1)): 3441 (amide-NH), 3396 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (rel int.): 551.4 (29), 285.2 (100). [alpha]D20 = +191.5 (c 0.914, CHCl3). (Sax)-4: Yield: 102 mg (12%). Beige solid substance; [Found: C,84.31; H, 8.35; N, 3.12; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.69. 1H NMR (CDCl3) alpha: 8.94 (2H, d,9.2 Hz, H-3′), 8.08 (2H, d, 9.2 Hz, H-4′), 7.95 (2H, d, 8.2 Hz, H-5′),7.46 (2H, dt, 7.2 Hz, 0.9 Hz, H-6′), 7.35 (2H, dt, 7.2 Hz, 0.9 Hz, H-7′), 7.1 (2H, d, 9.3 Hz, H-8′), 7.13 (2H, s, NH), 6.05 (2H, dd, 3.1 Hz, 1.5 Hz, H-16), 2.02 (2H, ddd, 16.8 Hz, 6.4 Hz, 3.1 Hz, 15-CHaHb), 1.88 (2H, dd, 9.9 Hz, 3.1 Hz, 14-CH), 1.75 (2H, ddd, 16.8 Hz,11.7 Hz, 1.5 Hz, 15-CHaHb), 1.69-0.54 (44H, m, skeleton protons), 0.77 (6H, s, 19-CH3), 0.57 (6H, s, 18-CH3). 13C NMR (CDCl3) alpha: 163.6, 150.2, 140.0, 136.0, 135.2, 132.4, 131.3, 130.0, 128.2,127.5, 125.3, 124.9, 120.5, 118.1, 56.6, 54.8, 47.2, 45.4, 38.4, 36.3, 34.2, 33.6, 31.7, 31.4, 29.0, 28.8, 26.8, 22.1, 20.5, 16.1, 12.1. IR (KBr, m (cm1)): 3408 (amide-NH), 1677 (CON), 1621 (CC). MS m/z (rel int.): 853.6 ((M+H)+); 875.6 ((M+Na)+), 891.5 ((M+K)+). [alpha]D20 = +12.0 (c 0.418, CHCl3). (Rax)-4: Yield: 85 mg (10%). Beige solid substance; [Found: C,84.28; H, 8.30; N, 3.06; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.74. 1H NMR (CDCl3) alpha: 8.95 (2H, d,9.0 Hz, H-3′), 8.08 (2H, d, 9.0 Hz, H-4′), 7.96 (2H, d, 7.8 Hz, H-5′), 7.46 (2H, dt, 7.8 Hz, 0.9 Hz, H-6’…, 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Mikle, Gbor; Boros, Borbla; Kollr, Lszl; Tetrahedron Asymmetry; vol. 25; 23; (2014); p. 1527 – 1531;,
Chiral Catalysts
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4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1) Synthesis of N,N’-di-p-toluenesulfonyl-1,1′-binaphthyl-2,2′-diamine Under nitrogen atmosphere, to a solution in which 1,1′-binaphthyl-2,2′-diamine (0.5 mmol) was dissolved in pyridine (1 mL) was added p-toluenesulfonyl chloride (1.1 mmol) at room temperature, and the mixture was reacted for 5 to 12 hours with stirring. After completion of the reaction, the resulting red suspension was diluted with ethyl acetate, and back-extracted with 1N hydrochloric acid to remove pyridine. The resulting organic layer was dried with sodium sulfate to remove the solvent, and the residue was purified by column chromatography to obtain an objective substance as a pale yellow to white solid in more than 95% yield.

4488-22-6, Big data shows that 4488-22-6 is playing an increasingly important role.

Reference£º
Patent; Terada, Masahiro; Uraguchi, Daisuke; Sorimachi, Keiichi; Shimizu, Hideo; US2007/142639; (2007); A1;,
Chiral Catalysts
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.

Under nitrogen conditions, add tris (dibenzylidene-base acetone) dipalladium (37 mg, 0.04 mmol, purchased from ANEG) to Schlenk bottles with magnetons, 1,1′-Binaphthyl-2,2′-bisdiphenylphosphine (50 mg, 0.08 mmol, purchased from Anagi), cesium carbonate (3.65 g, 11.2 mmol, purchased from Anagi), 2-trifluoromethanesulfonyl cycloheptatrienone (4.88 g, 19.2 mmol), 1,1′-bi-2-naphthylamine (2.27 g, 8 mmol, purchased from Enagi) and 50 ml of toluene. The resulting mixture was stirred at 100 C for 24 hours. The reaction was completed and the temperature was reduced to room temperature. After the toluene-insoluble solid was filtered off with diatomaceous earth, 100 mesh silica gel was added to the resulting solution to spin dry the sample. The obtained crude product was then passed through a 200-300 mesh silica gel column, using ethyl acetate as an eluent, and the eluent was spin-dried to obtain a brown solid (2.68 g, yield 68%)., 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; University of Science and Technology of China; Chen Changle; Zhang Pan; (17 pag.)CN110423246; (2019); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 1 Preparation of (R)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diamine (R-1): 200 mg (R)-1,1′-binaphthyl-2,2′-diamine (purchased from Aldrich Chemical Company), 20 mg PtO2 and 20 mL glacial acetic acid were charged into a 50 mL autoclave equipped with a magnetic stirring bar. The autoclave was closed and 1,000 KPa hydrogen gas was charged. The solution was stirred with a magnetic stirrer for 120 hours at room temperature. After releasing the hydrogen gas and removing the solid catalyst by filtration, the mixture was neutralized with aqueous NaHCO3 solution followed by extraction with 50 mL ethyl acetate three times. The combined extracts were dried with sodium sulfate and the solvent was removed with a rotary evaporator to give 210 mg of crude product (R-1). The crude product was purified by crystallization with 5 mL ethyl acetate and 15 mL hexane to give 180 mg crystals of R-1 (87.5% of theoretical yield)., 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The Hong Kong Polytechnic University; US5919981; (1999); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

The chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diamine,cas is 4488-22-6, mainly used in chemical industry, its synthesis route is as follows.,4488-22-6

Sodium nitrite (1.2g, 18.0mmol) in 3mL of water was added slowly to a stirred solution of BINAM (1.2g, 4.0mmol) and HBF4 (45% in H2O, 10mL) at 0C. Then the reaction was stirred at 0C for 30min and further stirred at room temperature for 30min. The resulting yellow solid was filtered using a Buechner funnel and washed with cold HBF4 (2¡Á5mL), H2O (2¡Á10mL) and EtOH (10mL). The diazonium salt 1 solid (1.8g) was dried under a vacuum desiccator and stored at 0C (yellow solid).

As the rapid development of chemical substances, we look forward to future research findings about 4488-22-6

Reference£º
Article; Ganapathy, Dhandapani; Sekar, Govindasamy; Catalysis Communications; vol. 39; (2013); p. 50 – 54;,
Chiral Catalysts
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4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-1A (28.5 g, 100 mmol) was dissolved in acetonitrile (MeCN), and 10 ml of hydrochloric acid was slowly added thereto, followed by stirring at room temperature for 3 hours. After the reaction was completed by adding water, the resulting solid was filtered, washed with an aqueous solution of potassium carbonate and dried to obtain the compound of Formula 7-1B (25 g, yield 90%).

4488-22-6, The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LG Chemical Co., Ltd.; Sin, Chang Hwan; Kim, Kong Gyeom; Cheon, Min Sung; Kwon, Hyuk Jun; Kim, Dong Heon; (50 pag.)KR101656560; (2016); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.

To a solution of BINAM (100 mg, 0.35 mmol) and pyridine (85 mL, 1.05 mmol) inacetnitrile (3.5 mL) was added p-toluenesulfonylchloride (73 mg, 0.38 mmol), and the mixture was refluxed for 12 h. After cooling to ambient temperature, the reaction was quenched with brine (10 mL) and extracted with EtOAc (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purifiedby column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-2; yield: 119 mg (78%)., 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
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[1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,4488-22-6

Preparation of ligands.; Synthesis of imines.; 3 mmol of bisnaphthyldiamine and 6 mmol of ketone were dissolved in 30 mL of anhydrous toluene. A few mg of para toluene sulfonic acid were added. After addition of 30 g of activated 4 angstroem molecular sieves by 10 g portions, the reaction mixture was stirred at a temperature of 110C for a period of time of 3 days. Molecular sieves were filtered off and the solvent was removed under vacuum. The resulting solid was crystallised from methanol to give the product. Two compounds were obtained and characterised. Bis-naphthyldi(phenylmethyleneimine) was obtained as a yellow solid with a yield of 79 %. [Show Image] The NMR results were as follows. 1H-RMN (300 MHz, CD2Cl2) [Show Image] (ppm) : 6.64 (d, 2H), 6.7-4-78 (m, 8H), 6.93-6.97 (m, 4H), 7.05 (t, 2H), 7.19-7.48 (m, 6H), 7.50 (t, 2H), 7.68 (d, 6H), 7.77 (d, 2H) 13C-RMN (75 MHz, CD2Cl2) [Show Image] (ppm) : 122.2, 124.1, 124.2, 126.1, 126.5, 127.8, 127.9, 128.0, 128.2, 128.3, 128.9, 130.0, 130.2, 130.6, 130.7, 133.9, 136.6, 140.8, 147.6, 167.2

With the rapid development of chemical substances, we look forward to future research findings about 4488-22-6

Reference£º
Patent; TOTAL PETROCHEMICALS RESEARCH FELUY; EP1982975; (2008); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2 (142 mg, 0.5 mmol) in pyridine (1 mL)/DCM (4 mL) was added mesylchloride (126 mg, 1.1 mmol) and the orange mixture was stirred at r.t. After 24 h, a second portion of mesylchloride was added (126 mg, 1.1 mmol) and stirring was continued. After complete conversion (TLC), the reaction was acidified (HCl, 1 M) and sufficiently extracted with DCM. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude mixture was purified by MPLC (EtOAc (30?50%)/heptane) to yield 223 mg (quant.) of 3a as a mixture of tautomers; m.p.: 221-222 C. 1H-NMR (C2-symmetric tautomer) delta = 8.10 (d, J = 8.9 Hz, 2H); 8.02 (d, J = 8.9 Hz, 2H); 7.95 (br.d, J = 8.2 Hz, 2H); 7.47 (ddd, J =8.0, 6.8, 1.1 Hz, 2H); 7.31 (ddd, J = 8.4, 6.9, 1.3 Hz, 2H); 6.99 (br.d, J = 8.3 Hz, 2H); 6.02 (br.s, 2H); 2.97 (s, 6H). 13C-NMR delta = 134.4 (C); 132.5 (C); 131.5 (CH); 131.2 (C); 128.7 (CH); 128.2 (CH); 126.1 (CH); 124.5 (CH); 118.5 (C); 118.2 (CH); 41.0 (CH3). HRMS: calcd for C22H20NaN2O4S2 [M + Na]+: 463.0762; found 463.0762., 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lemmerer, Miran; Abraham, Michael; Brutiu, Bogdan R.; Roller, Alexander; Widhalm, Michael; Molecules; vol. 24; 17; (2019);,
Chiral Catalysts
Chiral catalysts – SlideShare

4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the “dead time” to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.

4488-22-6, As the paragraph descriping shows that 4488-22-6 is playing an increasingly important role.

Reference£º
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; ARMSTRONG, Daniel, W.; PING, Sun; BREITBACH, Zachary, S.; WANG, Chunlei; WO2010/148191; (2010); A2;,
Chiral Catalysts
Chiral catalysts – SlideShare