Category: chiral-nitrogen-ligands

110-70-3, A common heterocyclic compound, 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.”110-70-3

The ligand BPMEN was synthesized via a previouslyreported procedure (Singh et al. 2017). A solution of potassiumcarbonate (5.1 g, 37 mmol) in 15 mL water was dropwiseadded to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (3 g, 18.3 mmol in 10 mL). Afterabout 30 min of stirring at room temperature, the reactionmixture was extracted with dichloromethane (3 ¡Á 20 mL).The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered, and the solventwas removed under vacuum. The resulted residue was thendissolved in dichloromethane (10 mL). The above solutionwas added dropwise to a solution of N,N?-dimethylethylenediamine(0.942 mL, 8.75 mmol) in dichloromethane(25 mL). After this addition, 20 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixturewas stirred for next 60 h at room temperature. After stirringwas finished, another fraction of sodium hydroxide (20 mL,1 M) was added rapidly. The reaction mixture was extractedwith dichloromethane (3 ¡Á 50 mL) and the combined organicportion was dried over anhydrous sodium sulfate. Evaporationof solvent led to isolation of the ligand BPMEN as adark orange oil. (2.1 g, Yield – 89%) 1H NMR (500 MHz,Methanol-d4) delta 8.45 (d, 2H, pyridine ring), 7.76 (m, 2H, pyridinering), 7.52 (d, 2H, pyridine ring), 7.30 (m, 2H, pyridinering), 3.67 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-),2.26 (s, 6H, N-CH3). ESI-MS+: [BPMEN + H]+ = 271.15 m/z+ (experimental) 271.19 m/z+ (theoretical).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand N1,N2-Dimethylethane-1,2-diamine reaction routes.

Reference£º
Article; Botcha, Niharika Krishna; Gutha, Rithvik R.; Sadeghi, Seyed M.; Mukherjee, Anusree; Photosynthesis Research; vol. 143; 2; (2020); p. 143 – 153;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 110-70-3

The ligand L1 was synthesized via previously reported procedure[23]. A solution of potassium carbonate (2.55 g, 18.45 mmol)in 10 mL water was dropwise added to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (1.5 g, 9.15 mmol in10 mL). After about 30 min. of stirring at room temperature, thereaction mixture was extracted with dichloromethane(3 20 mL). The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered and the solvent wasremoved under vacuum. The resulted residue was then dissolvedin dichloromethane (10 mL). The dichloromethane solution of 2-chloromethyl-pyridine was added dropwise to a solution of N,N0-dimethylethylenediamine (0.471 mL, 5.34 mmol) in dichloromethane(15 mL). After this addition, 10 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixture wasstirred for next 60 h at room temperature. After stirring was finished,another fraction of sodium hydroxide (10 mL, 1 M) wasadded rapidly. The reaction mixture was extracted with dichloromethane(3 25 mL) and combined organic portion was dried overanhydrous sodium sulfate. Evaporation of solvent led to isolationof the ligand L1 as a dark orange oil. (1.13 g, Yield 79%) 1H NMR(500 MHz, Methanol-d4) d 7.27 (m, 2H, pyridine ring), 7.50 (d,2H, pyridine ring), 7.76 (m, 2H, pyridine ring), 8.45 (d, 2H, pyridinering), 3.68 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-), 2.26 (s, 6H,N-CH3). IR (cm1): 2945, 2789, 1589, 1569, 1472, 1432, 1360,1304, 1146, 1090, 1031, 994, 635, 614, 418.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Reference£º
Article; Singh, Nirupama; Niklas, Jens; Poluektov, Oleg; Van Heuvelen, Katherine M.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 455; (2017); p. 221 – 230;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 31886-58-5

(S)-Ugi-amine 1 (2.57 g, 10 mmol) was dissolved in 25 mL of diethyl ether, and n-butyllithium (8 mL, 2.5 mol/L) was added dropwise to the reaction system under nitrogen protection and ice salt bath cooling. After that, the temperature was slowly raised to room temperature, and the reaction was stirred for 3 hours. Under ice cooling, chlorobis(3,5-dimethylphenyl)phosphine (5.53 g, 20 mmol) was added dropwise thereto, and after the completion of the dropwise addition, the mixture was slowly warmed to room temperature, and the reaction was stirred for 24 hours. The reaction was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. Dry over anhydrous sodium sulfate, Concentration and column chromatography gave the product 10 (3.03 g, 61%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Patent; Zhejiang University of Technology; Zhong Weihui; Ling Fei; Nian Sanfei; (14 pag.)CN108774271; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound.

General procedure: To a solution of (R)-Ugi?s amine 3 (2.57 g, 10 mmol) in TBME (20 mL) was added 1.6 M t-BuLi solution in n-hexane (6.8 mL, 10.88 mmol) at 0 C. After the addition was complete, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to 0 C again, and Ar2PCl (11 mmol) was added in one portion. After stirring for 20 min at 0 C, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then quenched by the addition of saturated NaHCO3 solution (20 mL). The organic layer was separated and dried over MgSO4, and the solvent was removed under reduced pressure, after which the filtrate was concentrated. The residue was purified by chromatography to afford 4a, 4e, and 4f.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Article; Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1567 – 1571;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 110-70-3

A solution of di-tert-butyl dicarbonate (4.95 g, 22.69 mmol) in CH2Cl2 (240 mL) was added dropwise to a stirred solution of N,N?-dimethylethane-1,2-diamine (4 g, 45.38 mmol) in CH2Cl2 (80 mL) over a period of 20h. The resulting mixture was stirred at r.t. for 3h. The mixture was then washed sequentially with sat. Na2CO3 (2 x 100 mL), water (50 mL), and sat. brine (50 mL). The organic solution was dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-10% CH3OH in CH2Cl2 gave the title compound (2.177 g, 51%) as a pale yellow oil; 1H NMR: 1.40 (9H, s), 2.28 (3H, s), 2.57 (2H, t), 2.79 (3H, s), 3.20 (2H, t).

110-70-3, 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.,110-70-3 ,N1,N2-Dimethylethane-1,2-diamine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; FINLAY, Maurice, Raymond, Verschoyle; WARD, Richard, Andrew; KADAMBAR, Vasantha, Krishna; CHANDRASHEKAR, Reddy, C.; MURUGAN, Andiappan; REDFEARN, Heather, Marie; WO2013/14448; (2013); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 110-70-3

A solution of N,N?-dimethylethylenediamine (1.72g, 20mmol) in dry tetrahydrofuran (60mL) was treated with 2-chloromethylpyridine hydrochloride (6.604g, 40mmol) and triethylamine (8.093g, 80mmol) and the mixture was stirred under reflux for 18h. The resulting mixture was cooled to in ice and the triethylamine hydrobromide was removed by filtration. The filtrate was then treated with 10mL 15% NaOH solution and extracted with CH2Cl2 (3¡Á40mL). The combined extracts were dried over anhydrous MgSO4. Removal of the solvent with rotary evaporator yielded dark brown oil which was chromatographed on alumina and eluted with 95/5 (v/v) mixture of ethyl acetate/MeOH (Rf=0.81). The purified ligand was obtained as yellow viscous oil (yield: 4.2g, 79%). Selected IR bands (cm-1): nu(C-H) 3064 (w), 2949 (m), 2802 (m); pyridyl groups: 1592 (s), 1577 (m), 1474 (m), 1435 (s). 1H NMR: 8.43 (m, 2H), 7.70 (m, 2H), 7.37 (m, 2H), 7.72 (m, 2H), 3.58 (s, 4H), 2.51 (s, 4H), 2.14 (s, 6H); 13C NMR: 159.74 (2-py), 149.06 (6-py), 136.78 (4-py), 123.01 (3-py), 122.42 (5-py), 63.95 (N-CH2-py), 35.40 (-CH2-CH2-N), 42.94 (CH3-N), 40.60 (CH3-N).

The chemical industry reduces the impact on the environment during synthesis,110-70-3,N1,N2-Dimethylethane-1,2-diamine,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Mautner, Franz A.; Koikawa, Masayuki; Mikuriya, Masahiro; Harrelson, Emily V.; Massoud, Salah S.; Polyhedron; vol. 59; (2013); p. 17 – 22;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Name is Tris[2-(dimethylamino)ethyl]amine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 33527-91-2, its synthesis route is as follows.

LiBEt3H (1 mL, 1.0 M in THF, 1 mmol) and Me6TREN (0.26 mL,1 mmol) were added to 5 mL of hexane, precipitating a white powder.THF was slowly added dropwise with stirring until a homogeneoussolution was obtained (approx. 3 mL) Cooling of the solutionat 30 C yielded X-ray quality colorless crystals (225 mg, 67%).1H NMR (400.1 MHz, C6D6, 300 K): delta 2.06 (s, 18H, Me6TREN Me),1.86 (t, 6H, 3JHH = 4.95 Hz, Me6TREN CH2), 1.78 (t, 6H, 3JHH = 4.95 Hz,Me6TREN CH2), 1.54 (t, 9H, 3JHH = 7.43 Hz, BCH2CH3), 0.95 ppm(q, 6H, 3JHH = 7.43 Hz, BCH2CH3).13C NMR (100.6 MHz, C6D6, 300 K): delta 57.2 (Me6TREN CH2), 50.6(Me6TREN CH2), 45.7 (Me6TREN Me), 16.7 (m, 1JBC = 41.5 Hz,BCH2CH3), 14.2 ppm (BCH2CH3).7Li NMR (155.5 MHz, C6D6, 300 K): delta 0.18 ppm.11B NMR (128.3 MHz, C6D6, 300 K): delta 11.3 ppm (broad singlet).Elemental analysis for C18H46N4LiB: Calc.: C, 64.28; H, 13.79; N,16.66. Found: C, 64.24; H, 13.49; N, 16.75%.

33527-91-2, 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.,33527-91-2 ,Tris[2-(dimethylamino)ethyl]amine, other downstream synthetic routes, hurry up and to see

Reference£º
Article; Kennedy, Alan R.; McLellan, Ross; McNeil, Greg J.; Mulvey, Robert E.; Robertson, Stuart D.; Polyhedron; vol. 103; (2016); p. 94 – 99;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

As a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, name is N1,N2-Dimethylethane-1,2-diamine, and cas is 110-70-3, its synthesis route is as follows.

Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N’-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61%)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Reference£º
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

33527-91-2, A common heterocyclic compound, 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.”33527-91-2

To a solution of tris(2-dimethylaminoethyl)amine (0.403 g, 1.75 mmol) in acetonitrile (4 mL) was added 1-bromohexadecane (1.63 g, 5.35 mmol). The resulting mixture was heated at reflux with stirring for 18 hours, during which time awhite solid was observed. After cooling, and the addition of a cold hexanes/acetone mixture (15 mL, 1:1), to the reaction flask, the precipitate was filtered with a Buchner funnel, and rinsed with a cold hexanes/acetone mixture (2O mL, 1:1), resulting in T-16,16,16 (1.67 g, 84%) as a white powder; mp=229-258 C; ?H NMR (300 MI-Tz, CDC13) oe 4.11-4.02 (m, 6H), 3.64-3.55 (m, 6H), 3.45-3.37 (m, 6H), 3.35(s, 18H), 1.78-1.66 (m, 6H), 1.40-1.18 (m, 78H), 0.88-0.81 (m, 9H); high resolution mass spectrum (ESI) m/z 302.0073 ([Mj3 calculated for [C6oH,29N4j3: 302.0067). ?H spectmm of compound T-16,16,16 can be found in Figure 54.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33527-91-2,Tris[2-(dimethylamino)ethyl]amine,its application will become more common.

Reference£º
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; VILLANOVA UNIVERSITY; WUEST, William, M.; MINBIOLE, Kevin, P.C.; BARBAY, Deanna, L.; (227 pag.)WO2016/172436; (2016); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound.

The compound having the structure shown in Formula (II) of FIG. 4 was made using the scheme set forth in FIG. 1. First, alpha-Dimethylaminoethylferrocene, (14.30 g, 55.61 mmol), (as Compound 1) was dissolved in solvent (85 ml) under argon. N-butyl lithium (1.6 M) was added slowly (22.6 ml, 66.73 mmol, 1.2 eq.) and the reaction was stirred at room temperature for one hour. The solution was then purged with argon for thirty minutes. Chlorodiphenylphosphine (12.0 ml, 66.73 mmol, 1.2 eq.) in tert-butyl methyl ether (10 ml) was added slowly, and the reaction stirred at room temperature for four hours. The reaction was cooled to 0 C., and saturated sodium bicarbonate solution (57 ml) was added followed by water (45 ml). The composition separated into aqueous and organic phases, and the aqueous layer was removed and washed with toluene, and the resulting toluene was separated from the aqueous layer and combined with the organic layer, with the resulting composition being was dried over magnesium sulfate. The magnesium sulfate hydrate was then removed by filtration. The resulting filtrate solution was concentrated under vacuum to give an orange oil. The resulting oil was dissolved in ethanol and then solvents were removed under vacuum once more. The oil was then recrystallized by dissolving in the minimum amount of hot ethanol (45 ml) and cooling to room temperature. The resulting product, present as an orange solid, contained compound 2, which was 1-alpha-dimethyl-aminoethyl-2-(diphenylphosphino)ferrocene (9.16 g, 20.7 mmol, 31% yield).

The chemical industry reduces the impact on the environment during synthesis,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Eastman Chemical Company; How, Rebecca; Clarke, Matt; Hembre, Robert Thomas; Ponasik, James A.; Tolleson, Ginette S.; (17 pag.)US9308527; (2016); B2;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis