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Orellanine II CAS:72016-31-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediat
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Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryfactory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
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ORELLANINEAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express
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3,3'-dihydroxy-2,2'-bipyridine-4,4'(1H,1'H)-dione CAS 72016-31-0 Orellanine II Appearance:White powder. Storage:Stool in cool and dry place. Package:as per customers' request. Application:Reagents, intermediates, laboratory and
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3,3',4,4'-tetramethoxy-2,2'-bipyridine
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 77% |
With hydrogen bromide at 150℃; sealed tube, overnight; | 60% |
With hydrogen bromide at 120℃; | 60% |
3,3'-Bis<<2-(trimethylsilyl)ethoxy>methoxy>-2,2'-bipyridin-4,4'-diol
orelline
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 1h; Heating; | 75% |
4,4'-dihydroxy-3,3'-dimethoxy-2,2'-bipyridine
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 71% |
3,3'-dihyroxy-4,4'-dimethoxy-2,2'-bipyridyl
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 70% |
3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
orelline
Conditions | Yield |
---|---|
at 220℃; under 0.01 Torr; sublimation; | 50% |
for 336h; Irradiation; |
3,3'-Dihydroxy-2,2'-bipyridin-4,4'-dicarbaldehyd
orelline
Conditions | Yield |
---|---|
With dihydrogen peroxide In potassium hydroxide at 60 - 70℃; for 1h; | 36% |
orelline
Conditions | Yield |
---|---|
With bis-trimethylsilanyl peroxide In diethyl ether for 0.5h; Ambient temperature; | 11% |
Multi-step reaction with 3 steps 1: 45 percent / 0.5 h / -20 - -15 °C 2: 75 percent / conc. HCl / H2O / 30 h / Heating 3: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 10 percent / 0.5 h / -5 °C 2: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 10 percent / bis(trimethylsilyl)-peroxide / 0.5 h / -5 °C 2: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme |
2-iodo-3-hydroxypyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 70 percent / NaH / dimethylsulfoxide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 5.1: aq. HCl / diethyl ether / 15 h / 20 °C 6.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 4.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 5.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 6.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 4.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 5.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-methoxy-pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 3.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 4.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 5.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 3.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 4.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-(methoxymethoxy)pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 4.1: aq. HCl / diethyl ether / 15 h / 20 °C 5.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3,4-dimethoxypyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 1.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 2.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-methoxypyridin-4-ol
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 2.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 3.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 4.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 2.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 3.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-methoxy-4-(methoxymethoxy)pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 1.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 2.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 3.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-4-methoxy-3-(methoxymethoxy)pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 2: aq. HCl / diethyl ether / 15 h / 20 °C 3: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-(methoxymethoxy)pyridin-4-ol
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 2: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 3: aq. HCl / diethyl ether / 15 h / 20 °C 4: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 2: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. HCl / diethyl ether / 15 h / 20 °C 2: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
3-HYDROXYPYRIDINE
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 52 percent / Br2, HCl / aq. NaOH / 20 °C 2: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 3: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 4: 22 percent / 1.) 1.5 M BuLi; 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) Et2O, -50 deg C, hexan, 2h; 2.) -20 deg C, THF, 75 min 5: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1: 52 percent / Br2, HCl / aq. NaOH / 20 °C 2: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 3: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 4: 1.5 M BuLi / diethyl ether / -50 - -20 °C 5: 45 percent / 0.5 h / -20 - -15 °C 6: 75 percent / conc. HCl / H2O / 30 h / Heating 7: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 6 steps 1: 52 percent / Br2, HCl / aq. NaOH / 20 °C 2: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 3: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 4: 1.5 M BuLi / diethyl ether / -50 - -20 °C 5: 10 percent / 0.5 h / -5 °C 6: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme |
2-bromo-pyridin-3-ol
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 2: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 3: 22 percent / 1.) 1.5 M BuLi; 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) Et2O, -50 deg C, hexan, 2h; 2.) -20 deg C, THF, 75 min 4: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 2: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 3: 1.5 M BuLi / diethyl ether / -50 - -20 °C 4: 45 percent / 0.5 h / -20 - -15 °C 5: 75 percent / conc. HCl / H2O / 30 h / Heating 6: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF, 25 deg C, 1 h; 2.) 1.5 h 2: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 3: 1.5 M BuLi / diethyl ether / -50 - -20 °C 4: 10 percent / 0.5 h / -5 °C 5: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme |
2-bromo-3-(β-trimethylsilyl ethoxymethoxy)pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 2: 22 percent / 1.) 1.5 M BuLi; 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) Et2O, -50 deg C, hexan, 2h; 2.) -20 deg C, THF, 75 min 3: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 2: 1.5 M BuLi / diethyl ether / -50 - -20 °C 3: 45 percent / 0.5 h / -20 - -15 °C 4: 75 percent / conc. HCl / H2O / 30 h / Heating 5: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 4 steps 1: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 2: 1.5 M BuLi / diethyl ether / -50 - -20 °C 3: 10 percent / 0.5 h / -5 °C 4: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 2: 1.5 M BuLi / diethyl ether / -50 - -20 °C 3: 10 percent / bis(trimethylsilyl)-peroxide / 0.5 h / -5 °C 4: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 79 percent / NiCl2*6H2O, triphenylphosphine, Zn / dimethylformamide / 0.42 h / 60 °C 2: 1.5 M BuLi / diethyl ether / -50 - -20 °C 3: 11 percent / bis(trimethylsilyl)-peroxide / diethyl ether / 0.5 h / Ambient temperature View Scheme |
3,3'-Bis<<2-(trimethylsilyl)ethoxy>methoxy>-2,2'-bipyridin
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 22 percent / 1.) 1.5 M BuLi; 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) Et2O, -50 deg C, hexan, 2h; 2.) -20 deg C, THF, 75 min 2: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 1.5 M BuLi / diethyl ether / -50 - -20 °C 2: 45 percent / 0.5 h / -20 - -15 °C 3: 75 percent / conc. HCl / H2O / 30 h / Heating 4: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1.5 M BuLi / diethyl ether / -50 - -20 °C 2: 10 percent / 0.5 h / -5 °C 3: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 1.5 M BuLi / diethyl ether / -50 - -20 °C 2: 10 percent / bis(trimethylsilyl)-peroxide / 0.5 h / -5 °C 3: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 1.5 M BuLi / diethyl ether / -50 - -20 °C 2: 11 percent / bis(trimethylsilyl)-peroxide / diethyl ether / 0.5 h / Ambient temperature View Scheme |
3,3'-Bis<<2-(trimethylsilyl)ethoxy>methoxy>-2,2'-bipyridin-4,4'-dicarbaldehyd
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / conc. HCl / H2O / 30 h / Heating 2: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme |
2-bromo-3,4-dimethoxy pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C 2: 60 percent / 48percent HBr / 120 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 2: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 3: 60 percent / 48percent aq. HBr / 5 h / 120 °C 4: 50 percent / 220 °C / 0.01 Torr / sublimation View Scheme | |
Multi-step reaction with 2 steps 1: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 2: 60 percent / 48percent aq. HBr / 150 °C / sealed tube, overnight View Scheme |
2-bromo-3,4-dimethoxy pyridine-N-oxide
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus tribromide 2: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C 3: 60 percent / 48percent HBr / 120 °C View Scheme | |
Multi-step reaction with 5 steps 1: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 2: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 3: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 4: 60 percent / 48percent aq. HBr / 5 h / 120 °C 5: 50 percent / 220 °C / 0.01 Torr / sublimation View Scheme | |
Multi-step reaction with 3 steps 1: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 2: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 3: 60 percent / 48percent aq. HBr / 150 °C / sealed tube, overnight View Scheme |
4-methoxypyridin-3-amine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 80 percent / Br2, conc. HCl / 1 h 3: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C 4: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C 5: 92 percent / Na / 0.25 h / Heating 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 7: 336 h / Irradiation View Scheme |
2-chloro-3-fluoropyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 7: 336 h / Irradiation View Scheme | |
Multi-step reaction with 5 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 8 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 83 percent / Na / methanol / 72 h / Ambient temperature 4: 80 percent / PCl3 / CHCl3 / 2 h / Heating 5: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 6: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 7: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 8: 336 h / Irradiation View Scheme | |
Multi-step reaction with 6 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 83 percent / Na / methanol / 72 h / Ambient temperature 4: 80 percent / PCl3 / CHCl3 / 2 h / Heating 5: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 6: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1: 54 percent / acetic anhydride, 30percent H2O2 2: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 3: Ambient temperature 4: PCl3 5: 25 percent / dimethylformamide / 4 h / 50 °C 6: 46 percent / 33percent HBr / acetic acid / 4 h View Scheme |
2-Chlor-3-fluorpyridin-1-oxid
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 6: 336 h / Irradiation View Scheme | |
Multi-step reaction with 4 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 83 percent / Na / methanol / 72 h / Ambient temperature 3: 80 percent / PCl3 / CHCl3 / 2 h / Heating 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 7: 336 h / Irradiation View Scheme | |
Multi-step reaction with 5 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 83 percent / Na / methanol / 72 h / Ambient temperature 3: 80 percent / PCl3 / CHCl3 / 2 h / Heating 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 2: Ambient temperature 3: PCl3 4: 25 percent / dimethylformamide / 4 h / 50 °C 5: 46 percent / 33percent HBr / acetic acid / 4 h View Scheme |
2-chloro-3,4-dimethoxypyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 2: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 3: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 4: 336 h / Irradiation View Scheme | |
Multi-step reaction with 2 steps 1: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 2: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 25 percent / dimethylformamide / 4 h / 50 °C 2: 46 percent / 33percent HBr / acetic acid / 4 h View Scheme |
2-Chlor-3,4-dimethoxypyridin-1-oxid
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 80 percent / PCl3 / CHCl3 / 2 h / Heating 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 5: 336 h / Irradiation View Scheme | |
Multi-step reaction with 3 steps 1: 80 percent / PCl3 / CHCl3 / 2 h / Heating 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: PCl3 2: 25 percent / dimethylformamide / 4 h / 50 °C 3: 46 percent / 33percent HBr / acetic acid / 4 h View Scheme |
2-Chlor-3-fluor-4-nitropyridin-1-oxid
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 5: 336 h / Irradiation View Scheme | |
Multi-step reaction with 3 steps 1: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1: 83 percent / Na / methanol / 72 h / Ambient temperature 2: 80 percent / PCl3 / CHCl3 / 2 h / Heating 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating 6: 336 h / Irradiation View Scheme | |
Multi-step reaction with 4 steps 1: 83 percent / Na / methanol / 72 h / Ambient temperature 2: 80 percent / PCl3 / CHCl3 / 2 h / Heating 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 46 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: Ambient temperature 2: PCl3 3: 25 percent / dimethylformamide / 4 h / 50 °C 4: 46 percent / 33percent HBr / acetic acid / 4 h View Scheme |
orelline
3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
Conditions | Yield |
---|---|
With dihydrogen peroxide for 8h; Ambient temperature; | 87% |
for 336h; Irradiation; isomerisation also without irradiation; |
diazomethane
orelline
3,3'-dihyroxy-4,4'-dimethoxy-2,2'-bipyridyl
Conditions | Yield |
---|---|
In diethyl ether Ambient temperature; |
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