Product Name

  • Name

    orellanine

  • EINECS
  • CAS No. 37338-80-0
  • Article Data4
  • CAS DataBase
  • Density 1.777 g/cm3
  • Solubility
  • Melting Point
  • Formula C10H8N2O6
  • Boiling Point 834.615 °C at 760 mmHg
  • Molecular Weight 252.183
  • Flash Point 458.558 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 37338-80-0 (orellanine)
  • Hazard Symbols
  • Synonyms 3,3',4,4'-Tetrahydroxy-2,2'-bipyridine-1,1'-dioxide;
  • PSA 124.92000
  • LogP -0.43720

Synthetic route

orelline
72016-31-0

orelline

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
With dihydrogen peroxide for 8h; Ambient temperature;87%
for 336h; Irradiation; isomerisation also without irradiation;
tetra-O-methylorellanine
101664-54-4

tetra-O-methylorellanine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid for 5h; Heating;77%
With hydrogen bromide at 120℃; for 5h;60%
With hydrogen bromide at 120℃;60%
With hydrogen bromide In acetic acid for 4h;30%
3,3',4,4'-tetramethoxy-2,2'-bipyridine
101664-55-5

3,3',4,4'-tetramethoxy-2,2'-bipyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: m-chloroperbenzoic acid
2: m-chloroperbenzoic acid
3: 60 percent / 48percent HBr / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C
2: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
2: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: 41 percent / Ac2O, H2O2
2: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-bromo-3,4-dimethoxy pyridine
104819-52-5

2-bromo-3,4-dimethoxy pyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C
2: m-chloroperbenzoic acid
3: m-chloroperbenzoic acid
4: 60 percent / 48percent HBr / 120 °C
View Scheme
Multi-step reaction with 3 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
View Scheme
2-bromo-3,4-dimethoxy pyridine-N-oxide
105011-83-4

2-bromo-3,4-dimethoxy pyridine-N-oxide

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: phosphorus tribromide
2: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C
3: m-chloroperbenzoic acid
4: m-chloroperbenzoic acid
5: 60 percent / 48percent HBr / 120 °C
View Scheme
Multi-step reaction with 4 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
View Scheme
3,4,3',4'-Tetramethoxy-[2,2']bipyridinyl 1-oxide
112516-35-5

3,4,3',4'-Tetramethoxy-[2,2']bipyridinyl 1-oxide

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: m-chloroperbenzoic acid
2: 60 percent / 48percent HBr / 120 °C
View Scheme
4-methoxypyridin-3-amine
33631-09-3

4-methoxypyridin-3-amine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
2-chloro-3-fluoropyridine
17282-04-1

2-chloro-3-fluoropyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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: 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
View Scheme
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: 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
View Scheme
Multi-step reaction with 7 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: 41 percent / Ac2O, H2O2
7: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-Chlor-3-fluorpyridin-1-oxid
85386-94-3

2-Chlor-3-fluorpyridin-1-oxid

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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: 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
View Scheme
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: 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
View Scheme
Multi-step reaction with 6 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: 41 percent / Ac2O, H2O2
6: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-chloro-3,4-dimethoxypyridine
101664-59-9

2-chloro-3,4-dimethoxypyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
Multi-step reaction with 3 steps
1: 25 percent / dimethylformamide / 4 h / 50 °C
2: 41 percent / Ac2O, H2O2
3: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-Chlor-3,4-dimethoxypyridin-1-oxid
101664-58-8

2-Chlor-3,4-dimethoxypyridin-1-oxid

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
Multi-step reaction with 4 steps
1: PCl3
2: 25 percent / dimethylformamide / 4 h / 50 °C
3: 41 percent / Ac2O, H2O2
4: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-Chlor-3-fluor-4-nitropyridin-1-oxid
101664-56-6

2-Chlor-3-fluor-4-nitropyridin-1-oxid

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
Multi-step reaction with 5 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
View Scheme
Multi-step reaction with 5 steps
1: Ambient temperature
2: PCl3
3: 25 percent / dimethylformamide / 4 h / 50 °C
4: 41 percent / Ac2O, H2O2
5: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-bromo-3-fluoro-4-methoxypyridine
109613-98-1

2-bromo-3-fluoro-4-methoxypyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C
2: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C
3: 92 percent / Na / 0.25 h / Heating
4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating
View Scheme
2-bromo-4-methoxy-pyridin-3-amine
109613-97-0

2-bromo-4-methoxy-pyridin-3-amine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C
3: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C
4: 92 percent / Na / 0.25 h / Heating
5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating
View Scheme
3,3'-Difluor-4,4'-dimethoxy-2,2'-bipyridin
109613-99-2

3,3'-Difluor-4,4'-dimethoxy-2,2'-bipyridin

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C
2: 92 percent / Na / 0.25 h / Heating
3: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating
View Scheme
3,3'-Difluor-4,4'-dimethoxy-<2,2'-bipyridin>-1,1'-dioxid
109613-94-7

3,3'-Difluor-4,4'-dimethoxy-<2,2'-bipyridin>-1,1'-dioxid

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / Na / 0.25 h / Heating
2: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating
View Scheme
3-HYDROXYPYRIDINE
109-00-2

3-HYDROXYPYRIDINE

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 35 percent / Br2, 10percent aq. NaOH / 24 h
2: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h
3: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature
4: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C
5: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
6: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
7: 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
8: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
9: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
3-hydroxypyridine N-oxide
6602-28-4

3-hydroxypyridine N-oxide

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) Br2; 2.) NaOCH3 / 1.) 10percent aq. NaOH, 24 h; 2.) MeOH, DMF, RT, 1.5 h
2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C
3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
5: 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
6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
7: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
2-bromo-pyridin-3-ol
6602-32-0

2-bromo-pyridin-3-ol

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h
2: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature
3: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C
4: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
5: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
6: 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
7: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
8: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
2-bromo-3-methoxypyridine
24100-18-3

2-bromo-3-methoxypyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature
2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C
3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
5: 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
6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
7: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
2-bromo-3-methoxypyridine N-oxide
104819-48-9

2-bromo-3-methoxypyridine N-oxide

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C
2: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
3: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
4: 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
5: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
6: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
2-bromo,3-methoxy,4-nitropyridine-N-oxide
104819-50-3

2-bromo,3-methoxy,4-nitropyridine-N-oxide

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature
2: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C
3: 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
4: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature
5: 60 percent / 48percent aq. HBr / 5 h / 120 °C
View Scheme
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 82 percent / 15percent H2O2, conc. HCl
2: 38 percent
3: 54 percent / acetic anhydride, 30percent H2O2
4: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3
5: Ambient temperature
6: PCl3
7: 25 percent / dimethylformamide / 4 h / 50 °C
8: 41 percent / Ac2O, H2O2
9: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
2-chloro-3-aminopyridine
6298-19-7

2-chloro-3-aminopyridine

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 38 percent
2: 54 percent / acetic anhydride, 30percent H2O2
3: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3
4: Ambient temperature
5: PCl3
6: 25 percent / dimethylformamide / 4 h / 50 °C
7: 41 percent / Ac2O, H2O2
8: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h
View Scheme
3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

orelline
72016-31-0

orelline

Conditions
ConditionsYield
at 220℃; under 0.01 Torr; sublimation;50%
for 336h; Irradiation;
diazomethane
186581-53-3, 908094-01-9

diazomethane

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

A

tetra-O-methylorellanine
101664-54-4

tetra-O-methylorellanine

B

1,3,3',4'-Tetramethoxy<2,2'-bipyridin>-4(1H)-on-1'-oxid
109613-96-9

1,3,3',4'-Tetramethoxy<2,2'-bipyridin>-4(1H)-on-1'-oxid

C

1,1',3,3'-Tetramethoxy<2,2'-bipyridin>-4,4'(1H,1'-H)-dion
109613-95-8

1,1',3,3'-Tetramethoxy<2,2'-bipyridin>-4,4'(1H,1'-H)-dion

Conditions
ConditionsYield
In methanol; diethyl etherA 18%
B 16%
C 16%
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3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

C10H8N2O5

C10H8N2O5

Conditions
ConditionsYield
at 180 - 200℃;
3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

orellanine anion radical

orellanine anion radical

Conditions
ConditionsYield
With phosphate buffer; oxygen for 0.0166667h; Ambient temperature; tyrosinase;

Orellanine Specification

The CAS registry number of [2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide is 37338-80-0. It is a pyridine N-oxide and a crystalline alkaloid that is found naturally in some lifeforms. In addition, the molecular formula is C10H8N2O6 and the molecular weight is 252.17. What's more, it has been found in at least five species of mushrooms in the Cortinariaceae family.

Physical properties about [2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide are: (1)ACD/LogP: -3.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4; (4)ACD/LogD (pH 7.4): -7; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 131.84 Å2; (13)Index of Refraction: 1.728; (14)Molar Refractivity: 56.554 cm3; (15)Molar Volume: 141.911 cm3; (16)Polarizability: 22.42 ×10-24cm3; (17)Surface Tension: 86.76 dyne/cm; (18)Density: 1.777 g/cm3; (19)Flash Point: 458.558 °C; (20)Enthalpy of Vaporization: 125.458 kJ/mol; (21)Boiling Point: 834.615 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][n+]1ccc(O)c(O)c1c2[n+]([O-])ccc(O)c2O
(2)Std. InChI: InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,13-16H
(3)Std. InChIKey: JEWWXPOUSBVQKG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 4900ug/kg (4.9mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.
guinea pig LD50 intraperitoneal 8mg/kg (8mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.
mouse LD50 intraperitoneal 12480ug/kg (12.48mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.
mouse LD50 oral 33mg/kg (33mg/kg)   Archives of Toxicology. Vol. 62, Pg. 81, 1988.
mouse LD50 subcutaneous 8300ug/kg (8.3mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.

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