Product Name

  • Name

    SANGUINARINE CHLORIDE

  • EINECS
  • CAS No. 5578-73-4
  • Article Data12
  • CAS DataBase
  • Density g/cm3
  • Solubility
  • Melting Point 281-285°C
  • Formula C20H14 N O4 . Cl
  • Boiling Point °Cat760mmHg
  • Molecular Weight 367.788
  • Flash Point °C
  • Transport Information
  • Appearance
  • Safety A poison by intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl−.
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 5578-73-4 (SANGUINARINE CHLORIDE)
  • Hazard Symbols Moderately toxic by ingestion.
  • Synonyms Sanguinarine,chloride (6CI,8CI); [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (9CI);13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride;Sanguinarine hydrochloride; Sanguinarium chloride
  • PSA 40.80000
  • LogP 0.43210

Synthetic route

oxysanguinarine
548-30-1

oxysanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Stage #1: oxysanguinarine With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃;		98%
dihydrosanguinarine
3606-45-9

dihydrosanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; jones reagent In acetone at 0℃; for 0.5h;85.4%
With sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene
With sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; benzene for 1h; Ambient temperature;2.1 g
Stage #1: dihydrosanguinarine With 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide In toluene at 20℃; for 2h;
Stage #2: With hydrogenchloride
Stage #1: dihydrosanguinarine With 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide In water; toluene at 20℃; for 1h;
Stage #2: With hydrogenchloride In chloroform; water at 0℃;
C20H17NO4
22855-18-1, 107651-16-1

C20H17NO4

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; maleic acid In water; acetic acid47%
norsanguinarine
522-30-5

norsanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
(methylation);
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / 40 °C
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide / toluene; water / 1 h / 20 °C
2.2: 0 °C
View Scheme
sanguinarine hydrosulfate

sanguinarine hydrosulfate

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
With hydrogenchloride In water Heating;
dihydrosanguinarine

dihydrosanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
With iron(III) chloride
O-acetyl-chelidonine

O-acetyl-chelidonine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
With mercury(II) diacetate
(+)-chelidonine

(+)-chelidonine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 9.8 g / pyridine / 6 h / Ambient temperature
2: HgO / acetic acid / 4 h / Heating
3: 2.1 g / 2,3-dichloro-5,6-dicyano-p-benzoquinone, 5percent NaOH / benzene; H2O / 1 h / Ambient temperature
View Scheme
(+)-chelidonine acetate

(+)-chelidonine acetate

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HgO / acetic acid / 4 h / Heating
2: 2.1 g / 2,3-dichloro-5,6-dicyano-p-benzoquinone, 5percent NaOH / benzene; H2O / 1 h / Ambient temperature
View Scheme
13-methyl-6,7,13,14-tetrahydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
22855-17-0

13-methyl-6,7,13,14-tetrahydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd-C
2: DDQ, aq. NaOH / benzene
View Scheme
8-hydroxydihydosanguinarine
4070-41-1

8-hydroxydihydosanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Acidic aq. solution;
methyl 5-iodobenzo[d][1,3]dioxole-4-carboxylate
33842-29-4

methyl 5-iodobenzo[d][1,3]dioxole-4-carboxylate

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere
2.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
4.2: 20 °C
View Scheme
C8H4ClIO3

C8H4ClIO3

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 0.5 h / Inert atmosphere
2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere
3.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
5.2: 20 °C
View Scheme
7,8-methylenedioxy-13,14-cis-dihydrobenzodioxolebenzo[c]phenanthridin-6-one

7,8-methylenedioxy-13,14-cis-dihydrobenzodioxolebenzo[c]phenanthridin-6-one

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
3.2: 20 °C
View Scheme
C20H15NO5

C20H15NO5

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 20 °C
View Scheme
5-iodobenzo[d][1,3]dioxole-4-carboxylic acid
1309123-33-8

5-iodobenzo[d][1,3]dioxole-4-carboxylic acid

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere
2.1: 0.5 h / Inert atmosphere
3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere
4.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
6.2: 20 °C
View Scheme
5-iodobenzo[d][1,3]dioxole-4-carbaldehyde
249636-72-4

5-iodobenzo[d][1,3]dioxole-4-carbaldehyde

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dihydrogen peroxide; potassium hydroxide / methanol; water / 0.5 h / 65 °C / Inert atmosphere
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere
3.1: 0.5 h / Inert atmosphere
4.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere
5.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
7.2: 20 °C
View Scheme
sanguinarine acetate
55438-13-6

sanguinarine acetate

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Stage #1: sanguinarine acetate With potassium hydroxide In water
Stage #2: With hydrogenchloride In water
7-methyl-5H-indeno[5,6-d][1,3]dioxole

7-methyl-5H-indeno[5,6-d][1,3]dioxole

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
2: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
3: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
4: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
5: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
2: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
3: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
4: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
5: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
5,6-methylenedioxy-1-indanone
6412-87-9

5,6-methylenedioxy-1-indanone

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: cerium(III) chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / Inert atmosphere
3.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
4.1: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
5.1: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
6.1: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
7.1: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: cerium(III) chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / Inert atmosphere
3.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
4.1: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
5.1: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
6.1: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
7.1: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
2-(6-acetylbenzo[d][1,3]dioxol-5-yl)acetaldehyde

2-(6-acetylbenzo[d][1,3]dioxol-5-yl)acetaldehyde

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
2: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
3: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
2: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
3: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
5-bromo-benzo[1,3]dioxole-4-carbaldehyde
72744-54-8

5-bromo-benzo[1,3]dioxole-4-carbaldehyde

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: methanol / 3 h / 20 °C / Inert atmosphere
2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
3: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
4: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
5: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: methanol / 3 h / 20 °C / Inert atmosphere
2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
3: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
4: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
5: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C
2.1: pyridine; phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 110 °C
4.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 16 h / 90 - 110 °C / Inert atmosphere
5.1: sodium tetrahydroborate / 40 °C
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide / toluene; water / 1 h / 20 °C
6.2: 0 °C
View Scheme
1-(5-bromobenzo[d][1,3]dioxol-4-yl)-N-methylmethanamine

1-(5-bromobenzo[d][1,3]dioxol-4-yl)-N-methylmethanamine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
2: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
3: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
2: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
3: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
C9H8BrNO2
1207666-53-2

C9H8BrNO2

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
2: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
3: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
4: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
2: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
3: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
4: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
N-((5-bromobenzo[d][1,3]dioxol-4-yl)methyl)-N-methylnaphtho[2,3-d][1,3]dioxol-5-amine

N-((5-bromobenzo[d][1,3]dioxol-4-yl)methyl)-N-methylnaphtho[2,3-d][1,3]dioxol-5-amine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
2: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
C11H12O3

C11H12O3

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / Inert atmosphere
2: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
3: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
4: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
5: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
6: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / Inert atmosphere
2: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h
3: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
4: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
5: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
6: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
7-methyl-5H-indeno[5,6-d][1,3]dioxole

7-methyl-5H-indeno[5,6-d][1,3]dioxole

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
2: zinc(II) chloride / dichloromethane; diethyl ether / 18 h / 55 °C / Inert atmosphere; Microwave irradiation
3: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
4: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: IO4(1-)*Na(1+)*O2Si / dichloromethane / 1 h / Inert atmosphere
2: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane / 36 h / 55 °C / Inert atmosphere; Microwave irradiation
3: 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique
4: sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 20 °C
View Scheme
2,3-methylenedioxy-5-nitronaphthalene
142886-75-7

2,3-methylenedioxy-5-nitronaphthalene

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr
2.1: potassium carbonate / N,N-dimethyl-formamide / 110 °C
3.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 16 h / 90 - 110 °C / Inert atmosphere
4.1: sodium tetrahydroborate / 40 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide / toluene; water / 1 h / 20 °C
5.2: 0 °C
View Scheme
naphtho[2,3-d][1,3]dioxol-5-amine
53811-49-7

naphtho[2,3-d][1,3]dioxol-5-amine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 110 °C
2.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 16 h / 90 - 110 °C / Inert atmosphere
3.1: sodium tetrahydroborate / 40 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide / toluene; water / 1 h / 20 °C
4.2: 0 °C
View Scheme
N-(6'-bromo-2',3'-methylenedioxybenzyl)-6,7-methylenedioxy-1-naphthylamine
93666-99-0

N-(6'-bromo-2',3'-methylenedioxybenzyl)-6,7-methylenedioxy-1-naphthylamine

sanguinarine chloride
5578-73-4

sanguinarine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 16 h / 90 - 110 °C / Inert atmosphere
2.1: sodium tetrahydroborate / 40 °C
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide / toluene; water / 1 h / 20 °C
3.2: 0 °C
View Scheme
sanguinarine chloride
5578-73-4

sanguinarine chloride

butan-1-ol
71-36-3

butan-1-ol

6-butoxy-5,6-dihydrosanguinarine
49702-43-4

6-butoxy-5,6-dihydrosanguinarine

Conditions
ConditionsYield
With copper(II) chloride dihydrate; oxygen at 80℃; for 10h;99%
With sodium carbonate In water
propan-1-ol
71-23-8

propan-1-ol

sanguinarine chloride
5578-73-4

sanguinarine chloride

13-methyl-14-propoxy-13,14-dihydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
49702-42-3

13-methyl-14-propoxy-13,14-dihydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine

Conditions
ConditionsYield
With copper(II) chloride dihydrate; oxygen at 80℃; for 10h;99%
sanguinarine chloride
5578-73-4

sanguinarine chloride

isopropyl alcohol
67-63-0

isopropyl alcohol

C23H21NO5
1292824-30-6, 1333222-84-6, 1333222-85-7

C23H21NO5

Conditions
ConditionsYield
With copper(II) chloride dihydrate; oxygen at 80℃; for 10h;98%
ethanol
64-17-5

ethanol

sanguinarine chloride
5578-73-4

sanguinarine chloride

6-Ethoxy-5,6-dihydrosanguinarine
28342-31-6

6-Ethoxy-5,6-dihydrosanguinarine

Conditions
ConditionsYield
With copper(II) chloride dihydrate; oxygen at 80℃; for 10h;97%
methanol
67-56-1

methanol

sanguinarine chloride
5578-73-4

sanguinarine chloride

6-methoxy-5,6-dihydrosanguinarine
72401-54-8, 88544-84-7

6-methoxy-5,6-dihydrosanguinarine

Conditions
ConditionsYield
With copper(II) chloride dihydrate; oxygen at 80℃; for 10h;96%
potassium cyanide

potassium cyanide

sanguinarine chloride
5578-73-4

sanguinarine chloride

sanguinarine φ-cyanide
23701-59-9

sanguinarine φ-cyanide

Conditions
ConditionsYield
In water at 60℃; for 0.5h;83%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

sanguinarine chloride
5578-73-4

sanguinarine chloride

sanguinarine φ-cyanide
23701-59-9

sanguinarine φ-cyanide

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃;59%
sanguinarine chloride
5578-73-4

sanguinarine chloride

dihydrosanguinarine
3606-45-9

dihydrosanguinarine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 20℃; for 0.5h; Darkness;55%
With sodium tetrahydroborate In methanol at 20℃; for 0.5h;36%
With 1,4-dihydronicotinamide adenine dinucleotide In water at 25℃; Rate constant; Kinetics; Thermodynamic data; other coenzyme, var. pH, ΔH(excit.), ΔS(excit.);
With sodium tetrahydroborate In methanol
sodium methylate
124-41-4

sodium methylate

sanguinarine chloride
5578-73-4

sanguinarine chloride

6-methoxy-5,6-dihydrosanguinarine
72401-54-8, 88544-84-7

6-methoxy-5,6-dihydrosanguinarine

Conditions
ConditionsYield
In methanol for 6h; pH=10; Reflux;51%
sanguinarine chloride
5578-73-4

sanguinarine chloride

9H-carbazole
86-74-8

9H-carbazole

6-(carbazol-1-yl)-5,6-dihydrosanguinarine
1452540-22-5

6-(carbazol-1-yl)-5,6-dihydrosanguinarine

Conditions
ConditionsYield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran Inert atmosphere; Sonication;
Stage #2: sanguinarine chloride In tetrahydrofuran at 20℃;		45%
sanguinarine chloride
5578-73-4

sanguinarine chloride

oxysanguinarine
548-30-1

oxysanguinarine

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide; potassium hexacyanoferrate(III) In water at 90℃; for 3h;43%
With sodium hydroxide
methylmagnesium bromide
75-16-1

methylmagnesium bromide

sanguinarine chloride
5578-73-4

sanguinarine chloride

C21H17NO4

C21H17NO4

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 10h;29%
indole
120-72-9

indole

sanguinarine chloride
5578-73-4

sanguinarine chloride

14-(1H-indol-3-yl)-13-methyl-13,14-dihydro[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine

14-(1H-indol-3-yl)-13-methyl-13,14-dihydro[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine

Conditions
ConditionsYield
With triethylamine In acetonitrile for 10h; Reflux;17.4%
potassium cyanide
151-50-8

potassium cyanide

sanguinarine chloride
5578-73-4

sanguinarine chloride

sanguinarine φ-cyanide
23701-59-9

sanguinarine φ-cyanide

Conditions
ConditionsYield
With water
sanguinarine chloride
5578-73-4

sanguinarine chloride

benzyl alcohol
100-51-6

benzyl alcohol

norsanguinarine
522-30-5

norsanguinarine

sanguinarine chloride
5578-73-4

sanguinarine chloride

8-hydroxydihydosanguinarine
4070-41-1

8-hydroxydihydosanguinarine

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
sanguinarine chloride
5578-73-4

sanguinarine chloride

acetone
67-64-1

acetone

(+/-)-6-acetonyldihydrosanguinarine
37687-34-6, 88588-10-7

(+/-)-6-acetonyldihydrosanguinarine

Conditions
ConditionsYield
With sodium carbonate Heating;
sanguinarine chloride
5578-73-4

sanguinarine chloride

norsanguinarine
522-30-5

norsanguinarine

Conditions
ConditionsYield
at 207℃; for 0.116667h;
sanguinarine chloride
5578-73-4

sanguinarine chloride

bis<6-(5,6-dihydrosanguinarinyl)> ether

bis<6-(5,6-dihydrosanguinarinyl)> ether

Conditions
ConditionsYield
With sodium carbonate In water
sanguinarine chloride
5578-73-4

sanguinarine chloride

C20H12(2)H3NO4

C20H12(2)H3NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.12 h / 207 °C
2: 1.3 g / NaBH4 / hexamethylphosphoric acid triamide / 2 h / 50 °C
View Scheme

Sanguinarine chloride Chemical Properties

Synonyms:  13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium Chloride ; Pseudochelerythrine chloride ; Sanguinarine chloride ; Sanguinarine chloride hydrate ; Sanguinarine chloride ; Sanguinarine, chloride ; Sanguinarium chloride ; Sanguinarium chloride
The Molecular Formula of  Sanguinarine chloride (CAS NO.5578-73-4):C20H14ClNO4
The Molecular Weight of  Sanguinarine chloride (CAS NO.5578-73-4):367.782460 g/mol
The Molecular Structure of  Sanguinarine chloride (CAS NO.5578-73-4):
Melting Point:281-285°C
Solubility: methanol, 20 mg/mL, clear, orange
Polar Surface Area: 40.8 Å2 

Sanguinarine chloride Uses

   Sanguinarine chloride ,whose Cas Register Number is 5578-73-4,can be used as cardiotonic agent.

Sanguinarine chloride Toxicity Data With Reference

1.    

orl-rat LD50:1658 mg/kg

     JTEHD6    Journal of Toxicology and Environmental Health. 20 (1987),199.
2.    

ipr-rat LDLo:20 mg/kg

     NATUAS    Nature. 162 (1948),265.
3.    

ivn-rat LD50:29 mg/kg

     JTEHD6    Journal of Toxicology and Environmental Health. 20 (1987),199.
4.    

scu-mus LD50:102 mg/kg

     PLMEAA    Planta Medica. 43 (1981),161.
5.    

ivn-mus LD50:15900 µg/kg

     PLMEAA    Planta Medica. 43 (1981),161.

Sanguinarine chloride Safety Profile

A poison by intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl−.
Hazard Codes:HarmfulXn
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 36 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: VP5220000
F: 10

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