Product Name

  • Name

    Carvedilol

  • EINECS 1308068-626-2
  • CAS No. 72956-09-3
  • Article Data46
  • CAS DataBase
  • Density 1.25 g/cm3
  • Solubility 449.2ug/L(22.5 oC)
  • Melting Point 113-117 °C
  • Formula C24H26N2O4
  • Boiling Point 655.2 °C at 760 mmHg
  • Molecular Weight 496.517
  • Flash Point 350.1 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance colourless crystalline powder
  • Safety 61-36-26
  • Risk Codes 51/53-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 72956-09-3 (Carvedilol)
  • Hazard Symbols HarmfulXn, DangerousN
  • Synonyms 2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)-;Carvedilolum [Latin];Carvedilol [USAN:BAN:INN:JAN];Coreg (TN);Carvedilol (JAN/USAN);2-Propanol,1-(9H-carbazol-4-yloxy)-3-[[2- (2-methoxyphenoxy)ethyl]amino]-;SKF 105517;(+-)-1-(Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol;DQ 2466;1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol;
  • PSA 75.74000
  • LogP 4.12890

Synthetic route

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate
787598-91-8

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate

A

C39H39N3O6
918903-20-5

C39H39N3O6

B

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 50 - 70℃; for 0.75h;A n/a
B 91.21%
Stage #1: (+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate With triethylamine In ethyl acetate at 10 - 35℃; for 1h;
Stage #2: With sodium chloride In water; ethyl acetate for 0.5h;
5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one
180987-80-8

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium hydroxide In propan-1-ol at 60℃; for 4h; Solvent; Temperature;89.11%
With sodium hydroxide In ethanol Reflux; Inert atmosphere;70%
With ethanol; sodium hydroxide Inert atmosphere; Reflux;70%
(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate
1016214-10-0

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate Product distribution / selectivity;88%
With sodium carbonate In water; ethyl acetate80%
With sodium hydroxide; water In isopropyl alcohol Product distribution / selectivity;
1-[benzyl[2(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)propan-2-ol
72955-94-3

1-[benzyl[2(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)propan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In water; ethyl acetate at 20 - 50℃; for 8h;84%
With hydrogen; palladium 10% on activated carbon In methanol at 70℃; under 2942.29 - 4413.43 Torr;76.7%
With hydrogen; 5%-palladium/activated carbon In ethyl acetate at 60 - 70℃; under 2574.5 - 3310.08 Torr; for 10h;
1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol
143412-40-2, 143412-41-3, 72955-96-5

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol

1-(2-chloroethoxy)-2-methoxybenzene
53815-60-4

1-(2-chloroethoxy)-2-methoxybenzene

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With potassium carbonate In toluene at 80 - 85℃;83%
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

4-(2,3-epoxypropoxy)carbazole
51997-51-4

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
In isopropyl alcohol for 5h; Inert atmosphere; Reflux;81%
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 80 - 85℃;36.26%
With sulfuric acid; potassium carbonate In isopropyl alcohol at 80℃; for 6h;
4-[2-(tert-butyldiphenylsilyloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propyloxy]carbazole

4-[2-(tert-butyldiphenylsilyloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propyloxy]carbazole

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30 - 40℃; for 17h;67%
(+/-) 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethyl]amino-2-propanol oxalate
72956-09-3

(+/-) 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethyl]amino-2-propanol oxalate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With ammonia In dichloromethane; water at 20℃; for 1h; pH=9.0 - 9.3;63.2%
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

4-(2,3-epoxypropoxy)carbazole
51997-51-4

4-(2,3-epoxypropoxy)carbazole

A

C39H39N3O6
918903-20-5

C39H39N3O6

B

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
In dimethyl sulfoxide at 68 - 72℃; for 18 - 20h;A n/a
B 58%
...Expand
2-[(2-methoxy)phenoxy]ethylamine hydrochloride
64464-07-9

2-[(2-methoxy)phenoxy]ethylamine hydrochloride

4-(2,3-epoxypropoxy)carbazole
51997-51-4

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Stage #1: 2-[(2-methoxy)phenoxy]ethylamine hydrochloride With sodium hydroxide In water at 20℃; pH=9 - 9.5;
Stage #2: 4-(2,3-epoxypropoxy)carbazole In water at 80 - 85℃; for 0.75 - 1h; Product distribution / selectivity;		45.99%
Stage #1: 2-[(2-methoxy)phenoxy]ethylamine hydrochloride With sodium hydroxide In water; isopropyl alcohol at 20℃; pH=9 - 9.5;
Stage #2: 4-(2,3-epoxypropoxy)carbazole In water; isopropyl alcohol for 4 - 5h; Product distribution / selectivity; Heating / reflux;		43.05%
With potassium carbonate In i-Amyl alcohol at 80 - 85℃; for 7h;41%
With calcium carbonate In isopropyl alcohol at 80℃; for 4h;
4-(2,3-epoxypropoxy)carbazole
51997-51-4

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Stage #1: 2-[(2-methoxy)phenoxy]ethylamine hydrochloride With potassium carbonate In isopropyl alcohol at 35℃; for 0.25h;
Stage #2: 4-(2,3-epoxypropoxy)carbazole In isopropyl alcohol at 83℃; for 5h;		45%
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 140 °C
2: methylamine / water / 2 h / 80 °C
3: potassium carbonate / toluene / 80 - 85 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / water; methanol / 0 - 30 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 90 - 95 °C
3: methylamine / water / 2 h / 80 °C
4: dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride / toluene / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: 4-methoxypyridine N-oxide; sodium sulfate / dichloromethane / 60 h / 20 °C
2: potassium carbonate / toluene / 60 h / Reflux
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 30 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: water; hydrogen bromide / isopropyl alcohol / 25 - 60 °C
2: triethylamine / isopropyl alcohol / 60 °C
View Scheme
(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate
787598-91-8

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium hydroxide; water In isopropyl alcohol Product distribution / selectivity;
(±)-1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol sulfate
374779-43-8

(±)-1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol sulfate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate Product distribution / selectivity;
C27H34N2O4Si
1187921-88-5

C27H34N2O4Si

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Stage #1: C27H34N2O4Si With phosphoric acid; water In ethyl acetate at 20 - 25℃;
Stage #2: With ammonia In water; ethyl acetate pH=~ 9.5; Product distribution / selectivity;
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

1-(9H-carbazol-4-yloxy)-3-bromopropan-2-ol
1187921-94-3

1-(9H-carbazol-4-yloxy)-3-bromopropan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 60℃; Product distribution / selectivity;
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol
1187921-93-2

1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
With potassium carbonate In toluene at 80 - 85℃; for 13h; Product distribution / selectivity;
9H-carbazol-4-ol
52602-39-8

9H-carbazol-4-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; dimethyl sulfoxide / 12 h / 25 - 45 °C
2: 1,2-dimethoxyethane; ethyl acetate
View Scheme
Multi-step reaction with 5 steps
1.1: pyridine / isopropyl alcohol / 0.17 h / Inert atmosphere
1.2: 16 h / 15 - 20 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 12 h / 5 - 20 °C / Inert atmosphere
3.1: dmap / N,N-dimethyl-formamide / 15 - 30 °C / Inert atmosphere
4.1: 100 - 110 °C / Inert atmosphere
5.1: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: pyridine / isopropyl alcohol / 0.17 h / Inert atmosphere
1.2: 16 h / 15 - 20 °C / Inert atmosphere
2.1: dichloromethane / 4 h / 0 °C / Inert atmosphere
3.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere
4.1: 100 - 110 °C / Inert atmosphere
5.1: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol
1187921-93-2

1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / dichloromethane / 12 h / 5 - 20 °C / Inert atmosphere
2: dmap / N,N-dimethyl-formamide / 15 - 30 °C / Inert atmosphere
3: 100 - 110 °C / Inert atmosphere
4: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 4 steps
1: dichloromethane / 4 h / 0 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere
3: 100 - 110 °C / Inert atmosphere
4: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 90 - 95 °C
2: methylamine / water / 2 h / 80 °C
3: dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride / toluene / 5 h / Reflux
View Scheme
3-((9H-carbazol-4-yloxy)methyl)-3-chloropropane-2-yl phenyl carbonate
1392322-33-6

3-((9H-carbazol-4-yloxy)methyl)-3-chloropropane-2-yl phenyl carbonate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap / N,N-dimethyl-formamide / 15 - 30 °C / Inert atmosphere
2: 100 - 110 °C / Inert atmosphere
3: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol chloroformate

1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol chloroformate

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere
2: 100 - 110 °C / Inert atmosphere
3: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap / N,N-dimethyl-formamide / 15 - 30 °C / Inert atmosphere
2: 100 - 110 °C / Inert atmosphere
3: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere
2: 100 - 110 °C / Inert atmosphere
3: ethanol; sodium hydroxide / Inert atmosphere; Reflux
View Scheme
5-((9H-carbazol-4-yloxy)methyl)-oxazolidin-2-one
1218777-33-3

5-((9H-carbazol-4-yloxy)methyl)-oxazolidin-2-one

1-(2-chloroethoxy)-2-methoxybenzene
53815-60-4

1-(2-chloroethoxy)-2-methoxybenzene

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 25 h / 25 - 100 °C / Inert atmosphere
2: sodium hydroxide / ethanol / 12 h / Reflux; Inert atmosphere
View Scheme
1-(9H-carbazol-4-yloxy)-3-(benzhydrylamino)propan-2-ol
1392100-68-3

1-(9H-carbazol-4-yloxy)-3-(benzhydrylamino)propan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium 10% on activated carbon / methanol / 6 h / 3102.97 - 3620.13 Torr / Inert atmosphere
2: 0 °C / Reflux; basic condition; Inert atmosphere
3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 25 h / 25 - 100 °C / Inert atmosphere
4: sodium hydroxide / ethanol / 12 h / Reflux; Inert atmosphere
View Scheme
1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol
143412-40-2, 143412-41-3, 72955-96-5

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0 °C / Reflux; basic condition; Inert atmosphere
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 25 h / 25 - 100 °C / Inert atmosphere
3: sodium hydroxide / ethanol / 12 h / Reflux; Inert atmosphere
View Scheme
5-((9H-carbazol-4-yloxy)methyl)-oxazolidin-2-one
1218777-33-3

5-((9H-carbazol-4-yloxy)methyl)-oxazolidin-2-one

1-(2-iodoethoxy)-2-methoxybenzene
1187921-84-1

1-(2-iodoethoxy)-2-methoxybenzene

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 36 h / 100 °C
2: water; sodium hydroxide / ethanol / 12 h / Reflux
View Scheme
2-methoxy-phenol
90-05-1

2-methoxy-phenol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrabutylammomium bromide; sodium hydroxide / water / 5 h / 80 °C
2: sodium iodide / acetone / 48 h / Reflux
3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 36 h / 100 °C
4: water; sodium hydroxide / ethanol / 12 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide; tetrabutylammomium bromide / water / 0.25 h / 30 °C
1.2: 20 - 70 °C
2.1: sodium hydroxide / toluene / 0.17 h / 25 - 30 °C
2.2: 25 - 30 °C
3.1: dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride / toluene / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide; sodium hydroxide / 16 h / Reflux
2: water; sodium hydroxide / 13 h / 130 °C
3: ethyl acetate / 24 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: tetrabutylammomium bromide; sodium hydroxide / 16 h / Reflux
2: tetrabutylammomium bromide / 180 - 185 °C
3: water; potassium hydroxide / 13 h / 130 °C
4: ethyl acetate / 24 h / Reflux
View Scheme
1-(2-chloroethoxy)-2-methoxybenzene
53815-60-4

1-(2-chloroethoxy)-2-methoxybenzene

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium iodide / acetone / 48 h / Reflux
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 36 h / 100 °C
3: water; sodium hydroxide / ethanol / 12 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: water; sodium hydroxide / 13 h / 130 °C
2: ethyl acetate / 24 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide / 180 - 185 °C
2: water; potassium hydroxide / 13 h / 130 °C
3: ethyl acetate / 24 h / Reflux
View Scheme
sodium salt of 9H-carbazol-4-ol
1207276-96-7

sodium salt of 9H-carbazol-4-ol

carvedilol
72956-09-3

carvedilol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 48 h / 100 °C
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 36 h / 100 °C
3: water; sodium hydroxide / ethanol / 12 h / Reflux
View Scheme
carvedilol
72956-09-3

carvedilol

C24H22(2)H4N2O4

C24H22(2)H4N2O4

Conditions
ConditionsYield
With deuterium In tetrahydrofuran under 1500.15 Torr; for 24h; Glovebox; Heating;99%
carvedilol
72956-09-3

carvedilol

1-(carbazol-4-yloxy)-3-[[2-(O-methoxyphenoxy)ethyl]amino]-2-propanol dihydrogen phosphate

1-(carbazol-4-yloxy)-3-[[2-(O-methoxyphenoxy)ethyl]amino]-2-propanol dihydrogen phosphate

Conditions
ConditionsYield
With phosphoric acid In acetonitrile at 20℃; for 0.5h; Product distribution / selectivity;98%
With phosphoric acid In acetone Product distribution / selectivity;98%
With phosphoric acid In methanol Product distribution / selectivity;98%
carvedilol
72956-09-3

carvedilol

1-(9H-carbazole-4-oxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanolphosphate
374779-45-0

1-(9H-carbazole-4-oxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanolphosphate

Conditions
ConditionsYield
With phosphoric acid In water; acetonitrile at 20 - 70℃; Product distribution / selectivity;97%
With phosphoric acid In water; N,N-dimethyl-formamide; isopropyl alcohol at 20℃; Product distribution / selectivity;96%
With phosphorus pentoxide In water; acetone at 0 - 45℃; Product distribution / selectivity;95%
carvedilol
72956-09-3

carvedilol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C29H34N2O6

C29H34N2O6

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h;96%
carvedilol
72956-09-3

carvedilol

carvedilol dihydrogen phosphate hemihydrate

carvedilol dihydrogen phosphate hemihydrate

Conditions
ConditionsYield
With phosphorus pentoxide In water; acetone at 0 - 45℃; for 1h; Product distribution / selectivity;95%
With hydrogenchloride; dipotassium hydrogenphosphate In water; acetone at 0 - 45℃; for 1h; pH=4.5 - 5; Product distribution / selectivity;94.49%
With PPA In water; acetone at 0 - 45℃; for 1h; Product distribution / selectivity;93.3%
carvedilol
72956-09-3

carvedilol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one
180987-80-8

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 5h;93%
With triethylamine In dichloromethane at 20℃;
carvedilol
72956-09-3

carvedilol

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol sulfate salt

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol sulfate salt

Conditions
ConditionsYield
With sulfuric acid In ethanol; water92.1%
With sulfuric acid In water; acetone at 17 - 35℃; for 10 - 24h;
carvedilol
72956-09-3

carvedilol

2'-(((2S,3R,4S,5S)-3,4,5-triacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yloxy)carbonylamino)biphenyl-2-carboxylic acid
320401-51-2

2'-(((2S,3R,4S,5S)-3,4,5-triacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yloxy)carbonylamino)biphenyl-2-carboxylic acid

A

6(5H)-phenanthridinone
1015-89-0

6(5H)-phenanthridinone

B

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{[3-(9H-carbazol-4-yloxy)-2-hydroxy-propyl]-[2-(2-methoxy-phenoxy)-ethyl]-carbamoyloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{[3-(9H-carbazol-4-yloxy)-2-hydroxy-propyl]-[2-(2-methoxy-phenoxy)-ethyl]-carbamoyloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethaneA n/a
B 92%
...Expand
carvedilol
72956-09-3

carvedilol

(±)-1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol sulfate
374779-43-8

(±)-1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol sulfate

Conditions
ConditionsYield
With sulfuric acid In ethanol; water89.6%
With sulfuric acid In dichloromethane; water pH=4.0 - 4.5;
With sulfuric acid In water; acetone at 17 - 35℃; for 10 - 24h;
carvedilol
72956-09-3

carvedilol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

C26H26N2O5

C26H26N2O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 95℃; for 18h;77%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 95℃; for 18h; Product distribution / selectivity;75%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 95℃;
carvedilol
72956-09-3

carvedilol

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

C31H29N3O4

C31H29N3O4

Conditions
ConditionsYield
Stage #1: carvedilol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;		71%
carvedilol
72956-09-3

carvedilol

trifluoroacetic acid
76-05-1

trifluoroacetic acid

8-chlorocarvedilol

8-chlorocarvedilol

Conditions
ConditionsYield
With glucose dehydrogenase; alpha-D-glucopyranose; maltose binding protein-RebF; RebH variant 4-V; nicotinamide adenine dinucleotide; flavin adenine dinucleotide; sodium chloride In methanol at 25℃; for 72h; pH=7.4; Enzymatic reaction;69%
carvedilol
72956-09-3

carvedilol

citric acid
77-92-9

citric acid

carvedilol monocitrate monohydrate
623113-70-2

carvedilol monocitrate monohydrate

Conditions
ConditionsYield
With water In acetone at 20 - 40℃; Product distribution / selectivity;67%
With water In acetone at 20 - 40℃; for 24 - 48h; Product distribution / selectivity;67%
With water
With water Product distribution / selectivity;
carvedilol
72956-09-3

carvedilol

Diethyl carbonate
105-58-8

Diethyl carbonate

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one
180987-80-8

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: carvedilol In methanol
Stage #2: With methanol; sodium In methanol
Stage #3: Diethyl carbonate In methanol for 12h; Product distribution / selectivity; Heating / reflux;		65%
carvedilol
72956-09-3

carvedilol

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one
180987-80-8

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1h; Sealed tube;61%
carvedilol
72956-09-3

carvedilol

MANDELIC ACID
611-71-2, 611-72-3, 17199-29-0, 90-64-2

MANDELIC ACID

carvedilol mandelate
852995-78-9

carvedilol mandelate

Conditions
ConditionsYield
In methanol; water; acetone at 17 - 35℃; for 10 - 24h;54.5%
In methanol; water; acetone at 17 - 35℃; for 10 - 24h;54.5%
carvedilol
72956-09-3

carvedilol

methyl iodide
74-88-4

methyl iodide

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]methylamino}-2-propanol
72956-35-5

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]methylamino}-2-propanol

Conditions
ConditionsYield
Stage #1: carvedilol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 4h;		54%
With sodium hydride In tetrahydrofuran at 20℃; for 4h;54%
In tetrahydrofuran at 20℃;
carvedilol
72956-09-3

carvedilol

methyl iodide
74-88-4

methyl iodide

C26H30N2O4

C26H30N2O4

Conditions
ConditionsYield
Stage #1: carvedilol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 4h;		49%

Carvedilol Chemical Properties

Structure of Carvedilol (CAS NO.72956-09-3): 

IUPAC Name: 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol 
Empirical Formula: C24H26N2O4
Molecular Weight: 406.4742g/mol
Index of Refraction: 1.657
Molar Refractivity: 119.59 cm3
Molar Volume: 325.1 cm3
Polarizability: 47.41×10-24cm3
Surface Tension: 53.9 dyne/cm
Density: 1.25 g/cm3
Flash Point: 350.1 °C
Enthalpy of Vaporization: 101.39 kJ/mol 
Melting Point: 113-117°C
Boiling Point: 655.2 °C at 760 mmHg
Vapour Pressure: 4.63E-18 mmHg at 25°C 
Product Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;API's;Adrenoceptor 
Canonical SMILES: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O
InChI: InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3
InChIKey: OGHNVEJMJSYVRP-UHFFFAOYSA-N

Carvedilol Uses

 Carvedilol (CAS NO.72956-09-3) is a beta blocker and an alpha blocker indicated in the treatment of mild to moderate congestive heart failure (CHF).

Carvedilol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
mouse LD50 intraperitoneal 364mg/kg (364mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse LD50 intravenous 27mg/kg (27mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse LDLo oral 8gm/kg (8000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
rat LD50 intraperitoneal 769mg/kg (769mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat LD50 intravenous 25mg/kg (25mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat LDLo oral 8gm/kg (8000mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.

Carvedilol Safety Profile

Hazard Codes of Carvedilol (CAS NO.72956-09-3): DangerousN,HarmfulXn
Risk Statements: 51/53-36/37/38-20/21/22
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 61-36-26
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 3077 9/PG 3
RTECS: UA8670000

Carvedilol Specification

 Carvedilol , its cas register number is 72956-09-3. It also can be called (+-)-1-(Carbazol-4-yloxy)-3-((2-(o-
methoxyphenoxy)ethyl)amino)-2-propanol ; (+-)-1-Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol ;
 2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)- ; BM 14190 ; Carvedilolum ; Coreg ;
 DQ 2466 ; HSDB 7044 ; SKF 105517 ; UNII-0K47UL67F2 . Carvedilol (CAS NO.72956-09-3) is a colourless crystalline solid. Side effects of carvedilol were observed to include nightmares,sleep disturbances and anxiety and panic attacks. This is based on a single case report of a patient already diagnosed with anxiety disorder and using the drug improperly before bedtime at elevated doses.

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