(S)-Carvedilol

Base Information

• Chemical Name: (S)-Carvedilol
• CAS No.: 95094-00-1
• Molecular Formula: C₂₄H₂₆N₂O₄
• Molecular Weight: 406.481
• UNII: GW13D96IND
• DSSTox Substance ID: DTXSID50241749
• Nikkaji Number: J415.533E
• Wikidata: Q27279308
• Pharos Ligand ID: BM9T14PVFQGG
• ChEMBL ID: CHEMBL3799125
• Mol file: 95094-00-1.mol

Synonyms:(S)-Carvedilol;95094-00-1;(S)-(-)-Carvedilol;(-)-Carvedilol;Carvedilol, (-)-;(2s)-1-(9h-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol;UNII-GW13D96IND;GW13D96IND;(2S)-1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol;CHEMBL3799125;(2s)-1-(8h-Carbazol-4-Yloxy)-3-[2-(2-Methoxyphenoxy)ethylamino]propan-2-Ol;S-(-)-Carvedilol;S)-(-)-Carvedilol;(S)-BM 14190;SCHEMBL6430026;HY-B0006B;DTXSID50241749;BDBM50167072;AKOS030255655;CS-O-07550;AS-82016;CS-0111827;E78791;Q27279308;(S)-1-(9H-carbazol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol;2-Propanol,1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-,(2S)-;2-PROPANOL, 1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO)-, (2S)-

Chemical Property of (S)-Carvedilol

Chemical Property:

• Appearance/Colour: Colourless crystalline solid
• Vapor Pressure: 4.63E-18mmHg at 25°C
• Melting Point: 114-115 °C
• Refractive Index: 1.657
• Boiling Point: 655.2 °C at 760 mmHg
• PKA: 13.90±0.20(Predicted)
• Flash Point: 350.1 °C
• Density: 1.25 g/cm³
• Storage Temp.: -20°C Freezer
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 406.18925731
• Heavy Atom Count: 30
• Complexity: 508

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(-)-Carvedilol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O
• Isomeric SMILES: COC1=CC=CC=C1OCCNC[C@@H](COC2=CC=CC3=C2C4=CC=CC=C4N3)O
• Uses: (S)-(-)-CARVEDILOL is the optically active isomer of Carvedilol, a nonselective -adrenergic blocker with a1-blocking activity. It is an antihypertensive used in the treatment of congestive heart failure.

Technology Process of (S)-Carvedilol

There total 20 articles about (S)-Carvedilol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

2-(2-methoxy-phenoxy)-ethylamine (1836-62-0) + S-(+)-4-(oxiranylmethoxy)-9H-carbazole (95093-95-1,95093-96-2) → (-)-Carvedilol (95094-00-1,72956-09-3,95093-99-5,107741-96-8)

Guidance literature:

In isopropyl alcohol; for 2h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201604002

Reference yield: 66.0%

(R)-4-(oxiran-2-ylmethoxy)-9H-carbazole (95093-96-2) + 2-(2-methoxy-phenoxy)-ethylamine (1836-62-0) → (+)-Carvedilol (95093-99-5,72956-09-3,95094-00-1,107741-96-8)

Guidance literature:

In isopropyl alcohol; for 4h; Reflux;

DOI:10.1021/acs.jmedchem.9b00349

Reference yield:

carvedilol (72956-09-3) → (+)-Carvedilol (95093-99-5,72956-09-3,95094-00-1,107741-96-8) + (-)-Carvedilol (95094-00-1,72956-09-3,95093-99-5,107741-96-8)

Guidance literature:

With ChiralPak AD column; In methanol; ethanol; hexane; trifluoroacetic acid; Resolution of racemate;

DOI:10.1021/cg100209v

upstream raw materials:

C₂₅H₂₄N₂O₅

carvedilol

(R)-4-(oxiran-2-ylmethoxy)-9H-carbazole

2-(2-methoxy-phenoxy)-ethylamine

Refernces

• 1、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 2、 Fang, Linlin,Yu, Jia,Jiang, Zhen,Guo, Xingjie. "Preparation of a β-cyclodextrin-based open-tubular capillary electrochromatography column and application for enantioseparations of ten basic drugs". . . Retrieved 2016/01/29.