alpha-Hydroxymetoprolol

Base Information

• Chemical Name: alpha-Hydroxymetoprolol
• CAS No.: 56392-16-6
• Molecular Formula: C15H25NO4
• Molecular Weight: 283.368
• UNII: C19D0413EL
• DSSTox Substance ID: DTXSID201024019
• Nikkaji Number: J394.877C
• Wikidata: Q27275053
• Metabolomics Workbench ID: 71610
• ChEMBL ID: CHEMBL3544701
• Mol file: 56392-16-6.mol

Synonyms:alpha-hydroxymetoprolol;H 119-66;H119-66

Chemical Property of alpha-Hydroxymetoprolol

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 65-67 ºC
• Boiling Point: 437.6 ºC at 760 mmHg
• Flash Point: 218.4 ºC
• PSA: 70.95000
• Density: 1.102 g/cm³
• LogP: 1.49500
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 283.17835828
• Heavy Atom Count: 20
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

α-Hydroxy Metoprolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)C(COC)O)O
• Uses: A metabolite of Metoprolol A metabolite of Metoprolol.

Technology Process of alpha-Hydroxymetoprolol

There total 8 articles about alpha-Hydroxymetoprolol 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: 95.0%

3-<4-(methylacetyl)phenoxy>-1-(isopropylamino)-2-propanol (110458-45-2,73723-85-0) → alpha-Hydroxymetoprolol (56392-16-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 90h;

DOI:10.1021/jm00396a009

Reference yield:

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → alpha-Hydroxymetoprolol (56392-16-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / methanol / 0.5 h / Heating

2: 80 percent / NaOH / dimethylformamide / 2 h / Heating

3: 67 percent / aq. HCl / acetone / 2 h / Heating

4: 1.) TsCl, 2.) NaH / 1.) pyridine, 0 deg C, 4 d, 2.) reflux, 90 min

5: 40 percent / NH₄Cl / 24 h

6: 95 percent / NaBH₄ / methanol / 90 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium hydride; ammonium chloride; p-toluenesulfonyl chloride; In methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00396a009

Reference yield:

alpha-methoxy-4-hydroxyacetophenone (32136-81-5) → alpha-Hydroxymetoprolol (56392-16-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaOH / dimethylformamide / 2 h / Heating

2: 67 percent / aq. HCl / acetone / 2 h / Heating

3: 1.) TsCl, 2.) NaH / 1.) pyridine, 0 deg C, 4 d, 2.) reflux, 90 min

4: 40 percent / NH₄Cl / 24 h

5: 95 percent / NaBH₄ / methanol / 90 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium hydride; ammonium chloride; p-toluenesulfonyl chloride; In methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00396a009

upstream raw materials:

3-<4-(methylacetyl)phenoxy>-1-(isopropylamino)-2-propanol

(RS)-metoprolol

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone

alpha-methoxy-4-hydroxyacetophenone

Refernces

• 1、 Bapiro, Tashinga E.,Hasler, Julia A.,Ridderstroem, Marianne,Masimirembwa, Collen M. "The molecular and enzyme kinetic basis for the diminished activity of the cytochrome P450 2D6.17 (CYP2D6.17) variant: Potential implications for CYP2D6 phenotyping studies and the clinical use of CYP2D6 substrate drugs in some African populations". . p. 1387 - 1398. Retrieved 2007/10/03.