Oxprenolol

Base Information

• Chemical Name: Oxprenolol
• CAS No.: 6452-71-7
• Deprecated CAS: 22972-98-1,71186-75-9
• Molecular Formula: C15H23 N O3
• Molecular Weight: 265.353
• European Community (EC) Number: 229-257-9,245-359-6,245-357-5
• UNII: 519MXN9YZR
• DSSTox Substance ID: DTXSID1043835
• Nikkaji Number: J8.410G,J318.375K
• Wikipedia: Oxprenolol
• Wikidata: Q425963
• NCI Thesaurus Code: C66276
• Pharos Ligand ID: UHUXQ8RS39PB
• Metabolomics Workbench ID: 43574
• ChEMBL ID: CHEMBL546
• Mol file: 6452-71-7.mol

Synonyms:Coretal;Hydrochloride, Oxprenolol;Koretal;Oxprenolol;Oxprenolol Hydrochloride;Slow Trasicor;Tevacor;Trasicor;Trasicor, Slow

Chemical Property of Oxprenolol

Chemical Property:

• Melting Point: 78-80°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 408.57°C (rough estimate)
• PSA: 50.72000
• Density: 1.0479 (rough estimate)
• LogP: 2.38000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 265.16779360
• Heavy Atom Count: 19
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

OXPRENOLOL-D7 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CC(C)NCC(COC1=CC=CC=C1OCC=C)O
• Description: Oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in the division for drug synthesis. Epichlorhydrin was also used for the production of both propranolol and oxprenolol.
• Uses: Vasodilator(coronary).
• Therapeutic Function: Antiarrhythmic

Technology Process of Oxprenolol

There total 36 articles about Oxprenolol 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:

decanoic acid 2-(2-allyloxy-phenoxy)-1-(isopropylamino-methyl)-ethyl ester → 1-decanoic acid (334-48-5) + oxprenolol (6452-71-7)

Guidance literature:

In water; at 37 ℃; pH=0.4; Further Variations:; pH-values; Kinetics;

Reference yield:

2-allyloxyphenol (1126-20-1) → oxprenolol (6452-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0 °C

1.2: 80 percent / dimethylformamide

2.1: propan-2-ol / Heating

With sodium hydride; In N,N-dimethyl-formamide; isopropyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Ring cleavage;

DOI:10.1016/S0957-4166(00)00254-8

Reference yield:

O-propionyloxprenolol (144106-10-5) → propionic acid (802294-64-0,79-09-4) + oxprenolol (6452-71-7)

Guidance literature:

With borate buffer; In methanol; water; at 37 ℃; pH=9.0; Further Variations:; pH-values; Reagents; Temperatures; Kinetics;

DOI:10.1021/js970112x

upstream raw materials:

3-(o-Allyloxyphenoxy)-2-hydroxy-1-chlorpropan

isopropylamine

BA 42154

allyl bromide

Downstream raw materials:

1-[2-(allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol

(-)-Oxprenolol

2-(2-allyloxyphenoxy)acetic acid

(R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene

Refernces

• 1、 Gogaladze, Khatuna,Chankvetadze, Lali,Tsintsadze, Maia,Farkas, Tivadar,Chankvetadze, Bezhan. "Effect of basic and acidic additives on the separation of some basic drug enantiomers on polysaccharide-based chiral columns with acetonitrile as mobile phase". . p. 228 - 234. Retrieved 2015/03/18.
• 2、 -. "S-ENANTIOMERICALLY ENRICHED COMPOSITIONS OF BETA BLOCKERS FOR TREATING AMYOTROPHIC LATERAL SCLEROSIS". Paragraph 0147-0149. . Retrieved 2014/09/29.