4-Hydroxypropranolol

Base Information

• Chemical Name: 4-Hydroxypropranolol
• CAS No.: 10476-53-6
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.348
• UNII: 2449QP4SVP
• DSSTox Substance ID: DTXSID70893062
• Nikkaji Number: J275.280H
• Wikidata: Q27253809
• ChEMBL ID: CHEMBL1137
• Mol file: 10476-53-6.mol

Synonyms:1-(4-hydroxynaphth-1-yloxy)-3-isopropylamino-2- propanol;4-hydroxypropranolol;4-hydroxypropranolol hydrochloride;4-hydroxypropranolol hydrochloride, (+-)-isomer;4-hydroxypropranolol, (+-)-isomer;4-hydroxypropranolol, (R)-isomer;4-hydroxypropranolol, (S)-isomer

Chemical Property of 4-Hydroxypropranolol

Chemical Property:

• Melting Point: 167-169°C
• Refractive Index: 1.604
• Boiling Point: 487.5°Cat760mmHg
• Flash Point: 248.6°C
• PSA: 61.72000
• Density: 1.168g/cm³
• LogP: 3.47600
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 275.15214353
• Heavy Atom Count: 20
• Complexity: 285

Purity/Quality:

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

(+/-)-4-HYDROXY PROPRANOLOL HYDROCHLORIDE 95.00% ^*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(C2=CC=CC=C21)O)O
• Uses: 4-Hydroxypropranolol is a metabolite of Propranolol (P831800), a β?adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II). A metabolite of Propranolol

Technology Process of 4-Hydroxypropranolol

There total 9 articles about 4-Hydroxypropranolol 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:

4-Methoxypropranolol (18507-09-0,437999-45-6,437999-44-5) → 4-hydroxypropranolol (10476-53-6,69499-28-1,76792-96-6,76792-97-7)

Guidance literature:

With pyridine hydrochloride; at 155 - 180 ℃; for 1h;

DOI:10.1021/jm00135a014

Reference yield:

3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9) → 4-hydroxypropranolol (10476-53-6,69499-28-1,76792-96-6,76792-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.1 percent / toluene / 18 h / 80 °C / with naphthalene ring-<14C>-labeled educt

2: glucose-6-phosphate; glucose-6-phosphate dehydrogenase; NADP / aq. phosphate buffer / 1.25 h / 37 °C / pH 7.4 / Enzymatic reaction; with naphthalene ring-<14C>-labeled educt and β-naphthoflavone-induced microsomes

With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; NADP; In phosphate buffer; toluene;

DOI:10.1021/tx960165e

Reference yield:

α-naphthol (90-15-3) → 4-hydroxypropranolol (10476-53-6,69499-28-1,76792-96-6,76792-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / K₂CO₃ / dimethylformamide / 24 h / 60 °C / with maphthalene ring-<14C>-labeled educt

2: 84.1 percent / toluene / 18 h / 80 °C / with naphthalene ring-<14C>-labeled educt

3: glucose-6-phosphate; glucose-6-phosphate dehydrogenase; NADP / aq. phosphate buffer / 1.25 h / 37 °C / pH 7.4 / Enzymatic reaction; with naphthalene ring-<14C>-labeled educt and β-naphthoflavone-induced microsomes

With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; NADP; potassium carbonate; In phosphate buffer; N,N-dimethyl-formamide; toluene;

DOI:10.1021/tx960165e

upstream raw materials:

(+/-)-4-Methoxypropranolol hydrochloride

4-Methoxypropranolol

Inderal

propranolol

Downstream raw materials:

[1,4]naphthoquinone