Propranolol

Base Information

• Chemical Name: Propranolol
• CAS No.: 525-66-6
• Deprecated CAS: 13013-17-7
• Molecular Formula: C16H21 N O2
• Molecular Weight: 259.348
• Hs Code.: 2922210000
• European Community (EC) Number: 208-378-0
• UNII: 9Y8NXQ24VQ
• DSSTox Substance ID: DTXSID6023525
• Nikkaji Number: J6.653B
• Wikipedia: Propranolol
• Wikidata: Q423364
• NCI Thesaurus Code: C62073
• RXCUI: 8787
• Pharos Ligand ID: ABUFMXMUC39Q
• Metabolomics Workbench ID: 129953
• ChEMBL ID: CHEMBL27
• Mol file: 525-66-6.mol

Synonyms:Anaprilin;Anapriline;Avlocardyl;AY 20694;AY-20694;AY20694;Betadren;Dexpropranolol;Dociton;Hydrochloride, Propranolol;Inderal;Obsidan;Obzidan;Propanolol;Propranolol;Propranolol Hydrochloride;Rexigen

Chemical Property of Propranolol

Chemical Property:

• Appearance/Colour: White, odorless crystalline powder.
• Melting Point: 163-164 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 434.9 °C at 760 mmHg
• PKA: 13.84±0.20(Predicted)
• Flash Point: 216.8 °C
• PSA: 41.49000
• Density: 1.093 g/cm³
• LogP: 2.96840
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 80.99mg/L(25 oC)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

Propranolol-d7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Highly toxic.
• Hazard Codes: Highly toxic.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
• Recent ClinicalTrials: Mismatch vs. Standard Intervention During Memory Reconsolidation Blockade With Propranolol: Effect on Psychophysiological Reactivity During Traumatic Imagery
• Recent EU Clinical Trials: An open label phase 2 study on propranolol and pembrolizumab in advanced Angiosarcoma and Undifferentiated Pleomorphic Sarcoma – a Scandinavian Sarcoma Group collaboration
• Recent NIPH Clinical Trials: An Open-Label Single-Arm Clinical Trial to Evaluate the Efficacy of Propranolol Ointment in Infantile Hemangioma
• Description: Propranolol was responsible for sensitisation of workers in drug synthesis. In one case, epichlorhydrin was used for the production of both propranolol and oxprenolol.
• Uses: Cardiac depressant (anti-arrhythmic); anti-adrenergic (β-receptor).

Technology Process of Propranolol

There total 112 articles about Propranolol 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%

(S)-(+)-1-chloro-2-acetoxy-3-(1-naphthyloxy)propane (132076-77-8) + isopropylamine (75-31-0) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2004.05.084

Reference yield: 93.0%

C26H41NO4Si (228704-16-3) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo990272o

Reference yield: 90.0%

[(R)-2-Benzyloxy-3-(naphthalen-1-yloxy)-propyl]-isopropyl-amine → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h; Ambient temperature;

DOI:10.1016/0957-4166(96)00337-0

upstream raw materials:

1-chloro-3-(1-naphthoxy)-2-propanol

isopropylamine

3-isopropyl-5-<(nphthyloxy)methyl>oxazolidin-2-one

3-(1-naphthyloxy)-1,2-epoxypropane

Downstream raw materials:

1-[2-Hydroxy-3-(naphthalen-1-yloxy)-propyl]-1-isopropyl-3-phenyl-urea

N-[2-acetyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide

R-(+)-propranolol

S-(-)-propranolol

Refernces

• 1、 Triana, Maria T.,Reyes, Andrea C.,Jimenez-Kairuz, Alvaro F.,Manzo, Ruben H.,Martinez, Fleming. "Solution and mixing thermodynamics of propranolol and atenolol in aqueous media". . p. 73 - 81. Retrieved 2009.
• 2、 Burns. "". . p. 45,47. Retrieved 1970.
• 3、 -. "Preparation method of propranolol". Paragraph 0018-0020. . Retrieved 2021/06/23.
• 4、 Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap. "Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition". . . Retrieved 2021/07/22.