()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol

Base Information

• Chemical Name: ()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol
• CAS No.: 13013-17-7
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• Mol file: 13013-17-7.mol

Synonyms:(±)-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol;dl-Propanolol;rac-(2R*)-1-Isopropylamino-3-(1-naphthalenyloxy)-2-propanol;rac-Propranolol;(1)-1-(Isopropylamino)-3-(naphthyloxy)propan-2-ol;Einecs 235-867-6

Chemical Property of ()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol

Chemical Property:

• Vapor Pressure: 2.48E-08mmHg at 25°C
• Boiling Point: 434.9°C at 760 mmHg
• Flash Point: 216.8°C
• Density: 1.093g/cm³

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: ()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol (±)-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol, also known as racemic propranolol, is a β-adrenergic receptor blocker that exhibits stereoselective pharmacokinetics and pharmacodynamics. Studies have demonstrated its enantiomeric separation using chiral stationary phases, such as macrocyclic antibiotics (Chirobiotic V) and polysaccharide-based columns (Chiralpak AD-RH, Chiralpak IB), with high predictability in chromatographic behavior. The hydrolysis of its ester prodrugs in rat tissues is stereoselective, with rates dependent on the ester moiety and tissue type, showing preferential hydrolysis of the (R)-isomer in plasma and the (S)-isomer in liver and intestine homogenates. Additionally, dual-flow countercurrent extraction has been employed for enantioseparation, yielding enantiomers with high purity. Analytical methods, including HPLC with fluorescence detection, have been validated for quantifying propranolol enantiomers in biological matrices, supporting its clinical and forensic applications. Molecular modeling further elucidates enantiomer-receptor and enantiomer-chiral selector interactions.

Technology Process of ()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol

There total 58 articles about ()-1-(isopropylamino)-3-(naphthyloxy)propan-2-ol 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:

propranolol

α-naphthol

(R)-3-(1-naphthyloxy)-1,2-propanediol

isopropylamine