20133-93-1

Basic information

• Product Name: 1-chloro-3-(1-naphthyloxy)propan-2-ol
• Synonyms: 1-chloro-3-(1-naphthyloxy)propan-2-ol;1-(Naphth-1-yloxy)-3-chloro-propan-2-ol;1-(1-Naphtyloxy)-3-chloro-2-propanol;1-Chloro-3-(1-naphtyloxy)-2-propanol;1-Chloro-3-(1-naphtyloxy)propane-2-ol;3-Chloro-1-(1-naphtyloxy)-2-propanol
• CAS NO: 20133-93-1
• Molecular Formula: C₁₃H₁₃ClO₂
• Molecular Weight: 236.69412
• EINECS: 243-538-3
• Mol File: 20133-93-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 413.1 °C at 760 mmHg
• Flash Point: 203.6 °C
• Appearance: /
• Density: 1.246 g/cm³
• Vapor Pressure: 1.46E-07mmHg at 25°C
• Refractive Index: 1.616
• PKA: 13.07±0.20(Predicted)
• CAS DataBase Reference: 1-chloro-3-(1-naphthyloxy)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-3-(1-naphthyloxy)propan-2-ol(20133-93-1)
• EPA Substance Registry System: 1-chloro-3-(1-naphthyloxy)propan-2-ol(20133-93-1)

Safety Data

• Hazardous Substances Data: 20133-93-1(Hazardous Substances Data)

Usage

Description

1-Chloro-3-(1-naphthyloxy)propan-2-ol is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical agents. It is characterized by the presence of a chloro group, a naphthyloxy group, and a secondary alcohol functional group, which contribute to its reactivity and potential applications in the chemical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
1-Chloro-3-(1-naphthyloxy)propan-2-ol is used as a key intermediate in the synthesis of β-adrenergic blocking agents and antihypertensive drugs, such as propranolol and nadoxolol. Its unique structural features enable the development of these medications, which are crucial for treating cardiovascular conditions like hypertension and angina.
Used in Enzymatic Kinetic Resolution:
1-Chloro-3-(1-naphthyloxy)propan-2-ol is also utilized in the kinetic resolution studies of its racemic mixture in nonaqueous media. This process employs lipase-catalyzed esterification, which allows for the selective transformation of one enantiomer over the other, leading to the production of enantiomerically pure compounds. This application is significant in the field of asymmetric synthesis and the development of chiral pharmaceuticals.

InChI:InChI=1/C13H13ClO2/c14-8-11(15)9-16-13-7-3-5-10-4-1-2-6-12(10)13/h1-7,11,15H,8-9H2

Upstream product

• 90-15-3 α-naphthol 
• 75-31-0 isopropylamine 
• 106-89-8 epichlorohydrin 
• 20009-25-0 allyl naphthyl ether 
• 30389-33-4 5-hydroxycarbostyril 
• 65910-96-5 1-chloro-3-(1-naphthyloxy)-propan-2-one 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 

Downstream Products

• 36806-78-7 1-[3-(1-Naphthoxy)-2-hydroxyprop-1-yl]-4-benzamidopiperidine 
• 318-98-9 (R)-propranolol hydrochloride 
• 4199-10-4 (S)-(-)-propanolol hydrochloride 
• 128223-61-0 [(S)-2-Benzyloxy-3-(naphthalen-1-yloxy)-propyl]-isopropyl-amine 
• 525-66-6 (R)-propranolol 
• 4199-09-1 (S)-1-isopropylamino-3-(1-naphthyloxy)-2-propanol 
• 18542-14-8 1-benzylamino-3-(naphth-1-yloxy)-2-propanol 
• 4618-24-0 1-butylamino-3-[1]naphthyloxy-propan-2-ol 
• 525-66-6 propranolol 
• 2111-26-4 (+/-)-dimethyl<2-hydroxy-3-(1-naphthyloxy)propyl>amine 
• 36391-23-8 1-(Naphthalen-1-yloxy)-3-phenethylamino-propan-2-ol 
• 2347-27-5 1-(3,4-dimethoxyphenethylamino)-3-(naphthalen-1-yloxy)propan-2-ol 
• 20804-76-6 3-hydroxy-4-(1-naphthyloxy)butanenitrile 

Relevant articles and documents

Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation

Attempts to reproduce eight, putative, enantioselective dibromination and chlorohydroxylation reactions from oft-cited literature studies are described. The reactions were performed with full fidelity to the original report wherever possible. Analysis of the enantiomeric composition was performed by chiral stationary phase HPLC or SFC (CSP-HPLC or CSP-SFC), as opposed to the original report, which used chiral shift reagent NMR spectroscopy. After careful study, the reported levels of enantioselectivity were found to be incorrect. Possible explanations for the false positive results are discussed.

Facile Synthesis of Propranolol and Novel Derivatives

Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride, pyridinium chlorochromate, and n-butyl bromide through esterification, oxidation reduction, and alkylation, respectively. The isolation and purity of compounds were conducted using column chromatography and thin-layer chromatography. Mass spectrometry and 1H-NMR spectroscopy were applied to identify new compounds structure. Propranolol derivatives from 2-chlorobenzoyl chloride (compound 3), 2-fluorobenzoyl chloride (compound 5), and especially acetic anhydride (compound 6) manifested high yields and significantly increased water solubility. Six semisynthetic propranolol derivatives promise to improve antioxidative and biological activities.

Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol

Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantioselectivity under mild reaction conditions.