17216-10-3

Basic information

• Product Name: 1,3-Bis(1-naphthalenyloxy)-2-propanol
• Synonyms: 1,3-Bis(1-naphthalenyloxy)-2-propanol;Propranolol iMpurity C, bis-ether derivative;1,3-Bis(1-naphthoxy)-2-propanol;1,3-Bis(naphthalen-1-yloxy)propan-2-ol;1,3-bis(naphthalen-1-yloxy)propan-2-;Propranolol Impurity C;Propranolol EP impurity C
• CAS NO: 17216-10-3
• Molecular Formula: C₂₃H₂₀O₃
• Molecular Weight: 344.4031
• EINECS: 935-765-8
• Product Categories: Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 17216-10-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 77-78℃
• Boiling Point: 566.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.225±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.27±0.20(Predicted)
• CAS DataBase Reference: 1,3-Bis(1-naphthalenyloxy)-2-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(1-naphthalenyloxy)-2-propanol(17216-10-3)
• EPA Substance Registry System: 1,3-Bis(1-naphthalenyloxy)-2-propanol(17216-10-3)

Safety Data

• Hazardous Substances Data: 17216-10-3(Hazardous Substances Data)

Usage

Description

1,3-Bis(1-naphthalenyloxy)-2-propanol is an organic compound that is characterized by its molecular structure featuring two naphthalenyloxy groups attached to the first and third carbon atoms of a propanol molecule. 1,3-Bis(1-naphthalenyloxy)-2-propanol is known for its unique properties and potential applications in various industries.

Uses

1. Used in Pharmaceutical Industry:
1,3-Bis(1-naphthalenyloxy)-2-propanol is used as an impurity in the production of Propranolol (P831800), which is a β-adrenergic blocker. The application reason for this compound is to serve as a crucial component in the synthesis process of Propranolol, a medication used as an antihypertensive and anti-anginal agent. This indicates its importance in the development and manufacturing of medications that help manage high blood pressure and alleviate chest pain caused by inadequate blood supply to the heart.

Upstream product

• 90-15-3 α-naphthol 
• 106-89-8 epichlorohydrin 
• 109-01-3 1-methyl-piperazine 
• 21230-07-9 N-isopropyl-p-toluenesulfonamide 
• 90-43-7 2-Phenylphenol 
• 31252-42-3 4-benzylpyperidine 
• 50541-93-0 4-amino-1-benzylpiperidine 
• 822-98-0 (1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine 
• 104-94-9 4-methoxy-aniline 
• 75-31-0 isopropylamine 
• 100-46-9 benzylamine 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 

Downstream Products

• 1473412-15-5 4-{2-(1-naphthyloxy)-1-[(1-naphthyloxy)methyl]ethoxy}phthalonitrile 

Relevant articles and documents

Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines

We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 μM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines (4m and 4o) showed excellent profiles in the treatment of L. amazonensis-infected macrophages, reducing the parasite burden by more than 95% in tested concentrations.

Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor

Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of d-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 μM and 50 μM, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization.

Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols

Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-π interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.