152448-80-1

Basic information

• Product Name: rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone
• Synonyms: rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone;Sertraline 2,3-Dichloro Ketone Impurity;Sertraline Hydrochloride Impurity 3
• CAS NO: 152448-80-1
• Molecular Formula: C16H12Cl2O
• Molecular Weight: 291.17188
• Product Categories: Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 152448-80-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone(152448-80-1)
• EPA Substance Registry System: rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone(152448-80-1)

Safety Data

• Hazardous Substances Data: 152448-80-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
rac 4-(2,3-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is used as an impurity in the synthesis of Sertraline (S279975) for the development of antidepressant medications. Its presence as an isomer of the Sertraline intermediate 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone (D435705) is significant in the pharmaceutical industry, as it can impact the quality and efficacy of the final product.

Upstream product

• 90-15-3 α-naphthol 
• 95-50-1 1,2-dichloro-benzene 

Downstream Products

• 340830-05-9 2,3-dichlorosertraline-imine 

Relevant articles and documents

Method for preparing serrine hydrochloride intermediate and impurities

The invention relates to a method for preparing a sertraline hydrochloride intermediate and an impurity. The invention provides a method for refining 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone. The content of the impurity 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in the obtained product is less than 0.1%. The invention also relates to a method for preparing the isomer impurity 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone from the mother solution.

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)2O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)2O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline.

Asymmetric hydrogenation of N-Alkyl ketimines with phosphine-free, chiral, cationic Ru-MsDPEN catalysts

(Solvent) free and easy: A phosphine-free, chiral, cationic Ru-MsDPEN complex [(S,S)-1] is found to be an efficient catalyst for the enantioselective hydrogenation of a range of often-problematic N-alkyl ketimines (see scheme). This new method provides a more practical and greener synthetic approach to optically active amines, particularly N-alkyl amines, such as Sertraline.