64169-66-0

Basic information

• Product Name: 5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE
• Synonyms: 5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE;5-BROMO-1-(4-FLUOROPHENYL)-PHTHOLIDE;5-BROMO-1-(4-FLUOROPHENY)PHTHALIDE;1-(4-Fluorophenyl)-5-broMophthalan
• CAS NO: 64169-66-0
• Molecular Formula: C₁₄H₁₀BrFO
• Molecular Weight: 293.13
• Mol File: 64169-66-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 359.8°C at 760 mmHg
• Flash Point: 203.5°C
• Appearance: /
• Density: 1.509g/cm³
• Vapor Pressure: 4.82E-05mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE(64169-66-0)
• EPA Substance Registry System: 5-BROMO-1-(4-FLUOROPHENYL)-PHTHALIDE(64169-66-0)

Safety Data

• Hazardous Substances Data: 64169-66-0(Hazardous Substances Data)

Usage

Uses

1-(4-Fluorophenyl)-5-bromophthalan is a metabolite of Citalopram (C505000), an inhibitor of serotonin (5-HT) uptake. Used as an antidepressant.

InChI:InChI=1/C14H10BrFO/c15-11-3-6-13-10(7-11)8-17-14(13)9-1-4-12(16)5-2-9/h1-7,14H,8H2

Upstream product

• 64169-34-2 5-bromophthalide 
• 64169-65-9 4-bromo-(2-hydroxymethyl)-phenyl-(4'-fluorophenyl)methanol 
• 7439-95-4 magnesium 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 64169-64-8 4-bromo-4'-fluoro-2-(hydroxymethyl)benzophenone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 41377-44-0 4-Fluorbenzoesaeure-5-bromsalicyliden-hydrazon 

Downstream Products

• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 62498-69-5 didesmethylcitalopram 
• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 

Relevant articles and documents

Efficient synthesis of functionalized 1,3-dihydroisobenzofurans from salicylaldehydes: Application to the synthesis of escitalopram

An efficient synthesis of substituted 1,3-dihydroisobenzofurans is developed. In this novel route, o-aroylbenzaldehydes, as key intermediates, can be obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. The mild and general st

PROCESS FOR PREPARING 5-SUBSTITUTED -1-(4-FLUOROPHENYL) -1,3-DIHYDROISOBENZOFURANS

The present invention relates to a method for preparation and isolation of hitherto unknown solid boron complex of formula (v), which are obtained when 5-substituted phthalides are reacted with a solution of 4-fluorophenylmagnesiumbromide, followed by in situ reduction and complex formation in the presence of sodiumborohydride. Such boron complexes can be conveniently filtered to remove structurally similar impurities and subsequently subjected to cyclisation reaction in acidic medium to get high pure 5-substituted phthalens, which are key starting materials for manufacturing citalopram and pharmaceutically acceptable acid addition salts.

PROCESS FOR THE PREPARATION OF HIGH PURITY CITALOPRAM AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

This invention discloses an improved process for the preparation of high purity citalopram base and its hydrobromide salt of formulae (I) and (Ia): which comprises: i. Isolation of crude citalopram base after water work up of the reaction into a non polar aromatic or dialkyl ether solvent. ii. Extraction of the citalopram base into aqueous organic acid. iii. Neutralization of acid layer with organic base to a controlled pH (7.0-8.0) iv. Extraction of the pure base into a non-polar aromatic or dialkyl ether solvent and crytallization form the same solvent after concentrating to certain volume under reduced pressure. v. Preparation of high purity citalopram hydrobromide in a non-polar aromatic or dialkyl ether solvent using 40-50 % HBr in acetic acid as HBr source and crystallizing out form the same solvent. Alternatively preparation of HBr salt in aqueous medium using aqueous HBr and crystallizing out from the same medium at 0 10 °C. vi. Recrystallization of high purity citalopram hydrobromide salt of pharmaceutically acceptable grade form a mixture of alcoholic solvent.