64169-39-7

Basic information

• Product Name: 5-BroModescyano CitalopraM
• Synonyms: 5-BroModescyano CitalopraM;1-(4-Fluorophenyl)-1-(3-diMethylaMinopropyl)-5-broMophthalane;5-BroMo-1-(4-fluorophenyl)-1,3-dihydro-N,N-diMethyl-1-isobenzofuranpropanaMine;Citalopram EP Impurity F
• CAS NO: 64169-39-7
• Molecular Formula: C₁₉H₂₁BrFNO
• Molecular Weight: 378.2785432
• Product Categories: Amines;Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 64169-39-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 417.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.318±0.06 g/cm3(Predicted)
• PKA: 9.58±0.28(Predicted)
• CAS DataBase Reference: 5-BroModescyano CitalopraM(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BroModescyano CitalopraM(64169-39-7)
• EPA Substance Registry System: 5-BroModescyano CitalopraM(64169-39-7)

Safety Data

• Hazardous Substances Data: 64169-39-7(Hazardous Substances Data)

Usage

Uses

5-Bromodescyano Citalopram (Citalopram EP Impurity F) is a Citalopram (C505000) impurity.

Upstream product

• 488148-10-3 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzobromide 
• 508169-73-1 (4-bromo-2-hydroxyethyl) phenyl-(4-fluorophenyl)-(3-dimethylaminopropyl) methanol hydrochloride 
• 50-00-0 formaldehyd 

Downstream Products

• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 62498-67-3 rac-desmethylcitalopram 
• 1241889-90-6 (E)-3-(1-(4-fluorophenyl)-5-styryl-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-92-8 3-(1-(4-fluorophenyl)-5-(3-methoxyphenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-89-3 3-(5-(3-amino-phenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-98-4 3-(5-(3-chlorophenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-97-3 3-(5-(3-fluorophenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 64372-43-6 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine oxalate 
• 1241889-91-7 3-(5-(3-cyanophenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-94-0 3-(5-(3,5-difluorophenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-93-9 3-(5-(3,4-dichlorophenyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-99-5 (E)-3-(5-(4-chlorostyryl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1241889-88-2 3-(1-(4-fluorophenyl)-5-phenyl-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1303605-20-0 [⁽¹²⁵⁾I]-{3-[5-iodo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl]propyl}dimethylamine 

Relevant articles and documents

Copper-catalysed cyanoalkylative cycloetherification of alkenes to 1,3-dihydroisobenzofurans: development and application to the synthesis of citalopram

A copper-catalysed cyanoalkylative cycloetherification of alkenes was developed. Heating a solution of substituted (2-vinylphenyl)methanol in MeCN/MeOH (v/v 7/3) in the presence of a catalytic amount of copper(ii) tetrafluoroborate hydrate [Cu(BF4)2·6H2O], bathophenanthroline, K3PO4, BnOH and (tBuO)2 afforded 1,3-dihydroisobenzofurans (phthalanes) via formation of one C(sp3)-C(sp3) and one C(sp3)-O bonds. A concise synthesis of citalopram, a marketed anti-depressant drug, was accomplished by applying this novel synthetic transformation.

Structure-activity relationships for a novel series of citalopram (1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5- carbonitrile) analogues at monoamine transporters

(±)-Citalopram (1, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1, 3-dihydroisobenzofuran-5-carbonitrile), and its eutomer, escitalopram (S-(+)-1) are selective serotonin reuptake inhibitors (SSRIs) that are used clinically to treat anxiety and depression. To further explore structure-activity relationships at the serotonin transporter (SERT), a series of (±)-4- and 5-substituted citalopram analogues were designed, synthesized, and evaluated for binding at the SERT, dopamine transporter (DAT) and norepinephrine transporter (NET) in native rodent tissue. Many of these analogues showed high SERT binding affinities (Ki = 1-40 nM) and selectivities over both NET and DAT. Selected enantiomeric pairs of analogues were synthesized and both retained enantioselectivity as with S- and R-1, wherein S > R at the SERT. In addition, the enantiomeric pairs of 1 and 5 were tested for binding at the homologous bacterial leucine transporter (LeuT), wherein low affinities and the absence of enantioselectivity suggested distinctive binding sites for these compounds at SERT as compared to LeuT. These novel ligands will provide molecular tools to elucidate drug-protein interactions at the SERT and to relate those to behavioral actions in vivo.

Method of manufacturing citalopram

The present invention provides, inter alia, a novel process for the preparation of Citalopram, a known antidepressant.