372941-48-5

Basic information

• Product Name: 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarbonitrile
• Synonyms: 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarbonitrile;Des[3-(Dimethylamino)propyl] 3-Oxocitalopram
• CAS NO: 372941-48-5
• Molecular Formula: C₁₅H₈FNO₂
• Molecular Weight: 253.23
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Intermediates;Aromatics, Heterocycles, Intermediates
• Mol File: 372941-48-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 173-175?C
• Boiling Point: 433.919°C at 760 mmHg
• Flash Point: 216.227°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Refrigerator
• Solubility: DMF, DMSO, Methanol
• CAS DataBase Reference: 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarbonitrile(372941-48-5)
• EPA Substance Registry System: 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarbonitrile(372941-48-5)

Safety Data

• Hazardous Substances Data: 372941-48-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 372941-48-5 differently. You can refer to the following data:
1. An intermediate for the preparation of Citalopram
2. An intermediate for the preparation of Citalopram.

InChI:InChI=1/C15H8FNO2/c16-11-4-2-10(3-5-11)14-12-6-1-9(8-17)7-13(12)15(18)19-14/h1-7,14H

Synthetic route

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (64169-67-1) → 1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile (372941-48-5)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; oxygen; diphenyldisulfane In 1,4-dioxane at 80℃; under 760.051 Torr; for 15h; Schlenk technique; regioselective reaction;	50%

1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid amide (372941-46-3) → 1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile (372941-48-5)

Conditions	Yield
In thionyl chloride; N,N-dimethyl-formamide	7.8 g (62%)

Upstream product

• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 372941-46-3 1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid amide 

Relevant articles and documents

Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp3 C-H bonds with molecular oxygen

A ligand-free iron-catalyzed method for the oxygenation of benzylic sp3 C-H bonds by molecular oxygen (1 atm) using a thiyl radical as a cocatalyst has been developed. This transformation provides a facile access to amides, esters and ketones from readily accessible corresponding amines, ethers and alkanes. It features high regioselectivity, mild oxidative conditions and excellent functional group compatibility, providing good opportunities to the site-selective functionalization of complex molecules. Preliminary mechanistic studies suggest that this reaction may not undergo a benzylic cation intermediate pathway and the carbonyl oxygen atom in the products may be derived from molecular oxygen.