409346-73-2

Basic information

• Product Name: rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde
• Synonyms: rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde;rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde DISCONTINUED. NOT STABLE
• CAS NO: 409346-73-2
• Molecular Formula: C₁₀H₉FO₂
• Molecular Weight: 180.1756632
• Product Categories: Aromatics;Heterocycles;Intermediates;Miscellaneous Reagents;Aromatics, Heterocycles, Intermediates, Miscellaneous Reagents
• Mol File: 409346-73-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde(409346-73-2)
• EPA Substance Registry System: rac 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde(409346-73-2)

Safety Data

• Hazardous Substances Data: 409346-73-2(Hazardous Substances Data)

Usage

Uses

Intermediate in the production of Nebivolol

Upstream product

• 105300-38-7 6-fluoro-4H-chromen-4-one 
• 105300-39-8 6-fluoro-4-oxochromane-2-carbonitrile 
• 874649-82-8 (-)-(R)-methyl 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylate 
• 99199-60-7 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid 
• 878208-57-2 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid piperidine amide 
• 99199-59-4 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid 
• 79-37-8 oxalyl dichloride 
• 67-68-5 dimethyl sulfoxide 
• 121-44-8 triethylamine 
• 99199-62-9 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol 

Downstream Products

• 99199-90-3 6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran 
• 793669-26-8 [R*(R*)]-6-fluoro-3,4-dihydro-2-oxiran-2-yl-2H-benzopyran 
• 793669-26-8 [R*(S*)]-6-fluoro-3,4-dihydro-2-oxiran-2-yl-2H-benzopyran 
• 129050-27-7 (S*,R*)-(+/-)-α-[(benzylamino)methyl]-(6-fluoro-2-chromanyl)methanol 
• 152520-56-4 nebivolol hydrochloride 
• 99200-09-6 nebivolol 
• 129050-27-7 (R*,R*)-(±)-α-[(benzylamino)methyl](6-fluoro-2-chromanyl)methanol 
• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 793669-26-8 [1S*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 920299-33-8 (R)-1-((R)-6-Fluoro-chroman-2-yl)-2-[(S)-2-((R)-6-fluoro-chroman-2-yl)-2-hydroxy-ethylamino]-ethanol; hydrochloride 
• 152520-56-4 nebivolol hydrochloride 
• 118457-14-0 R 67142 
• 118457-16-2 nebivolol 
• 9920-09-6 α,α'-iminobis(methylene)bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride 

Relevant articles and documents

B(C6F5)3-catalyzed divergent cyanosilylations of chromones dependent on temperature

A B(C6F5)3-catalyzed divergent cyanosilylation of chromones has been successfully realized. A variety of 4-oxochromane-2-carbonitriles were furnished as kinetic products in high yields via 1,4-cyanosilylations. An unexpected C-O bond cyanosilylation was achieved when the temperature was raised to 80 °C, affording 4-oxo-4-(2-hydroxylphenyl)but-2-enenitriles as thermodynamic products in 72-94% yields, which was confirmed by DFT results.

Preparation method of 6-fluorochromane-2-formaldehyde as nebivolol intermediate

The invention discloses a preparation method of 6-fluorochromane-2-formaldehyde used as a key intermediate of nebivolol for treating essential hypertension. At the temperature of 50 to 80 DEG C, 6-fluorochromane-2-methanol is dissolved in a solvent, in oxygen atmosphere, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), cuprous bromide, 2,2-bipyridine and N-methylimidazole (NMI) are catalytically reacted to obtain 6-fluorochromane-2-formaldehyde. The synthetic method of 6-fluorochromane-2-formaldehyde used as the nebivolol intermediate provided by the invention is mild in reaction condition and simple to operate; the product purity LC of 6-fluorochromane-2-formaldehyde can reach 95%, the yield of 6-fluorochromane-2-formaldehyde is 82% or more, and the used catalysts are environment-friendly and suitable for industrial production.

A PROCESS FOR THE PREPARATION OF 6-FLUORO-3,4-DIHYDRO-2H-CHROMENE- 2-CARBALDEHYDE

The present invention relates to a process for ihe preparation of 6-f!uoro-3,4-dihydro- 2H-chromene-2-carbaidehyde which is useful as an Intermediate in the synthesis of Nebivolol or its pharmaceutical acceptable salts.