83823-06-7

Basic information

• Product Name: 6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID
• Synonyms: IFLAB-BB F2121-0014;BUTTPARK 29\08-36;6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID;6-CHLORO-2H-CHROMENE-3-CARBOXYLIC ACID;TIMTEC-BB SBB005422;6-Chloro2Hü-1-benzopyran-3-carboxylic acid, 97%;6-Chloro-2H-chromene-3-carboxylic acid, 3-Carboxy-6-chloro-2H-1-benzopyran;2H-1-Benzopyran-3-carboxylicacid, 6-chloro-
• CAS NO: 83823-06-7
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.61
• Mol File: 83823-06-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 244-246°C
• Boiling Point: 367 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: /
• Density: 1.474 g/cm³
• Vapor Pressure: 4.96E-06mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 4426673
• CAS DataBase Reference: 6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID(83823-06-7)
• EPA Substance Registry System: 6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID(83823-06-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 22-24/25-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 83823-06-7(Hazardous Substances Data)

Usage

General Description

6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID, also known as 3-Carboxy-6-chlorocoumarin, is a chemical compound that belongs to the class of benzopyrans. It is a white crystalline powder with a molecular formula C10H5ClO4 and a molecular weight of 230.6 g/mol. 6-CHLORO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID is often used in the pharmaceutical industry for the synthesis of various drugs, particularly as an intermediate for the production of anticoagulant medications. It may also have potential applications in other fields such as agriculture and materials science. However, due to its chloro-substituted structure, it is important to handle this compound with caution and follow proper safety protocols when working with it.

InChI:InChI=1/C10H7ClO3/c11-8-1-2-9-6(4-8)3-7(5-14-9)10(12)13/h1-4H,5H2,(H,12,13)/p-1

Upstream product

• 83823-19-2 6-Chloro-2H-chromene-3-carboxylic acid amide 
• 57543-67-6 6-chloro-2H-chromene-3-carbonitrile 
• 1215266-96-8 tert-butyl 3-(5-chloro-2-hydroxyphenyl)-3-hydroxy-2-methylenepropanoate 
• 635-93-8 5-chlorosalicyclaldehyde 
• 57544-34-0 6-chloro-2H-chromene-3-carbaldehyde 

Downstream Products

• 306935-54-6 6-chloro-2H-1-benzopyran-3-carboxylic acid chloride 
• 1154742-96-7 6-chloro-2H-chromene-3-carboxylic acid [(R)-1-(2-fluoro-4-methanesulfonylamino-5-methylphenyl)ethyl]amide 
• 26371-48-2 6-chlorochroman-3-one 
• 257875-93-7 N-[3-[2-[bis(1-methylethyl)amino]ethoxy]-4-methoxyphenyl]-3-chloro-benzo[b]thiophene-2-carboxamide 
• 83823-23-8 (6-Chloro-2H-chromen-3-yl)-(4-imino-4H-pyridin-1-yl)-methanone 
• 83823-22-7 (6-Chloro-2H-chromen-3-yl)-(2-imino-2H-pyridin-1-yl)-methanone 
• 83823-20-5 6-Chloro-2H-chromene-3-carboxylic acid methylamide 
• 164265-01-4 (+/-)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid 

Relevant articles and documents

Discovery of (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide as potent and isoform selective ROCK2 inhibitors

ROCK1 and ROCK2 are highly homologous isoforms. Accumulated studies indicate that they have distinct different functions, and the development of isoform selective ROCK inhibitors will pave new roads for the treatment of various diseases. In this work, a series of amide-chroman derivatives were synthesized and biologically evaluated in order to develop potent and isoform selective ROCK2 inhibitors. Remarkably, (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide ((S)-7c) possessed ROCK2 inhibitory activity with an IC50 value of 3 nM and 22.7-fold isoform selectivity (vs. ROCK1). Molecular docking indicated that hydrophobic interactions were the key element for the high potency and isoform selectivity of (S)-7c. The binding free energies predicted by MM/GBSA were in good agreement with the experimental bioactivities, and the analysis of individual energy terms suggested that residue Lys105 in ROCK1 or Lys121 in ROCK2 was the key residue for the isoform selectivity of (S)-7c.

Strong base- or acid-mediated chemoselectivity shifts in the synthesis of 2H-chromene or coumarin derivatives from common Baylis-Hillman adducts

Abstract Reaction of tert-butyl 3-(2-hydroxyphenyl)-2-methylenepropanoate esters with aqueous KOH provides convenient and chemoselective one-pot access to 2H-chromene-3-carboxylic acids, the overall transformation involving tandem conjugate addition, hydrolysis and elimination steps. The methodology complements the chemoselective, acid-catalysed route to 3-substituted coumarins from the same substrates by switching the regioselectivity of cyclisation.

3-nitro-2H-chromenes as a new class of inhibitors against thioredoxin reductase and proliferation of cancer cells

A series of 3-nitrochromenes were designed and synthesized. These compounds showed good inhibitory activity against thioredoxin reductase (TrxR) and the proliferation of A549 cancer cells. The structure-activity relationship analysis indicates that the 3-nitrochromene scaffold is the crucial pharmacophore for achieving good inhibitory activity. The bromo-substitutions at the 6- and 8-position of 3-nitrochromene significantly increase the inhibitory activity. A series of 3-nitrochromenes were designed and synthesized. They showed good inhibitory activity against thioredoxin reductase and the proliferation of A549 cancer cells. Structure-activity relationship analysis revealed that the 3-nitrochromene scaffold is the crucial pharmacophore for achieving good inhibitory activity. Bromo-substitutions at the 6- and 8-position of 3-nitrochromene significantly increase the inhibitory activity. Copyright