19484-57-2

Basic information

• Product Name: 6-CHLORO-4-HYDROXYCOUMARIN
• Synonyms: 6-CHLORO-4-HYDROXY-2H-CHROMEN-2-ONE;6-CHLORO-4-HYDROXYCOUMARIN;AURORA KA-6040;6-CHLORO-4-HYDROXYCOUMARIN 97%;4-Hydroxy-6-chloro-2H-1-benzopyran-2-one;4-Hydroxy-6-chlorocoumarin;6-Chloro-4-hydroxy-2H-1-benzopyran-2-one;6-Chloro-4-hydroxycoumarin,97%
• CAS NO: 19484-57-2
• Molecular Formula: C₉H₅ClO₃
• Molecular Weight: 196.59
• EINECS: 145-863-9
• Product Categories: Coumarins;Building Blocks;CoumarinsHeterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 19484-57-2.mol
• Article Data: 26

Chemical Properties

• Melting Point: 291 °C (dec.)(lit.)
• Boiling Point: 392.613 °C at 760 mmHg
• Flash Point: 191.246 °C
• Appearance: Slightly beige/Crystalline Powder
• Density: 1.585 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 6-CHLORO-4-HYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-4-HYDROXYCOUMARIN(19484-57-2)
• EPA Substance Registry System: 6-CHLORO-4-HYDROXYCOUMARIN(19484-57-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 19484-57-2(Hazardous Substances Data)

Usage

Chemical Properties

Slightly beige crystalline powder

Uses

6-Chloro-4-hydroxycoumarin may be employed for the synthesis of 5-alkylidene-4-chloro-5H-1,2,3-dithiazoles. It may be employed for the synthesis of 6-[(coumarinyl-1-aryl-propionyl]benzoxazinones.

General Description

6-Chloro-4-hydroxycoumarin is a substituted 4-hydroxycoumarin. It participates in the Fe/Acetic acid (AcOH) catalyzed synthesis of various biologically active compounds.

InChI:InChI=1/C9H5ClO3/c10-5-1-2-8-6(3-5)7(11)4-9(12)13-8/h1-4,11H

Upstream product

• 69693-00-1 6-chloro-2-methyl-4H-chromen-4-one 
• 876-27-7 4-chlorophenyl acetate 
• 106-48-9 4-chloro-phenol 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 118-93-4 o-hydroxyacetophenone 
• 67829-05-4 1-(3-chlorophenyl)-2-hydroxyethanone 
• 105-58-8 Diethyl carbonate 
• 141-82-2 malonic acid 
• 288087-81-0 (Z)-3-Amino-4,4,4-trichloro-1-(5-chloro-2-hydroxy-phenyl)-but-2-en-1-one 
• 7446-70-0 aluminium trichloride 
• 15014-20-7 bis(4-chlorophenyl) malonate 
• 133406-29-8 6-chloro-2-(trichloromethyl)-4H-chromen-4-one 
• 33533-99-2 6-chloro-4H-chromen-4-one 

Downstream Products

• 103167-19-7 3,3'-((3-methoxy,4-hydroxyphenyl)methylene)bis(6-chloro-4-hydroxy-2H-chromen-2-one) 
• 131691-17-3 6-chlorocoumarin-4-yl α-isopropyl-4-chlorophenylacetate 
• 1187472-33-8 6-chloro-4-(phenylethynyl)-2H-chromen-2-one 
• 1187472-34-9 6-chloro-4-((4-methoxyphenyl)ethynyl)-2H-chromen-2-one 
• 1198104-39-0 (E)-6-chloro-3-(1,3-diphenylallyl)-4-hydroxy-2H-chromen-2-one 
• 1408463-40-0 2-amino-9-chloro-4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 
• 1408463-43-3 2-amino-9-chloro-4-(5-chloro-1-(3-chlorophenyl)-3-methyl-1H-pyrazol-4-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 

Relevant articles and documents

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Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives

A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.