6174-86-3

Basic information

• Product Name: 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN
• Synonyms: AKOS BBS-00008033;3-CHLORO-4-METHYLUMBELLIFERONE;3-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE;3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN;3-chloro-7-hydroxy-4-methyl-2h-1-benzopyran-2-on;3-chloro-7-hydroxy-4-methyl-2-benzopyrone;3-CHLORO-7-HYDROXY-4-METHYL-2H-1-BENZOPYRAN-2-ONE;3-Chloro-4-methyl-7-hydroxycoumarine
• CAS NO: 6174-86-3
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.61
• EINECS: 228-217-8
• Product Categories: Coumarins
• Mol File: 6174-86-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: 240-244 °C(lit.)
• Boiling Point: 405.8°C at 760 mmHg
• Flash Point: 199.2°C
• Appearance: White to off-white/Powder
• Density: 1.48g/cm³
• Vapor Pressure: 3.63E-07mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.43±0.20(Predicted)
• CAS DataBase Reference: 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN(6174-86-3)
• EPA Substance Registry System: 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN(6174-86-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 6174-86-3(Hazardous Substances Data)

Usage

Description

3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN is a chemical compound belonging to the class of coumarins, which are naturally occurring organic compounds found in plants. This specific compound is characterized by the presence of a chlorine atom at the 3rd position, a hydroxyl group at the 7th position, and a methyl group at the 4th position in its molecular structure. It exhibits various biological activities and has potential applications in different fields due to its unique properties.

Uses

Used in Pharmaceutical Industry:
3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN is used as an α-Glucosidase inhibitor for its antihyperglycemic activity. This application is particularly relevant in the development of treatments for diabetes, as it helps to regulate blood sugar levels by inhibiting the enzyme α-Glucosidase, which is responsible for breaking down complex carbohydrates into glucose.
Used in Research and Diagnostics:
3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN is also used in the synthesis of fluorogenic substrates for the detection of bacterial β-Galactosidase. This application is crucial in research and diagnostic laboratories, as it aids in the identification and study of bacterial strains that produce this enzyme, which is involved in various biological processes and can be an indicator of certain infections or conditions.

InChI:InChI=1/C10H7ClO3/c1-5-7-3-2-6(12)4-8(7)14-10(13)9(5)11/h2-4,12H,1H3

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 64309-74-6 3-chloro-4-methyl-2-oxo-2H-chromen-7-ylacetate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 108-46-3 recorcinol 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 56-72-4 coumaphos 
• 2747-05-9 4-methylumbelliferyl acetate 
• 4755-81-1 methyl 2-chloroacetoacetate 

Downstream Products

• 5826-75-5 3-chloro-7-dimethoxythiophosphoryloxy-4-methyl-coumarin 
• 56-72-4 coumaphos 
• 354130-56-6 3-chloro-4-methyl-7-propionyloxy-coumarin 
• 28045-90-1 3-Chloro-7-methoxy-4-methylcoumarin 
• 115929-21-0 7-allyloxy-4-methyl-3-chlorocoumarin 
• 287397-86-8 coumaphos-d10 
• 321-54-0 Coralox 
• 176446-74-5 2-[(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid 
• 64309-74-6 3-chloro-4-methyl-2-oxo-2H-chromen-7-ylacetate 
• 1253783-64-0 3-({5-[(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]pentyl}oxy)-5-hydroxy-N,N,N-trimethylbenzenaminium iodide 
• 1253783-68-4 3-[(3-{[(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]methyl}benzyl)oxy]-5-hydroxy-N,N,N-trimethylbenzenaminium iodide 
• 1253783-46-8 3-chloro-7-({5-[3-(dimethylamino)-5-hydroxyphenoxy]pentyl}oxy)-4-methyl-2H-chromen-2-one 
• 1253783-49-1 3-chloro-7-[(3-{[3-(dimethylamino)-5-hydroxyphenoxy]methyl}benzyl)oxy]-4-methyl-2H-chromen-2-one 
• 1253783-83-3 7-{[3-(bromomethyl)benzyl]oxy}-3-chloro-4-methyl-2H-chromen-2-one 

Relevant articles and documents

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A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X +) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G0/G1 phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis.