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

Uses

Labelled Chlorferon is has α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Also used in the synthesis of fluorogenic substrates for the detection of bacterial β-Galactosidase.

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

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

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 
• 287397-86-8 coumaphos-d10 
• 64309-74-6 3-chloro-4-methyl-2-oxo-2H-chromen-7-ylacetate 
• 1352006-41-7 dibenzyl 3-chloro-4-methyl-2-oxo-2H-chromen-7-yl phosphate 

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.

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation

A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.