3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Chemical Properties

Melting point:

240-244 °C (lit.)

Boiling point:

405.8±45.0 °C(Predicted)

Density 

1.48±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

7.43±0.20(Predicted)

form 

Powder

color 

White to off-white

λmax

332nm(EtOH)(lit.)

CAS DataBase Reference

6174-86-3(CAS DataBase Reference)

EPA Substance Registry System

2H-1-Benzopyran-2-one, 3-chloro-7-hydroxy-4-methyl- (6174-86-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

TSCA 

Yes

HS Code 

29329900

MSDS

• Language:English Provider:SigmaAldrich

3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Usage And Synthesis

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.

Definition

ChEBI: Chlorferron is an organochlorine compound. It is functionally related to a 4-methylumbelliferone.

Synthesis

GENERAL STEPS: Resorcinol (2.0 g, 18.2 mmol) was dissolved in dioxane and the solution was cooled to 0 °C. Concentrated sulfuric acid (0.5 mL) was added slowly and dropwise at 25 °C. Subsequently, ethyl 2-chloroacetoacetate (2.8 g, 21.8 mmol) was added and the reaction mixture was heated to 60 °C and maintained at this temperature for 4 hours. After completion of the reaction, the mixture was poured into cold water, the precipitate was collected by filtration and dried under reduced pressure. Finally, the product was purified by recrystallization from methanol to give 3-chloro-7-hydroxy-4-methylcoumarin (6a) as white needle-like crystals.

References

[1] Chemistry - A European Journal, 2012, vol. 18, # 32, p. 9901 - 9910
[2] Synthesis, 2006, # 11, p. 1895 - 1897
[3] Monatshefte fur Chemie, 2008, vol. 139, # 7, p. 805 - 808
[4] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 153 - 165
[5] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3279 - 3281

3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN(6174-86-3)Related Product Information

• Dimethyl sulfate
• Rhamnosylvitexin
• COUMAPHOS-OXON
• 4-Methylcumarin
• Coumarin
• 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN
• Phosphorothioic acid, O,O-diethyl ester, O-ester with 3-chloro-7-hydroxy-4-methylcoumarin
• 7-(CARBOXYMETHOXY)-3-CHLORO-4-METHYLCOUMARIN
• 6-CHLORO-4-HYDROXY-7-METHYLCOUMARIN
• 6-CHLORO-7-HYDROXY-4-METHYLCOUMARIN
• haloxon
• DIMETHYL-PHOSPHORAMIDIC ACID 3-CHLORO-4-METHYL-2-OXO-2H-CHROMEN-7-YL ESTER ETHYL ESTER
• 3-CHLORO-7-DIMETHOXYTHIOPHOSPHORYLOXY-4-METHYL COURMAIN
• CYCLOHEXYL-METHYL-PHOSPHINIC ACID 3-CHLORO-4-METHYL-2-OXO-2H-CHROMEN-7-YL ESTER
• 3-CHLORO-7,8-DIHYDROXY-4-METHYL-2H-CHROMEN-2-ONE
• PHOSPHORIC ACID 3-CHLORO-4-METHYL-2-OXO-2H-CHROMEN-7-YL ESTER DIMETHYL ESTER
• 3-CHLORO-6,7-DIHYDROXY-4-METHYL-2H-CHROMEN-2-ONE
• METHYL-PHOSPHONIC ACID 3-CHLORO-4-METHYL-2-OXO-2H-CHROMEN-7-YL ESTER ETHYL ESTER