4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE Chemical Properties

Melting point:

180-183°C

Boiling point:

409.6±45.0 °C(Predicted)

Density 

1.442±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Solid

pka

7.72±0.20(Predicted)

color 

Off-white to pink

Appearance

Solid Powder

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2932209090

4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE Usage And Synthesis

Description

4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one is a thiol-reactive, cell-permeant fluorescent probe that easily passes through cell membranes.

Uses

Fluorescent Thiol-Reactive cell permeant probe

Synthesis

A mixture of resorcinol (1.0 mmol), ethyl 4-chloroacetoacetate (1.5 mmol) and MNESA (0.075 g) was placed in a round-bottomed flask and the reaction was stirred at 90 °C. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was cooled to room temperature. The catalyst MNESA was separated from the reaction mixture using an external magnetic field. Subsequently, water was added to the reaction mixture and the target product, 4-chloromethyl-7-hydroxychromen-2-one, was extracted with ethyl acetate (EtOAc, 3 × 10 mL). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. For further purification, the crude product was recrystallized in ethanol to obtain high purity 4-chloromethyl-7-hydroxychromen-2-one.

References

[1] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6119 - 6121
[2] Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 287 - 290
[3] Synthetic Communications, 2008, vol. 38, # 13, p. 2082 - 2088
[4] Journal of Chemical Research, 2008, # 4, p. 232 - 234
[5] Synthetic Communications, 2010, vol. 40, # 22, p. 3358 - 3364

Excitation / Emission Maximum

348 nm/423 nm

4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE(25392-41-0)Related Product Information

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