7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN Chemical Properties

Melting point:

178-180 °C (lit.)

Boiling point:

311.4±42.0 °C(Predicted)

Density 

1.4435 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMF: soluble

form 

powder to crystal

pka

7.23±0.20(Predicted)

color 

White to Light yellow to Light orange

λmax

330nm(Toluene)(lit.)

BRN 

210932

InChI

InChI=1S/C10H5F3O3/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4,14H

InChIKey

CCKWMCUOHJAVOL-UHFFFAOYSA-N

SMILES

C1(=O)OC2=CC(O)=CC=C2C(C(F)(F)F)=C1

CAS DataBase Reference

575-03-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-25

Safety Statements 

26-36-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

F 

8-10

HazardClass 

IRRITANT

HS Code 

29322090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN Usage And Synthesis

Description

7-Hydroxy-4-(trifluoromethyl)coumarin can be used as a reference standard for fluorescent pH indicator.

Chemical Properties

Off-white to light yellow or pink powder

Uses

Suitable as pH-indicator. Trifluoromethylumbelliferone is a slightly longer wavelength analog of 4-methylcoumarin (4-MU) with a pKa that more closely matches physiological pH values.

Uses

7-Hydroxy-4-(trifluoromethyl)coumarin is an halogenated metabolite of Coumarin (C755380), an naturally occurring organic compound that exists in many plants. Coumarin is the precursor molecule in the synthesis of various synthetic anti-coagulant such as warfarin (W498500)/.

General Description

7-Hydroxy-4-(trifluoromethyl)coumarin is a class of 7-hydroxycoumarin that is majorly used as laser dyes. It has a characterized emission spectra and may be used in excited state proton transfer (ESPT).

Synthesis

GENERAL METHOD: Iodine (25 mol%) was added to a mixture of resorcinol (5 mmol) and ethyl 4,4,4-trifluoroacetoacetate (6 mmol) in toluene (1 mL). The reaction mixture was heated and stirred at 90 °C for 18 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and washed with distilled water (10 mL). The combined organic layers were dried with anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. The product was purified by fast column chromatography (silica gel, eluent: hexane/ethyl acetate = 95/5 to 80/20).

References

[1] Synthetic Communications, 2006, vol. 36, # 20, p. 2949 - 2956
[2] Monatshefte fur Chemie, 2013, vol. 144, # 3, p. 411 - 414
[3] Tetrahedron Letters, 2002, vol. 43, # 50, p. 9195 - 9197
[4] Synthetic Communications, 2004, vol. 34, # 21, p. 3997 - 4003
[5] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6715 - 6717

7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN(575-03-1)Related Product Information

• Dimethyl sulfate
• 6,7-DIMETHOXY-4-(TRIFLUOROMETHYL)COUMARIN
• 4-(TRIFLUOROMETHYL)UMBELLIFERYL-BETA-D-GALACTOPYRANOSIDE
• 6,7-Diethoxy-4-(trifluoromethyl)coumarin
• 4-(TRIFLUOROMETHYL)UMBELLIFERYL BUTYRATE
• 4-TRIFLUOROMETHYLUMBELLIFERYL-A-D-N-ACETYLNEURAMINIC ACID
• 4-(TRIFLUOROMETHYL)UMBELLIFERYL-BETA-D-GLUCOPYRANOSIDE
• 7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN
• 7-BENZYLOXY-4-(TRIFLUOROMETHYL)COUMARIN
• 4-(TRIFLUOROMETHYL)UMBELLIFERYL OLEATE
• 4-(TRIFLUOROMETHYL)UMBELLIFERYL ACETATE
• 6,7-DIHYDROXY-4-(TRIFLUOROMETHYL)COUMARIN
• 7-ETHOXY-4-(TRIFLUOROMETHYL)COUMARIN
• 6-CHLORO-7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN,6-chloro-7-hydroxy-4-(trifluoromethyl)coumarin 97%,6-chloro-7-hydroxy-4-(trifluoromethyl)coumarin97%
• 4-TRIFLUOROMETHYL-7-HYDROXYCOUMARIN GLUCURONIDE POTASSIUM SALT
• 7-METHOXY-4-(TRIFLUOROMETHYL)COUMARIN