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4-Hydroxycoumarin

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4-Hydroxycoumarin Basic information

Product Name:
4-Hydroxycoumarin
Synonyms:
  • 4-hydroxy-2h-1-benzopyran-2-on
  • COUMARINOL
  • HYDROXYCOUMARIN, 4-
  • 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-
  • 4-coumarinyl alcohol
  • 4-HYDROXY-CHROMEN-2-ONE
  • 4-HYDROXYCOUMARIN
  • 4-HYDROXYCUMARIN
CAS:
1076-38-6
MF:
C9H6O3
MW:
162.14
EINECS:
214-060-2
Product Categories:
  • Bioactive Small Molecules
  • Biochemicals and Reagents
  • Building Blocks
  • Cell Biology
  • Chemical Synthesis
  • H
  • FINE Chemical & INTERMEDIATES
  • Coumarins
  • Coumarin
  • Heterocyclic Building Blocks
  • Luminescent Compounds/Detection
  • Wavelength Index
  • Pharmaceutical intermediates
  • bc0001
  • 1076-38-6
Mol File:
1076-38-6.mol
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4-Hydroxycoumarin Chemical Properties

Melting point:
211-213 °C (lit.)
Boiling point:
228.82°C (rough estimate)
Density 
1.1734 (rough estimate)
vapor pressure 
0.02Pa at 25℃
refractive index 
1.4500 (estimate)
storage temp. 
Store below +30°C.
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
4.50±1.00(Predicted)
form 
Liquid
color 
Clear colorless to slightly yellow
Water Solubility 
PRACTICALLY INSOLUBLE
BRN 
129768
InChIKey
VXIXUWQIVKSKSA-UHFFFAOYSA-N
LogP
1.6-2.31 at 21.2℃
CAS DataBase Reference
1076-38-6(CAS DataBase Reference)
NIST Chemistry Reference
4-Hydroxycoumarin(1076-38-6)
EPA Substance Registry System
2H-1-Benzopyran-2-one, 4-hydroxy- (1076-38-6)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
DJ3100000
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29322980

MSDS

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4-Hydroxycoumarin Usage And Synthesis

Chemical Properties

Yellow powder or chunks or Slightly yellow needle-like crystals. freely soluble in ethanol, ether and hot water. brown in color with ferric chloride.

Uses

4-Hydroxycoumarin is a plant derived antioxidant, protecting against lipid peroxidation, as well as a potential inhibitor of HIV-1 Integrase. 4-Hydroxycoumarins are a very important class of biologically active drugs which are widely used as anticoagulants-Warfarin and Acenocoumarol.

Uses

4-Hydroxycoumarin is involved in annulation reactions, due to the relatively high acidity of the C-H bond at the 3-position: a three-component reaction with isocyanides and dialkyl acetylene dicarboxylates affords annulated 4H-pyrans.

Uses

4-Hydroxycoumarin may be regarded as a phenylenetetronic acid , and like tetronic acid forms condensation products with aldehydes.

Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium(III) chloride hydrate as a versatile homogeneous catalyst.

Definition

ChEBI: 4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 677, 1960 DOI: 10.1021/jo01074a630

Flammability and Explosibility

Not classified

Synthesis

4-Hydroxycoumarin is prepared by the reaction of o-hydroxyacetophenone and Diethyl carbonate. The steps are as follows:
General procedure: To a stirred mixture (1.15 mmol) and sodium hydride (138 mg, 5.75 mmol) in 5 ml dry toluene, a solution of the diethyl carbonate (1.15 mmol) in dry toluene was dropped. The mixture was reacted at 0°C for 30 min, then heated to reflux and reacted for another 4 h. The reaction mixture was quenched with water (20 mL) at ice bath and neutralized to pH 7 with 2 N HCl. The precipitate was filtered, washed with cold water and dried to get 6a-f. 1.2.1.1. 4-Hydroxy-2H-chromen-2-one (6a) White solidyield: 95; 1H NMR (600 MHz, DMSO-d6) δ 12.53 (s, 1H), 7.83 (d, J = 7.2 Hz, 1H), 7.65 (d, J = 7.8 Hz, 1H), 7.38-7.34 (m, 2H), 5.60 (s, 1H).

Purification Methods

Crystallise 4-hydroxycoumarin from water and dry it in a vacuum desiccator over pKEst Sicapent. [Beilstein 18/1 V 378.]

4-HydroxycoumarinSupplier

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