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

Odor

Very faint woody-medicinal odor with a with Aluminum chloride. nut-like, hcrbaccous tone

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)

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

• Language:English Provider:4-Hydroxy-1-benzopyran-2-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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-Hydroxycoumarin(1076-38-6)Related Product Information

• 4-Methoxyphenol
• Methylparaben
• 3-Hydroxybenzoic acid
• CHLOROPHOSPHONAZO III
• 4-Hydroxy-D-(-)-2-phenylglycine
• Ethyl acetate
• 4-Hydroxybenzaldehyde
• 4-Hydroxybenzoic acid
• Dihydrocoumarin
• 2-Hydroxyphenylacetic acid
• 4'-Hydroxyacetophenone
• Coumarin
• Centchroman
• Triclosan
• 4-Methylumbelliferone
• Warfarin
• 4,4'-(Disulfanediyl)bis(2,6-di-tert-butylphenol)
• r-(+)-3-acetonybenzyl)-4-hydroxycoumarin,(S)-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin