4-Hydroxycoumarin Property

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)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

4-Hydroxycoumarin Chemical Properties,Usage,Production

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.]