4-Hydroxycoumarin

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
4-Hydroxycoumarin Structure
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)
pka4.50±1.00(Predicted)
form Liquid
color Clear colorless to slightly yellow
Water Solubility PRACTICALLY INSOLUBLE
BRN 129768
InChIKeyVXIXUWQIVKSKSA-UHFFFAOYSA-N
LogP1.6-2.31 at 21.2℃
CAS DataBase Reference1076-38-6(CAS DataBase Reference)
NIST Chemistry Reference4-Hydroxycoumarin(1076-38-6)
EPA Substance Registry System2H-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 Information
ProviderLanguage
4-Hydroxy-1-benzopyran-2-one English
SigmaAldrich English
ACROS English
ALFA English
4-Hydroxycoumarin Usage And Synthesis
Chemical PropertiesYellow powder or chunks or Slightly yellow needle-like crystals. freely soluble in ethanol, ether and hot water. brown in color with ferric chloride.
Uses4-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.
Uses4-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.
Uses4-Hydroxycoumarin may be regarded as a phenylenetetronic acid , and like tetronic acid forms condensation products with aldehydes.
RuCl3.nH2O catalyzed synthesis of biscoumarins
Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium(III) chloride hydrate as a versatile homogeneous catalyst.

DefinitionChEBI: 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 ExplosibilityNotclassified
Purification MethodsCrystallise 4-hydroxycoumarin from water and dry it in a vacuum desiccator over pKEst Sicapent. [Beilstein 18/1 V 378.]
Methylparaben 4-Hydroxybenzoic acid Esculetin 7-HYDROXYCOUMARIN, 1GM, NEAT,7-Hydroxycoumarin,98%,ACETYL-7-HYDROXYCOUMARIN, 8-(RG) Coumarin Coumarine311 Dihydrocoumarin 2-Hydroxyphenylacetic acid 3-Hydroxybenzoic acid 6-Hydroxycoumarin 4-HYDROXY MEPHENYTOIN CoumarinDerivatives 4-Hydroxybenzaldehyde 4'-Hydroxyacetophenone Ethyl acetate 4-Methoxyphenol 4-Hydroxy-D-(-)-2-phenylglycine CHLOROPHOSPHONAZO III

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