4-Hydroxycumarin

Bezeichnung:4-Hydroxycumarin

CAS-Nr1076-38-6

Englisch Name:4-Hydroxycoumarin

CBNumberCB0760607

SummenformelC9H6O3

Molgewicht162.14

MOL-Datei1076-38-6.mol

Synonyma

4-Hydroxycumarin

4-Hydroxycumarin physikalisch-chemischer Eigenschaften

Schmelzpunkt	211-213 °C (lit.)
Siedepunkt	228.82°C (rough estimate)
Dichte	1.1734 (rough estimate)
Dampfdruck	0.02Pa at 25℃
Brechungsindex	1.4500 (estimate)
storage temp.	Store below +30°C.
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Liquid
pka	4.50±1.00(Predicted)
Farbe	Clear colorless to slightly yellow
Wasserlöslichkeit	PRACTICALLY INSOLUBLE
BRN	129768
InChIKey	VXIXUWQIVKSKSA-UHFFFAOYSA-N
LogP	1.6-2.31 at 21.2℃
CAS Datenbank	1076-38-6(CAS DataBase Reference)
NIST chemische Informationen	4-Hydroxycoumarin(1076-38-6)
EPA chemische Informationen	2H-1-Benzopyran-2-one, 4-hydroxy- (1076-38-6)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	DJ3100000
Hazard Note	Irritant
TSCA	Yes
HS Code	29322980

Gefahreninformationscode (GHS)

4-Hydroxycoumarin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Yellow powder or chunks or Slightly yellow needle-like crystals. freely soluble in ethanol, ether and hot water. brown in color with ferric chloride.
Verwenden
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.
Verwenden
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.
Verwenden
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.
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
Synthese
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).
läuterung methode
Crystallise 4-hydroxycoumarin from water and dry it in a vacuum desiccator over pKEst Sicapent. [Beilstein 18/1 V 378.]

4-Hydroxycoumarin Upstream-Materialien And Downstream Produkte

4-Hydroxycumarin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1076-38-6, 4-Hydroxycoumarin Verwandte Suche:

Send Inquriy