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7,8-Dihydroxycoumarin

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Name

7,8-Dihydroxycoumarin

EINECS 207-632-8
CAS No. 486-35-1 Density 1.563 g/cm3
PSA 70.67000 LogP 1.20420
Solubility N/A Melting Point 265-268 °C (dec.)
Formula C9H6O4 Boiling Point 430.4 °C at 760 mmHg
Molecular Weight 178.144 Flash Point 184.5 °C
Transport Information N/A Appearance solid
Safety 22-24/25-36-26 Risk Codes 25-36/37/38
Molecular Structure Molecular Structure of 486-35-1 (7,8-Dihydroxycoumarin) Hazard Symbols IrritantXi
Synonyms

Daphnetin;2H-1-Benzopyran-2-one, 7,8-dihydroxy- (9CI);7,8-dihydroxy-coumarin;Daphnetol;5-18-03-00211 (Beilstein Handbook Reference);7,8-Dihydroxy-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one,7,8-dihydroxy-;7,8-dihydroxychromen-2-one;

Article Data 40

7,8-Dihydroxycoumarin Synthetic route

471-25-0

Propiolic acid

87-66-1

2-hydroxyresorcinol

486-35-1

daphnetin

Conditions
ConditionsYield
With ytterbium(III) trifluoromethanesulfonate hydrate at 80℃; for 0.0333333h; Reagent/catalyst; Microwave irradiation;98%
With sulfuric acid at 120℃; for 1h;70%
With sulfuric acid at 120℃; for 0.5h;59%
With sulfuric acid at 124 - 126℃; for 0.833333h;53.4%
With sulfuric acid at 125℃; for 0.833333h;
104819-86-5

7,8-dibenzyloxycoumarin

486-35-1

daphnetin

Conditions
ConditionsYield
With aluminum tri-bromide In nitrobenzene for 0.0833333h;80%
617-48-1

malic acid

87-66-1

2-hydroxyresorcinol

486-35-1

daphnetin

Conditions
ConditionsYield
With sulfuric acid65%
With sulfuric acid at 120 - 130℃; for 1h;61%
Stage #1: malic acid With sulfuric acid at 20℃; for 0.166667h;
Stage #2: 2-hydroxyresorcinol at 20 - 120℃; for 2h;
40%
2144-08-3

2,3,4-trihydroxybenzylaldehyde

1099-45-2

ethyl (triphenylphosphoranylidene)acetate

486-35-1

daphnetin

Conditions
ConditionsYield
for 0.25h; Inert atmosphere; Reflux;65%
for 4h; Reflux; Inert atmosphere;65%
93-35-6

7-hydroxy-2H-chromen-2-one

486-35-1

daphnetin

Conditions
ConditionsYield
With 2-iodoxybenzoic acid In dimethyl sulfoxide at 25℃; for 2h; Time; regioselective reaction;59%
110-16-7

maleic acid

87-66-1

2-hydroxyresorcinol

486-35-1

daphnetin

Conditions
ConditionsYield
With sulfuric acid20%
2067-86-9

8-formyl-7-hydroxycoumarin

486-35-1

daphnetin

Conditions
ConditionsYield
With pyridine; sodium hydroxide; dihydrogen peroxide
19484-74-3

7,8-Dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid

486-35-1

daphnetin

Conditions
ConditionsYield
With sodium hydrogensulfite anschliessend mit Schwefelsaeure erhitzen;
2445-80-9

7,8-dimethoxy-chromen-2-one

486-35-1

daphnetin

Conditions
ConditionsYield
With hydrogen iodide In acetic acid for 2h; Heating;20 mg
486-55-5

daphnin

A

2280-44-6

D-Glucose

B

486-35-1

daphnetin

Conditions
ConditionsYield
With hydrogenchloride

7,8-Dihydroxycoumarin Specification

The IUPAC name of 7,8-Dihydroxycoumarin is 7,8-dihydroxychromen-2-one. With the CAS registry number 486-35-1, it is also named as Daphnetin. The product's categories are Pharmaceutical Raw Materials; Coumarins. It is solid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.77; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 0.45; (5)ACD/BCF (pH 5.5): 2.22; (6)ACD/BCF (pH 7.4): 1.09; (7)ACD/KOC (pH 5.5): 61.44; (8)ACD/KOC (pH 7.4): 30.11; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.689; (14)Molar Refractivity: 43.52 cm3; (15)Molar Volume: 113.9 cm3; (16)Polarizability: 17.25×10-24cm3; (17)Surface Tension: 75.6 dyne/cm; (18)Enthalpy of Vaporization: 71.23 kJ/mol; (19)Vapour Pressure: 5.18E-08 mmHg at 25°C.

Preparation of 7,8-Dihydroxycoumarin: this chemical can be obtained by 7,8-dibenzyloxycoumarin. This reaction will need reagent AlBr3 and solvent nitrobenzene. The reaction time is 5 min. The yield is about 80%.

Uses of 7,8-Dihydroxycoumarin: it is used to produce 7,8-dibenzyloxycoumarin.  This reaction will need reagent K2CO3 and solvent nitrobenzene at the temperature of 60°C. The reaction time is 13 hour (s) and the yield is about 92%.

When you are using this chemical, please be cautious about it as the following:
It is not only toxic if swallowed, but also irritating to eyes, respiratory system and skin. So people shouold not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C/2Oc1c(O)c(O)ccc1\C=C\2
2. InChI: InChI=1/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
3. InChIKey: ATEFPOUAMCWAQS-UHFFFAOYAC

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 429mg/kg (429mg/kg)   Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.
mouse LD50 intravenous 375mg/kg (375mg/kg)   Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.
mouse LD50 oral 5370mg/kg (5370mg/kg)   Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.

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