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Basic Information
CAS No.: 1076-38-6
Name: 4-Hydroxycoumarin
Article Data: 105
Molecular Structure:
Molecular Structure of 1076-38-6 (4-Hydroxycoumarin)
Formula: C9H6O3
Molecular Weight: 162.145
Synonyms: 4-Hydroxy-2H-1-benzopyran-2-one;Benzotetronic acid;2H-1-Benzopyran-2-one,4-hydroxy-;Coumarin, 4-hydroxy-;4-Coumarinol;2-hydroxychromen-4-one;Coumarin, 4-hydroxy- (8CI);2H-1-Benzopyran-2-one, 4-hydroxy-;
EINECS: 214-060-2
Density: 1.446 g/cm3
Melting Point: 210-215 ºC
Boiling Point: 352.41 ºC at 760 mmHg
Flash Point: 165.353 ºC
Solubility: practically insoluble in water
Appearance: Yellow powder or chunks
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 50.44000
LogP: 1.49860
Synthetic route
201230-82-2

carbon monoxide

118-93-4

o-hydroxyacetophenone

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With selenium; 1,5-Diazabicyclo[5.4.0]undec-5-ene In tetrahydrofuran at 90℃;100%
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 100℃; under 22800 Torr; for 30h;100%
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 100℃; under 22800 Torr; for 30h; Mechanism; carbonylation of alkyl aryl ketones with CO using stoichiometric amount of Se, variation of temperature and solvent;100%
With triethylamine In tetrahydrofuran at 80℃; under 7355.08 Torr; for 4h;95%
With nitrobenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; selenium In tetrahydrofuran at 90℃; under 22800 Torr; for 30h; Mechanism; catalytic carbonylation of alkyl aryl ketones with CO by Se in the presence of oxidizing agent;68%
31005-07-9

4-allyloxy-2H-chromen-2-one

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With sodium hydrogen telluride; acetic acid In ethanol for 2h; Heating;99%
With ammonium formate; palladium on activated charcoal In methanol for 1.5h; Heating;95%
With iodine In dimethyl sulfoxide at 120℃; for 0.5h;78%
1821-20-1

ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water96%
118-93-4

o-hydroxyacetophenone

105-58-8

Diethyl carbonate

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With sodium hydride In toluene at 0℃; for 4.5h; Reflux;95%
With sodium hydride In toluene at 100℃; for 3h;85%
Stage #1: o-hydroxyacetophenone With sodium hydride In toluene; mineral oil
Stage #2: Diethyl carbonate In toluene; mineral oil Reflux;
Stage #3: With hydrogenchloride In water
85%
120450-94-4

2-oxo-2H-chromen-4-yl propionate

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With sodium hydrogen telluride In ethanol for 0.5h; Quantum yield; Heating; buffer: deoxygen. acetic acid;95%
14290-47-2

4-(piperidin-1-yl)-2H-chromen-2-one

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With hydrogenchloride for 0.5h; Product distribution; Heating;94%
66530-08-3

3-carbethoxy-4-hydroxycoumarin

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 100 - 105℃; for 1h; Hydrolysis; decarboxylation;90.5%
326925-91-1

3-acetyl-chroman-2,4-dione

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With sulfuric acid In ethanol; water for 1h; Deacetylation; Heating;90.2%
211449-34-2

N,N-diethyl-3-(2-hydroxyphenyl)-3-oxopropanamide

1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With trifluoroacetic acid In toluene for 1h; Heating;89%

C12H14BF2NO5S

A

1076-38-6

4-hydroxy[1]benzopyran-2-one

B

144224-85-1

3-(2-Hydroxy-phenyl)-N,N-dimethyl-3-oxo-propionamide

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 50℃; for 0.5h;A 7%
B 87%
With sodium hydrogencarbonate In acetonitrile at 50℃; for 1h;A 25%
B 66%
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Reported in EPA TSCA Inventory.

Specification

1.Introduction of  4-Hydroxycoumarin

The 4-Hydroxycoumarin, with the CAS NO of 1076-38-6, is a kind of White crystal. It has synonyms of 4-Hydroxy-2H-1-benzopyran-2-one;Benzotetronic acid;2H-1-Benzopyran-2-one,4-hydroxy-;Coumarin, 4-hydroxy-;4-Coumarinol;2-hydroxychromen-4-one;Coumarin, 4-hydroxy- (8CI) and 2H-1-Benzopyran-2-one, 4-hydroxy-. 4-Hydroxycoumarin should be stored in shady and cool warehouse and mainly used as pharmaceutical Intermediates.

2.Properties of 4-Hydroxycoumarin

(1) Nominal Mass: 162 Da  (2) Average Mass: 162.1421 Da  (3) Monoisotopic Mass: 162.031694 Da
(4) Index of Refraction: 1.66 (5) Molar Refractivity: 41.353 cm3  (6) Molar Volume: 112.076 cm3
(7) Surface Tension: 65.563 dyne/cm (8) Density: 1.447 g/cm3  (9) Flash Point: 165.353 °C
(10) Enthalpy of Vaporization: 63.022 kJ/mol  (11) Boiling Point: 352.41 °C at 760 mmHg  (12) Vapour Pressure: 0 mmHg at 25°C

3.Structure descriptors of 4-Hydroxycoumarin

IUPAC Name: 4-hydroxychromen-2-one

InChI: InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H

InChIKey: VXIXUWQIVKSKSA-UHFFFAOYSA-N

Canonical SMILES : C1=CC=C2C(=C1)C(=CC(=O)O2)O
 

4.Safety information of 4-Hydroxycoumarin

Hazard Codes: HarmfulXnIrritantXi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
WGK Germany: 3
RTECS: DJ3100000
Hazard Note: Irritant
 

5.Toxity information of 4-Hydroxycoumarin

 

1.    

orl-mus LD50:2 g/kg

    MPHEAE    Medicina et Pharmacologia Experimentalis. 17 (1967),497.
2.    

ipr-mus LD50:2000 mg/kg

    APTOA6    Acta Pharmacologica et Toxicologica. 2 (1946),109.
3.    

scu-mus LD50:750 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 128 (1960),126.

Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. When heated to decomposition it emits acrid smoke and fumes.