7-Methoxycoumarin supplier

Name
7-Methoxycoumarin
EINECS 208-513-3
CAS No. 531-59-9
Article Data110
CAS DataBase
Density 1.249 g/cm³
Solubility MISCIBLE
Melting Point 117-121 °C(lit.)
Formula C₁₀H₈O₃
Boiling Point 335.3 °C at 760 mmHg
Molecular Weight 176.172
Flash Point 138.6 °C
Transport Information
Appearance Beige powder.
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Herniarin (6CI);Umbelliferone, methyl ether (6CI);7-Methoxychromen-2-one;Ayapanin;Methylumbelliferone;
PSA 39.44000
LogP 1.80160

Synthetic route

: 93-35-6
7-hydroxy-2H-chromen-2-one

halomethane: halomethane

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 1h;	99%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 3-bromophenyltrimethylammonium iodide

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 3h; Solvent;	99%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 762-42-5
dimethyl acetylenedicarboxylate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In neat (no solvent) at 100℃; for 0.0666667h; Microwave irradiation; Green chemistry;	98%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 74-88-4
methyl iodide

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	97%
With potassium carbonate In acetone at 25℃; for 5h; Inert atmosphere;	97%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;	94%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With N,N-diethylaniline at 215℃; for 0.25h;	95.2%
With N,N-diethylaniline at 215℃; for 0.25h; Heating;	95%
With N,N-diethylaniline at 215℃; for 0.25h; Product distribution; Mechanism; other solvent, other temperature; other salicylaldehydes;	95.2%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 77-78-1
dimethyl sulfate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
Stage #1: 7-hydroxy-2H-chromen-2-one With potassium hydroxide In acetonitrile for 0.5h; Stage #2: dimethyl sulfate In acetonitrile at 40℃; for 48h;	95%
With potassium carbonate; potassium iodide In acetone at 20℃; for 5h;	90.2%
With potassium carbonate In acetone for 0.05h; Etherification; methylation; microwave irradiation;	85%
With potassium carbonate In acetone for 72h; Reflux;	80%
With potassium carbonate; benzene

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 616-38-6
carbonic acid dimethyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.025h; microwave irradiation;	95%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 35616-23-0
N,N,N,2-tetramethylbenzenaminium iodide

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 3h;	94%

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 121-45-9
phosphorous acid trimethyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With boron trifluoride In diethyl ether for 0.0152778h; microwave irradiation;	93%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 4279-77-0
S-phenyl hydrogen thiomalonate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With triethylamine; benzylamine In chloroform at 55℃; for 3h;	92%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

A: 531-59-9
7-methoxycoumarin

B: 139386-27-9
ethyl 3-(2-hydroxy-4-methoxyphenyl)-(E)-2-propenoate

Conditions

Conditions	Yield
In benzene at 80℃; for 4h; Heating;	A 7% B 91%
In benzene for 4h; Heating;	A 7.4% B 90.7%

...Expand

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 105-39-5
chloroacetic acid ethyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With molecular sieve; sodium methylate; triphenylphosphine Wittig reaction; microwave irradiation;	89%
With sodium methylate; magnesium oxide; triphenylphosphine Wittig reaction;	87%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 96-34-4
methyl chloroacetate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With sodium methylate; triphenylphosphine at 80 - 210℃; for 5.5h; Ionic liquid;	89%

: 5451-83-2
acetic acid 3-methoxyphenyl ester

: 292638-85-8
acrylic acid methyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With formic acid; rhodium(II) acetate dimer; sodium acetate In neat (no solvent) at 100℃; for 3h; Molecular sieve; Inert atmosphere; regioselective reaction;	88%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 21204-67-1
methyl (triphenylphosphoranylidene)acetate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
In toluene at 220℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube;	86%
With N,N-diethylaniline at 210℃; for 2h; Wittig Olefination;	71%
With 7-hydroxy-2H-chromen-2-one In N,N-diethylaniline at 210℃; for 2h; Wittig reaction;	60%

: 74-83-9
methyl bromide

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
Stage #1: 7-hydroxy-2H-chromen-2-one With potassium carbonate In acetone for 0.25h; Inert atmosphere; Reflux; Stage #2: methyl bromide In acetone Inert atmosphere; Reflux;	86%
With potassium carbonate In acetone at 80℃; for 1h;
In acetone at 80℃; for 1h; Williamson Ether Synthesis;

: 93198-68-6
(E)-methyl 2’-hydroxy-4’-methoxycinnamate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With tributylphosphine In methanol at 70℃; for 20h; Inert atmosphere;	83%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 96-34-4
methyl chloroacetate

A: 531-59-9
7-methoxycoumarin

B: 93198-68-6
(E)-methyl 2’-hydroxy-4’-methoxycinnamate

Conditions

Conditions	Yield
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; sodium methylate at 110℃; for 0.166667h; Horner-Wadsworth-Emmons olefination; Ionic liquid; Microwave irradiation;	A 81% B 19%

...Expand

: 150-19-6
O-methylresorcine

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With PPA at 70℃; for 4h;	80%

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With naphthalene-1,4-dicarbonitrile; oxygen In water; acetonitrile for 6h; Irradiation;	80%
With naphthalene-1,4-dicarbonitrile; oxygen In acetonitrile for 6h; Mechanism; Irradiation; variation of substituents;	80%
Multi-step reaction with 2 steps 1: riboflavin; oxygen / acetonitrile; methanol / 20 °C / UV-irradiation 2: riboflavin; oxygen / acetonitrile; methanol / 20 °C / UV-irradiation View Scheme

: 150-19-6
O-methylresorcine

: 617-48-1
malic acid

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With pyridine; sulfuric acid at 119℃; for 0.05h; Microwave irradiation;	79%

: 907584-68-3
acrylic acid 5-methoxy-2-vinyl-phenyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;	78%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 108-24-7
acetic anhydride

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With sodium acetate In N,N-dimethyl-formamide at 180℃; for 6h; Inert atmosphere;	78%
With sodium acetate at 185℃; for 6h; Inert atmosphere;
With sodium acetate at 170℃; for 6h; Inert atmosphere; Sealed tube;
With sodium acetate at 185℃; for 6h; Inert atmosphere;

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 73818-41-4
2-triphenyl(α-carboxymethylene)phosphorane imidazolide

A: 288-32-4
1H-imidazole

B: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
Stage #1: 2-Hydroxy-4-methoxybenzaldehyde With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere; Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;	A n/a B 72%

...Expand

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

carbethoxymethylenetriphenylphosphorane: carbethoxymethylenetriphenylphosphorane

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
at 210 - 215℃; for 5h;	71%

: 616-47-7
1-methyl-1H-imidazole

: 93-35-6
7-hydroxy-2H-chromen-2-one

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With Di-tert-butyl acetylenedicarboxylate In neat (no solvent) at 100℃; for 0.0833333h; Microwave irradiation; Green chemistry;	70%

: 2067-86-9
8-formyl-7-hydroxycoumarin

: 77-78-1
dimethyl sulfate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 8.5h;	70%

: 1123745-75-4
3-methoxyphenyl propiolate

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With Echavarren's catalyst In dichloromethane at 18℃; for 1h;	70%

: 63604-94-4
2-bromo-5-methoxyphenol

: 292638-85-8
acrylic acid methyl ester

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With palladium diacetate; potassium hydrogencarbonate at 140℃; for 0.366667h; Heck reaction; Microwave irradiation; neat (no solvent);	69%

: C11H12O4

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
In methanol at 40 - 50℃; for 23h; UV-irradiation;	69%

: 531-59-9
7-methoxycoumarin

: 72167-80-7
3-bromo-7-methoxy-2H-chromen-2-one

Conditions

Conditions	Yield
With N-chloro-succinimide; copper(II) chloride monohydrate; zinc(II) chloride In acetonitrile at 82℃; for 0.0833333h; regioselective reaction;	99.5%
With N-Bromosuccinimide; sodium acetate In acetonitrile Inert atmosphere;	95%
With N-Bromosuccinimide; sodium acetate In acetonitrile at 20℃;	91%

: 531-59-9
7-methoxycoumarin

: 93-35-6
7-hydroxy-2H-chromen-2-one

Conditions

Conditions	Yield
With Pyridine hydrobromide In sulfolane at 150 - 160℃; for 7h; Inert atmosphere;	98%
With aluminum (III) chloride In toluene for 3h; Reflux;	86%
With 1-n-butyl-3-methylimidazolim bromide; toluene-4-sulfonic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 115℃; for 13h;	80%

: 531-59-9
7-methoxycoumarin

: 1666-13-3
diphenyl diselenide

: 7-methoxy-3-(phenylselanyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h; regioselective reaction;	97%

: 531-59-9
7-methoxycoumarin

: 20921-02-2
7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one

Conditions

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating;	96%
palladium-carbon	96%
With hydrogen; Lindlar's catalyst In ethanol at 55℃; under 51754.1 Torr; for 18h;

: 531-59-9
7-methoxycoumarin

: 117139-04-5
3-chloro-7-methoxy-2H-chromen-2-one

Conditions

Conditions	Yield
With N-chloro-succinimide; copper(II) chloride monohydrate; zinc(II) chloride In acetonitrile at 82℃; for 1h; regioselective reaction;	95.3%

: 67-56-1
methanol

: 531-59-9
7-methoxycoumarin

: 93198-68-6
(E)-methyl 2’-hydroxy-4’-methoxycinnamate

Conditions

Conditions	Yield
With sodium methylate for 5h; Heating;	93%
With sodium methylate Heating;	92%
With sodium methylate for 5h; Heating;	92%
With sodium methylate for 3h; Heating;	88%
With sodium methylate

: 531-59-9
7-methoxycoumarin

: 124-41-4
sodium methylate

: C11H12O4

Conditions

Conditions	Yield
In methanol for 4.5h; Inert atmosphere; Reflux;	93%

: 67-56-1
methanol

: 531-59-9
7-methoxycoumarin

Conditions

Conditions	Yield
With sodium methylate for 4.5h; Reflux;	93%

: 531-59-9
7-methoxycoumarin

: 124-41-4
sodium methylate

: 93198-68-6
(E)-methyl 2’-hydroxy-4’-methoxycinnamate

Conditions

Conditions	Yield
In methanol for 5h; Heating;	92%

: 531-59-9
7-methoxycoumarin

: 50585-10-9, 86211-76-9
3-methyl-2-butenyllithium

: 155689-02-4
4-(1,1-Dimethyl-allyl)-7-methoxy-chroman-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran 1.) -78 deg C, 1.5 h; 2.) warm up to 0 deg C, 30 min;	91%

1-bromo-4-methoxy-benzene: 1-bromo-4-methoxy-benzene

: 531-59-9
7-methoxycoumarin

: 25439-60-5
2,3-bis(4-methoxyphenyl)-6-methoxy-1-benzofuran

Conditions

Conditions	Yield
With 1,10-Phenanthroline; palladium diacetate; caesium carbonate In 1,3,5-trimethyl-benzene at 160℃; for 18h;	91%

: 531-59-9
7-methoxycoumarin

: 353-83-3
1,1,1-trifluoro-2-iodoethane

: 7-methoxy-3-(2,2,2-trifluoroethyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); potassium carbonate In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Irradiation; Inert atmosphere;	91%

: 531-59-9
7-methoxycoumarin

: 37786-10-0
7-methoxycoumarin syn head-to-tail dimer

Conditions

Conditions	Yield
In solid Irradiation;	90%
for 15h; Ambient temperature; Irradiation;	90%
In water for 5h; Irradiation; micelles of sodium dodecyl sulfate (SDS) (0.032 M);	70%

: 531-59-9
7-methoxycoumarin

: 37786-10-0, 95839-59-1, 138808-82-9, 138808-83-0
3,9-Dimethoxy-6a,6b,12a,12b-tetrahydro-5,11-dioxa-dibenzo[a,b]biphenylene-6,12-dione

Conditions

Conditions	Yield
Irradiation;	90%
With sodium dodecyl-sulfate 1.) 15 to 20 h, room temperature 2.) 5 h, irradiation; Yield given. Multistep reaction;

: 531-59-9
7-methoxycoumarin

: 95839-59-1
(6aS,6bS,12aR,12bR)-3,9-Dimethoxy-6a,6b,12a,12b-tetrahydro-5,11-dioxa-dibenzo[a,b]biphenylene-6,12-dione

Conditions

Conditions	Yield
for 15h; Irradiation;	90%

: 531-59-9
7-methoxycoumarin

: 84379-72-6
1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate

: 3-(tert-butyl)-7-methoxy-2H-chromen-2-one

Conditions

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;	90%
With tris[2-phenylpyridinato-C2,N]iridium(III); trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere; Irradiation; Green chemistry;	75%

: 531-59-9
7-methoxycoumarin

: 103-19-5
di(p-tolyl) disulfide

: 7-methoxy-3-(p-tolylthio)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h; regioselective reaction;	89%

7-Methoxycoumarin Chemical Properties

Empirical Formula: C₁₀H₈O₃
Molecular Weight: 176.1687
EINECS: 208-513-3
Index of Refraction: 1.572
Density: 1.248 g/cm³
Flash Point: 138.6 °C
Enthalpy of Vaporization: 57.84 kJ/mol
Boiling Point: 335.3 °C at 760 mmHg
Vapour Pressure: 0.000121 mmHg at 25 °C
Melting point: 117-121 °C(lit.)
Water solubility: Miscible
Appearance: Beige to salmon-pinkish powder
Solubility: DMF: soluble
Product categories of 7-Methoxycoumarin (CAS NO.531-59-9)): Coumarins
Structure of 7-Methoxycoumarin (CAS NO.531-59-9):

7-Methoxycoumarin Toxicity Data With Reference

1.		orl-rat LD50:4300 mg/kg		FCTOD7 Food and Chemical Toxicology. 26 (1988),375.
2.		skn-gpg LD50:>5 g/kg		FCTOD7 Food and Chemical Toxicology. 26 (1988),375.

Carcinogenicity of Acenaphthenequinone (CAS NO.82-86-0) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. You can see actual entry in RTECS for complete information.

7-Methoxycoumarin Consensus Reports

Reported in EPA TSCA Inventory.

7-Methoxycoumarin Safety Profile

Slightly toxic by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

7-Methoxycoumarin Specification

7-Methoxycoumarin ,its cas register number is 531-59-9. It also can be called Herniarin ; 2H-1-benzopyran-2-one, 7-methoxy- ; 7-Méthoxy-2H-chromén-2-one and 7-Methoxy-2H-chromen-2-on . It is hazardous,so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly,Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While ,it's Inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.
In addition, Acenaphthenequinone (CAS NO.82-86-0) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon dioxide, carbon monoxide.

Product Name

7-Methoxycoumarin

Synthetic route

7-Methoxycoumarin Chemical Properties

7-Methoxycoumarin Toxicity Data With Reference

7-Methoxycoumarin Consensus Reports

7-Methoxycoumarin Safety Profile

7-Methoxycoumarin Specification

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