Coumarin supplier | CasNO.91-64-5

Name
Coumarin
EINECS 202-086-7
CAS No. 91-64-5
Article Data299
CAS DataBase
Density 1.248 g/cm³
Solubility 1.7 g/L (20 ºC)
Melting Point 68-73 °C(lit.)
Formula C₉H₆O₂
Boiling Point 297.999 °C at 760 mmHg
Molecular Weight 146.145
Flash Point 118.268 °C
Transport Information UN 2811 6.1/PG 3
Appearance white crystals or crystalline powder
Safety 36/37-26
Risk Codes 20/21/22-36/37/38-40-43
Molecular Structure
Hazard Symbols Xi
Synonyms cis-o-Coumarinic acid lactone;2H-1-Benzopyran-2-one;Benzo-alpha-pyrone;Rattex;Coumarinic anhydride;5,6-Benzo-alpha-pyrone;2-Oxo-1,2-benzopyran;o-Hydroxycinnamic acid lactone;Benzo-a-pyrone;2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone;o-Coumaric acid lactone;2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone;5,6-Benzo-2-pyrone;1, 2-Benzopyrone;Cinnamic acid, o-hydroxy-, delta-lactone;Coumarine;2H-chromen-2-one;3-(2-Hydroxyphenyl)-2-propenoic delta-lactone;o-Hydroxycinnamic lactone;
PSA 30.21000
LogP 1.79300

Synthetic route

: 3986-98-9
2-thiocoumarin

: 91-64-5
coumarin

Conditions

Conditions	Yield
With sodium hydroxide; copper(l) chloride In water; acetonitrile at 25℃; for 0.25h;	100%
With di(n-butyl)tin oxide In 1,4-dioxane Heating;	97%
With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 24h;	83%
With hydrogenchloride; sodium nitrite In dichloromethane; water at 45℃; for 22h;	64%
With sodium carbonate; trifluoroacetic anhydride 1) CH2Cl2, r.t., 2 h; Yield given. Multistep reaction;

palladium-on-activated carbon: palladium-on-activated carbon

Pd-on-carbon Powder: Pd-on-carbon Powder

: 10407-33-7
methyl 3-(2-oxocyclohexyl)propionate

A: 91-64-5
coumarin

B: 119-84-6
C6H4(CH2CH2C(O)O)

Conditions

Conditions	Yield
In methyl 3-(2-oxcyclohexyl)propionate	A n/a B 100%

...Expand

: 3487-90-9
(E)-n-butyl 3-(2-hydroxyphenyl)acrylate

: 91-64-5
coumarin

Conditions

Conditions	Yield
In ethylene glycol at 200℃; for 12h;	99%

: 2-vinylphenyl acrylate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; for 24h;	99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;	70%
With Grubbs catalyst first generation In toluene at 80℃; for 2h; Inert atmosphere;
With Hoveyda-Grubbs catalyst second generation In chloroform-d1 at 25℃; for 24h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube; Darkness;	99 %Spectr.

: 108530-10-5
2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With methanol; zinc; Ni(Ph3P); 1,3-bis-(diphenylphosphino)propane; potassium iodide; zinc In N,N-dimethyl-formamide at 50℃; for 4h;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 60℃; for 2h;	82%

: 20883-98-1
methyl 2-coumarate

: 91-64-5
coumarin

Conditions

Conditions	Yield
In methanol at 40 - 50℃; for 14h; UV-irradiation;	96%
at 750℃;

: 5248-12-4
(α6aH,β6bH,β12bH,α12cH)-cyclobuta<1,2-c,4,3-c1>bis<1>benzopyran-6,7-dione

: 91-64-5
coumarin

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In acetonitrile at 25℃; for 0.333333h; Quantum yield; Mechanism; Irradiation;	96%
With 5-ethyl-1,3-dimethyl-8-(trifluoromethyl)alloxazinium perchlorate In acetonitrile at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Time; Irradiation; Inert atmosphere; Schlenk technique;	92%
With trifluorormethanesulfonic acid; riboflavine tetraacetate In acetonitrile at 20℃; for 0.166667h; Reagent/catalyst; Solvent; Irradiation; Schlenk technique; Inert atmosphere;	90%
In 1,4-dioxane for 0.266667h; Product distribution; Ambient temperature; Irradiation; correlation between photochemical fission and chemical structure;	25 % Chromat.
UV-irradiation;

: 33877-05-3
ethyl 3-(2-methoxyphenyl)acrylate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at 50℃; for 5h; Inert atmosphere;	96%

: 3,4-dibromochroman-2-one

: 91-64-5
coumarin

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Irradiation;	96%

: 119-84-6
C6H4(CH2CH2C(O)O)

: 91-64-5
coumarin

Conditions

Conditions	Yield
With dimethyl cis-but-2-ene-1,4-dioate at 200℃;	95%
Stage #1: C6H4(CH2CH2C(O)O) With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In fluorobenzene; dichloromethane Stage #2: With dichloro( 1,5-cyclooctadiene)platinum(ll); diallylcarbonate; silver trifluoroacetate In fluorobenzene; dichloromethane at 20℃; for 24h; Sealed tube; chemoselective reaction;	67%
With N,N’-di-tert-butylthiadiaziridine-1,1-dioxide; triphenylphosphine; copper(l) chloride at 65℃; for 20h; Inert atmosphere;	60%

: (E)-3-(2-Hydroxy-phenyl)-N-[2-(4-hydroxy-phenyl)-ethyl]-acrylamide

A: 51-67-2
tyrosamine

B: 91-64-5
coumarin

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Ambient temperature; Irradiation; other N-subsituted amides of o-hydroxy-trans-cinnamic acid;	A 95% B 100 % Spectr.

: 531-81-7
2-oxo-2H-chromene-3-carboxylic acid

: 91-64-5
coumarin

Conditions

Conditions	Yield
With pyridine for 5h; Heating;	95%
With acetic acid; silver carbonate In 2,4-dichlorophenoxyacetic acid dimethylamine at 100℃; for 16h;	63%
With copper(l) iodide; triethylamine In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 20h; Inert atmosphere; Schlenk technique;	57%
With bromobenzene; silver carbonate; palladium dichloride In dimethyl sulfoxide at 120℃; for 5h;
With dipotassium peroxodisulfate; silver(I) trifluoromethanethiolate; potassium carbonate In water; dimethyl sulfoxide at 110℃; for 24h; Solvent; Inert atmosphere; Sealed tube;	33 %Spectr.

: 3943-94-0, 17041-46-2, 6236-62-0
(E)-ethyl 2-hydroxycinnamate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;	94%
With tributylphosphine In methanol at 70℃; for 20h; Solvent; Reagent/catalyst; Inert atmosphere;	82%
With palladium on activated charcoal In dimethyl amine at 140℃; Sealed tube; Inert atmosphere;	78%
In benzene for 1h; Irradiation;	95 % Turnov.
With toluene-4-sulfonic acid In poly(methyl methacrylate) for 0.075h; Quantum yield; Reagent/catalyst; UV-irradiation; Darkness;

: 471-25-0
Propiolic acid

: 108-95-2
phenol

: 91-64-5
coumarin

Conditions

Conditions	Yield
With ytterbium(III) trifluoromethanesulfonate hydrate at 80℃; for 0.0333333h; Reagent/catalyst; Microwave irradiation;	93%
With trifluoroacetic acid In chlorobenzene at 100℃; for 1h; Inert atmosphere;	76%
With trifluorormethanesulfonic acid In chlorobenzene at 100℃; for 2h;	76%

: 151597-71-6
Acrylic acid ((E)-2-propenyl)-phenyl ester

: 91-64-5
coumarin

Conditions

Conditions	Yield
Stage #1: Acrylic acid ((E)-2-propenyl)-phenyl ester With titanium(IV) isopropylate In dichloromethane for 1h; Heating; Stage #2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 4h; ring closing metathesis; Heating;	93%

: 60998-71-2
phenyl prop-2-ynoate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With Echavarren's catalyst In dichloromethane at 18℃; for 1h;	93%
With gold(III) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 50℃;	84%

2-(1,1,1,1,1-pentacarbonyl-1-chroma)-2H-1-benzopyran: 2-(1,1,1,1,1-pentacarbonyl-1-chroma)-2H-1-benzopyran

: 91-64-5
coumarin

Conditions

Conditions	Yield
With pyridine N-oxide In dichloromethane at 23℃; for 3h;	93%

: 4279-77-0
S-phenyl hydrogen thiomalonate

: 90-02-8
salicylaldehyde

: 91-64-5
coumarin

Conditions

Conditions	Yield
With triethylamine; benzylamine In chloroform at 55℃; for 6h; Reagent/catalyst; Solvent;	93%

: 17831-88-8
4-chloro-2H-1-benzopyran-2-one

A: 91-64-5
coumarin

B: 118545-81-6
4,4'-bis-(2H-chromen-2-one)

Conditions

Conditions	Yield
With bis[2-(diphenylphosphino)phenyl] ether; potassium iodide; zinc; bis(triphenylphosphine)nickel(II) chloride In 1,4-dioxane at 130℃; for 0.5h; Ullmann-type reaction; microwave irradiation;	A n/a B 92%

: (3R*,4R*)-3,4-dibromo-3,4-dihydrocoumarin

: 91-64-5
coumarin

Conditions

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1,5-dimethoxynaphthalene; ascorbic acid In methanol; water for 5h; Inert atmosphere; Irradiation;	92%

: 957770-83-1
3-((4-fluorophenyl)thio)-3-oxopropanoic acid

: 90-02-8
salicylaldehyde

: 91-64-5
coumarin

Conditions

Conditions	Yield
With triethylamine; benzylamine In chloroform at 55℃; for 4h; Reagent/catalyst; Solvent;	92%

: 19754-56-4
n-butyl thiomalonate

: 90-02-8
salicylaldehyde

: 91-64-5
coumarin

Conditions

Conditions	Yield
With triethylamine; benzylamine In chloroform at 55℃; for 6h; Reagent/catalyst; Solvent;	92%

: 108-24-7
acetic anhydride

: 90-02-8
salicylaldehyde

: 91-64-5
coumarin

Conditions

Conditions	Yield
With polyphosphoric acid In N,N-dimethyl-formamide at 145℃; for 3h; Temperature; Solvent; Concentration; Time; Inert atmosphere;	91%
With polyphosphoric acid In N,N-dimethyl-formamide at 145℃; for 3h; Temperature; Inert atmosphere;	91%
With cesium acetate at 150 - 160℃; for 8h;	79%

: 90-02-8
salicylaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

A: 3943-94-0, 17041-46-2, 6236-62-0
(E)-ethyl 2-hydroxycinnamate

B: 91-64-5
coumarin

Conditions

Conditions	Yield
In toluene Heating;	A 91% B 4%
In xylene for 4h; Heating;	A 83% B 10%
for 4h; Heating;	A 82.8% B 9.6%

...Expand

: 77924-22-2
7-(1-Phenyl-1H-tetrazol-5-yloxy)-chromen-2-one

A: 5097-82-5
1-phenyl-5-hydroxytetrazole

B: 91-64-5
coumarin

C: 119-84-6
C6H4(CH2CH2C(O)O)

Conditions

Conditions	Yield
With sodium hypophosphite; palladium on activated charcoal In ethanol; water; benzene for 0.916667h; Heating;	A n/a B 91% C n/a
With sodium hypophosphite; palladium on activated charcoal In ethanol; benzene for 55h; Mechanism; Heating;	A n/a B 91% C n/a

...Expand

: 42974-18-5
3,4-dibromo-3,4-dihydrocoumarin

: 91-64-5
coumarin

Conditions

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.25h;	90%
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;	88%
With N,N,N,N,-tetramethylethylenediamine; sexithiophene In N,N-dimethyl-formamide for 2h; Inert atmosphere; Irradiation;	88%
In methanol at 20℃; for 6h; Irradiation;	65%

: 700-82-3
3,4,5,6,7,8-hexahydro-chromen-2-one

: 623-91-6
diethyl Fumarate

: 91-64-5
coumarin

Conditions

Conditions	Yield
palladium-carbon	90%

: 90-02-8
salicylaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 91-64-5
coumarin

Conditions

Conditions	Yield
With N,N-diethylaniline at 210 - 215℃; for 4h;	89.2%
With N,N-diethylaniline In xylene for 4h; Heating;	89%

: 91-64-5
coumarin

: 3986-98-9
2-thiocoumarin

Conditions

Conditions	Yield
With tetraphosphorus decasulfide In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Inert atmosphere; Reflux;	100%
With Lawessons reagent for 0.05h; microwave irradiation;	98%
With bis(tricyclohexyltin)sulfide; boron trichloride for 7h; Heating;	94%

: 91-64-5
coumarin

: 2725-81-7
6-nitrocoumarin

Conditions

Conditions	Yield
With sulfuric acid; nitric acid	100%
Stage #1: coumarin With sulfuric acid at 4℃; for 0.166667h; Stage #2: With guanidine nitrate	98%
With ammonium cerium(IV) nitrate; acetic acid at 20℃; for 2h;	92%

: 91-64-5
coumarin

: 119-84-6
C6H4(CH2CH2C(O)O)

Conditions

Conditions	Yield
With formic acid; palladium In methanol; water Ambient temperature;	100%
With hydrogen; W-2 Raney nickel In ethyl acetate for 0.833333h; Ambient temperature; Irradiation;	100%
With hydrogen; palladium on activated charcoal In acetic acid under 760.051 Torr; for 12h;	99%

: decacarbonyl-1κ(4)C,2κ(3)C,3κ(3)C-μ-hydrido-2:3κ(2)H-μ-hydroxy-2:3κ(2)O-trisosmium-(3 Os-Os)

: 91-64-5
coumarin

: Os3(CO)10(μ-H)(μ-OH)*coumarin

Conditions

Conditions	Yield
In hexane ligand was added to hexane soln. of Os-cluster in Schlenk tube, stirred for 100 min at room temp. under N2; solvent was removed under reduced pressure, recrystd. from CH2Cl2/hexaneat -5°C; elem. anal.;	99%

: 91-64-5
coumarin

: 116295-83-1
coumarin-d6

Conditions

Conditions	Yield
With 10% Pt/activated carbon; water-d2 In cyclohexane; isopropyl alcohol at 80℃; for 24h; Inert atmosphere;	99%

: 42201-84-3
1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene

: 91-64-5
coumarin

: 108-94-1
cyclohexanone

: ethyl 2-(3-(1-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-oxochroman-4-yl)acetate

Conditions

Conditions	Yield
Stage #1: 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene; coumarin With C18H14F18O15S6 In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: cyclohexanone In dichloromethane at -78℃; for 0.5h; Reagent/catalyst; Inert atmosphere;	99%

...Expand

: 91-64-5
coumarin

: 69-72-7
salicylic acid

: 2H,6H-pyrano<3,2-b>xanthene-2,6-dione

Conditions

Conditions	Yield
With ytterbium(III) trifluoromethanesulfonate nonohydrate In neat (no solvent) for 0.0833333h; Milling; Microwave irradiation;	98%

: 4721-98-6
6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline

: 91-64-5
coumarin

: (10RS,15aRS)-2,3-dimethoxy-9,10-dihydro-5H-10,15a methanobenzo[7,8][1,3]oxazocino[2,3-a]isoquinolin-8(6H)-one

Conditions

Conditions	Yield
With sodium carbonate In water at 80℃; for 16h; Solvent; Temperature; Reagent/catalyst; stereoselective reaction;	98%

: 131-58-8
2-Methylbenzophenone

: 91-64-5
coumarin

: 7-hydroxy-7-phenyl-6a,7,12,12a-tetrahydro-6H-naphtho[2,3-c]chromen-6-one

Conditions

Conditions	Yield
In toluene at 25℃; for 0.583333h; Concentration; Solvent; Time; Inert atmosphere; UV-irradiation; Flow reactor; diastereoselective reaction;	98%

: 1666-13-3
diphenyl diselenide

: 91-64-5
coumarin

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

Conditions

Conditions	Yield
With trimethylsilylazide; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h; Solvent; Reagent/catalyst;	98%
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1h; Reagent/catalyst; Solvent; regioselective reaction;	95%

: 69447-36-5
bis(2-methylphenyl) diselenide

: 91-64-5
coumarin

: 3-(o-tolylselanyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1.5h; regioselective reaction;	98%

: 63930-16-5
1,2-bis(3-fluorophenyl)diselane

: 91-64-5
coumarin

: 3-((3-fluorophenyl)selanyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; regioselective reaction;	98%

: 21856-94-0
di-p-tolyl diselenide

: 91-64-5
coumarin

: 3-(p-tolylselanyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1h; regioselective reaction;	98%

: 563-79-1
2,3-Dimethyl-2-butene

: 91-64-5
coumarin

: 7305-18-2
1,1,2,2-tetramethyl-2,2adihydro-1H-cyclobuta[c]chromen-3(8bH)-one

Conditions

Conditions	Yield
With aluminum tri-bromide In dichloromethane; 1,2-dibromomethane at 20℃; for 5h; Inert atmosphere; Irradiation;	97%

: 91-64-5
coumarin

: 98-80-6
phenylboronic acid

: 15185-05-4
4-phenylcoumarin

Conditions

Conditions	Yield
With 5-Nitro-1,10-phenanthroline; oxygen; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 24h; Heck reaction; chemoselective reaction;	97%
With 1,10-Phenanthroline; oxygen In N,N-dimethyl-formamide at 100℃; for 24h; Catalytic behavior; Solvent; Suzuki Coupling; Sealed tube; regioselective reaction;	87%
With 1,10-Phenanthroline; oxygen; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Sealed tube;	82%
With 5-Nitro-1,10-phenanthroline; oxygen; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 12h; Schlenk technique; Sealed tube;	60%
Stage #1: coumarin With 1,10-Phenanthroline; oxygen; palladium diacetate In acetonitrile for 0.0833333h; Heck type reaction; Stage #2: phenylboronic acid In N,N-dimethyl-formamide at 100℃; Heck type reaction; regioselective reaction;	14%

: 42201-84-3
1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene

: 91-64-5
coumarin

: 67-64-1
acetone

: ethyl 2-(3-(2-((tert-butyldimethylsilyl)oxy)propan-2-yl)-2-oxochroman-4-yl)acetate

Conditions

Conditions	Yield
Stage #1: 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene; coumarin With C18H14F18O15S6 In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: acetone In dichloromethane at -78℃; for 0.5h; Inert atmosphere;	97%

...Expand

: 127-19-5
N,N-dimethyl acetamide

: 91-64-5
coumarin

: N-methyl-N-((2-oxo-2H-chromen-3-yl)methyl)acetamide

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; di-tert-butyl peroxide at 120℃; for 6h;	97%
With di-tert-butyl peroxide; potassium iodide at 120℃; for 20h; Sealed tube;	77%

: 64-17-5
ethanol

: 91-64-5
coumarin

: 20921-04-4
ethyl 3-(2-hydroxyphenyl)propanoate

Conditions

Conditions	Yield
With (BQ‑NCOP)IrHCl; sodium t-butanolate at 60℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	97%

: 91806-16-5
1,9-dimethyl-3,4-dihydro-β-carboline

: 91-64-5
coumarin

: (5RS,15bRS)-15-methyl-5,6,9,10-tetrahydro-5,15b-methanobenzo[7',8'][1,3]oxazocino-[3',2':1,2]pyrido[3,4-b]indol-7(15H)-one

Conditions

Conditions	Yield
With sodium carbonate In water at 80℃; for 20h; stereoselective reaction;	97%

: 2923-18-4
sodium 2,2,2-trifluoroacetate

: 91-64-5
coumarin

: 3-((trifluoromethyl)thio)-2H-chromen-2-one

Conditions

Conditions	Yield
With iron(III) chloride; sulfur In ethanol at 60℃; for 2h; Sealed tube;	97%

: 20541-48-4
1,2-bis(4-bromophenyl)diselenide

: 91-64-5
coumarin

: 3-((4-bromophenyl)selanyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1.5h;	97%
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1.5h; regioselective reaction;	97%

Coumarin Consensus Reports

Coumarin(91-64-5) is reported in EPA TSCA Inventory.

Coumarin Specification

The CAS registry number of Coumarin is 91-64-5. The systematic name is 2H-chromen-2-one. In addition, it is a fragrant chemical compound of benzopyrone found in many plants with the molecular formula C₉H₆O₂. What's more, it has a sweet odor, and readily recognised as the scent of newly-mown hay. So it can be used in perfumes.

Physical properties about this chemical are: (1)ACD/LogP: 1.39; (2)ACD/LogD (pH 5.5): 1.39; (3)ACD/LogD (pH 7.4): 1.39; (4)ACD/BCF (pH 5.5): 6.705; (5)ACD/BCF (pH 7.4): 6.705; (6)ACD/KOC (pH 5.5): 135.881; (7)ACD/KOC (pH 7.4): 135.881; (8)#H bond acceptors: 2; (9)Polar Surface Area: 26.3 Å²; (10)Index of Refraction: 1.595; (11)Molar Refractivity: 39.767 cm³; (12)Molar Volume: 117.097 cm³; (13)Polarizability: 15.765 ×10^-24cm³; (14)Surface Tension: 46.411 dyne/cm; (15)Density: 1.248 g/cm³; (16)Flash Point: 118.268 °C; (17)Enthalpy of Vaporization: 53.789 kJ/mol; (18)Boiling Point: 297.999 °C at 760 mmHg; (19)Vapour Pressure: 0.001 mmHg at 25°C.

Preparation of Coumarin: it can be prepared in a laboratory in a Perkin reaction between salicylaldehyde and acetic anhydride. The reaction needs solvent potassium carbonate and the temperature should be controlled at 210-212 °C. After the reaction, via a series of washing, vacuum distillation and recrystallization by ethanol you can get the desired product.

Coumarin can be prepared in a laboratory in a Perkin reaction between salicylaldehyde and acetic anhydride

Uses of Coumarin: It has been used as aroma enhancer in pipe tobaccos and certain alcoholic drinks. And it is used in the pharmaceutical industry as a precursor molecule in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol. In addition, it is also used as a gain medium in some dye lasers, and as a sensitizer in older photovoltaic technologies. Moreover, it can be used to get chromene-2-thione. This reaction will need reagent bis(1,5-cyclooctanediylboryl) sulfide and solvent heptane. The reaction time is 2 hours by heating. The yield is about 80%.

Coumarin can be used to get chromene-2-thione

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In addition, it may cause sensitization by skin contact and is moderately toxic to the liver and kidneys. When you are using it, wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc2c(c1)ccc(=O)o2
(2)Std. InChI: InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
(3)Std. InChIKey: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	202mg/kg (202mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: OTHER CHANGES	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
man	TDLo	oral	87mg/kg/17W-I (87mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED	Human Toxicology. Vol. 8, Pg. 501, 1989.
mouse	LD50	intraperitoneal	220mg/kg (220mg/kg)	BEHAVIORAL: ANALGESIA	Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 897, 1965.
mouse	LD50	oral	196mg/kg (196mg/kg)		Yakugaku Zasshi. Journal of Pharmacy. Vol. 83, Pg. 1124, 1963.
mouse	LD50	subcutaneous	242mg/kg (242mg/kg)		Yakugaku Zasshi. Journal of Pharmacy. Vol. 83, Pg. 1124, 1963.
rat	LD50	oral	293mg/kg (293mg/kg)		Food and Cosmetics Toxicology. Vol. 12, Pg. 385, 1974.
women	TDLo	oral	30mg/kg/30D-I (30mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED	Human Toxicology. Vol. 8, Pg. 501, 1989.

Product Name

Coumarin

Synthetic route

Coumarin Consensus Reports

Coumarin Specification

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