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91-64-5

Basic Information
CAS No.: 91-64-5
Name: Coumarin
Article Data: 299
Molecular Structure:
Molecular Structure of 91-64-5 (Coumarin)
Formula: C9H6O2
Molecular Weight: 146.145
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;
EINECS: 202-086-7
Density: 1.248 g/cm3
Melting Point: 68-73 °C(lit.)
Boiling Point: 297.999 °C at 760 mmHg
Flash Point: 118.268 °C
Solubility: 1.7 g/L (20 ºC)
Appearance: white crystals or crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 20/21/22-36/37/38-40-43
Safety: 36/37-26
Transport Information: UN 2811 6.1/PG 3
PSA: 30.21000
LogP: 1.79300
Synthetic route
3986-98-9

2-thiocoumarin

91-64-5

coumarin

Conditions
ConditionsYield
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
ConditionsYield
In methyl 3-(2-oxcyclohexyl)propionateA n/a
B 100%
3487-90-9

(E)-n-butyl 3-(2-hydroxyphenyl)acrylate

91-64-5

coumarin

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

2-vinylphenyl acrylate

91-64-5

coumarin

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

3,4-dibromochroman-2-one

91-64-5

coumarin

Conditions
ConditionsYield
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
ConditionsYield
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%
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Consensus Reports

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

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.