Name: Coumarin
SKU: 91-64-5

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Basic Information

Molecular Structure:
CAS No.:	91-64-5
Name:	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:	Xi
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

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%

Raw Materials

Downstream Products

69-72-7

271-89-6

939-19-5

51690-26-7

495-78-3

93-35-6

64-19-7

2555-28-4

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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.

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Consensus Reports

Specification