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91-64-5 Usage

Description

Coumarin is a naturally occurring Benzopyrone compound that is found in a large number of plants belonging to many different families, including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is also found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs. Coumarin is a colorless crystalline compound with a pleasant odor, used in making perfumes. It has a sweet, fresh, hay-like, odor similar to vanilla seeds, and a burning taste with a bitter undertone and nut-like flavor on dilution.

Uses

Used in Flavor and Fragrance Industry:
Coumarin is used as a spice for the preparation of floral fragrances such as lavender, rosemary, and sweet clover. It is used in perfumes, cosmetics, soaps, and detergents as a flavoring agent for blending fragrances to make the aroma lasting and unchanged.
Used in Electroplating Industry:
Coumarin is used as an electroplating additive to prevent the occurrence of pores in coating and can increase the brightness.
Used in Printing and Plastic Industry:
Coumarin is used as the flavor enhancer of printing ink and plastic.
Used in Pharmaceutical Industry:
Coumarin is considered a blood thinner, and it can also increase blood flow. Some sources cite anti-oxidant capacities as well. It is used as a pharmaceutical aid (flavor) and has anti-neoplastic, anti-inflammatory, and anti-hyperglycemic properties.
Used in Laser Technology:
Coumarin, as a laser dye, has an output laser range within the blue-green region (420 ~ 570nm) and has high fluorescence quantum efficiency, such as 7-ethylamino-6-methyl-4-trifluoromethyl coumarin Lactone 307.
Note: Coumarin was formerly used as spices and cigarettes spices but was banned from 1977. Since then, China had also prohibited its application in food.

Brief Introduction

It is also known as 1, 2-benzopyrone, cis ortho-caberillin, o-hydroxy cinnamon lactone and coumarin. It is contained in many natural plants in the form of glycosides and esters as vanillin instead of free-form. Coumarin will come out when certain plants are fermented and processed. Coumarin is found in the seeds of Dayton beans (Riccinechoides) in 1820 and is widely distributed in the plant kingdom, especially in plant species including Umbelliferae, Soybean, Rutaceae and Calyx. Seeds contain about 1.5% of the coumarin. In addition, coumarin is also contained in lavender oil, cinnamon oil and Peru balsam. Coumarin is spicy with sweet and lemongrass aroma. The aroma is emitted from the pink gum in the leaves of the fragrant beans, and the gum is made from the breakdown of the coumarin glycosides in the leaves. The aroma emitted by Sweet alfalfa is actually from the release of coumarin due to fermentation and decomposition during the stacking process. Precipitate from the ether appears as orthorhombic white pyramid or oblique sheet-like crystals with Lemongrass-type smell. It can subject to sublimation.

Preparation

Coumarin is currently produced by Perkin synthesis from salicylaldehyde. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperature.A process for the production of coumarin from hexahydrocoumarin by dehydrogenation has also been elaborated.Since the odor of coumarin is relatively weak, strong-smelling by-products (e.g., vinylphenol) must be removed. Many purification methods have been reported and patented.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 4704, 1962 DOI: 10.1021/jo01059a541Tetrahedron Letters, 27, p. 3911, 1986 DOI: 10.1016/S0040-4039(00)83914-3

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Coumarin is sensitive to exposure to light. Coumarin is also sensitive to heat. Coumarin is incompatible with strong acids, strong bases and oxidizers. Coumarin is hydrolyzed by hot concentrated alkalis. Coumarin can be halogenated, nitrated and hydrogenated (in the presence of catalysts).

Hazard

Toxic by ingestion; carcinogenic. Use in food products prohibited (FDA). Questionable carcinogen.

Health Hazard

SYMPTOMS: Exposure to Coumarin may cause narcosis. It may also cause irritation and liver damage.

Fire Hazard

Coumarin is combustible.

Flammability and Explosibility

Nonflammable

Biological Activity

Oral anticoagulants can be prepared from compounds with coumarin as a base. Coumarin has been known for well over a century and, in addition to its use pharmaceutically, it is also an excellent odor-enhancing agent. However, because of its toxicity, it is not permitted in food products in the United States (Food and Drug Administration). One commercial drug is 3-(alpha-acetonyl-4-nitrobenzyl)- 4-hydroxycoumarin. This drug reduces the concentration of prothrombin in the blood and increases the prothrombin time by inhibiting the formation of prothrombin in the liver. The drug also interferes with the production of factors VII, IX, and X, so that their concentration in the blood is lowered during therapy. The inhibition of prothrombin involves interference with the action of vitamin K, and it has been postulated that the drug competes with vitamin K for an enzyme essential for prothrombin synthesis. Another commercial drug is bis-hydroxy-coumarin, C19H12O6. The actions of this drug are similar to those just described.

Contact allergens

Coumarin is an aromatic lactone naturally occurring in Tonka beans and other plants. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU

Safety Profile

Poison by ingestion, intraperitoneal, and subcutaneous routes. Questionable carcinogen with experimental tumorigenic data. Experimental teratogenic effects. Mutation data reported. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and fumes. See also KETONES and ANHYDRIDES.

Synthesis

May be extracted from tonka beans; from salicylaldehyde and acetic anhydride in the presence of sodium acetate; also from o-cresol and carbonyl chloride followed by chlorination of the carbonate and fusion with a mixture of alkali acetate, acetic anhydride and a catalyst.

Environmental Fate

Coumarin toxicity is a function of blood and target tissue levels of coumarin relative to the metabolic capacity of the target organ. Cellular toxicity results when the formation of the toxic moieties exceeds the capacity of the cell to detoxify. This can have significant impact when comparing dosing by gavage to dietary exposure.

Purification Methods

Coumarin crystallises from ethanol or water and sublimes in vacuo at 43o [Srinivasan & deLevie J Phys Chem 91 2904 1987]. [Beilstein 17/10 V 143.]

Toxicity evaluation

Coumarin is readily biodegradable. Coumarin is unlikely to bind to soil. Coumarin does not bioaccumulate; the bioconcentration factor has been determined to be <10–40. Various environmental fate studies have shown that coumarin in the environment would biodegrade and be lost to volatilization. Losses resulting from photolysis may also occur.

Check Digit Verification of cas no

The CAS Registry Mumber 91-64-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 91-64:
(4*9)+(3*1)+(2*6)+(1*4)=55
55 % 10 = 5
So 91-64-5 is a valid CAS Registry Number.

91-64-5 Well-known Company Product Price

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  • TCI America

  • (C0395)  Coumarin  >99.0%(GC)

  • 91-64-5

  • 25g

  • 160.00CNY

  • Detail
  • TCI America

  • (C0395)  Coumarin  >99.0%(GC)

  • 91-64-5

  • 500g

  • 810.00CNY

  • Detail
  • Alfa Aesar

  • (A15336)  Coumarin, 98%   

  • 91-64-5

  • 250g

  • 506.0CNY

  • Detail
  • Alfa Aesar

  • (A15336)  Coumarin, 98%   

  • 91-64-5

  • 1000g

  • 972.0CNY

  • Detail
  • Alfa Aesar

  • (A15336)  Coumarin, 98%   

  • 91-64-5

  • 5000g

  • 3525.0CNY

  • Detail
  • Sigma-Aldrich

  • (01260595)  Coumarin  primary pharmaceutical reference standard

  • 91-64-5

  • 01260595-50MG

  • 2,545.92CNY

  • Detail
  • Sigma-Aldrich

  • (72609)  Coumarin  certified reference material, TraceCERT®

  • 91-64-5

  • 72609-100MG

  • 968.76CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000438)  Coumarin  European Pharmacopoeia (EP) Reference Standard

  • 91-64-5

  • Y0000438

  • 1,880.19CNY

  • Detail

91-64-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name coumarin

1.2 Other means of identification

Product number -
Other names Kumarin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Odor agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:91-64-5 SDS

91-64-5Synthetic route

2-thiocoumarin
3986-98-9

2-thiocoumarin

coumarin
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

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

methyl 3-(2-oxocyclohexyl)propionate

A

coumarin
91-64-5

coumarin

B

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

C6H4(CH2CH2C(O)O)

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

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

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
In ethylene glycol at 200℃; for 12h;99%
2-vinylphenyl acrylate

2-vinylphenyl acrylate

coumarin
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.
2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate
108530-10-5

2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate

coumarin
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%
methyl 2-coumarate
20883-98-1

methyl 2-coumarate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
In methanol at 40 - 50℃; for 14h; UV-irradiation;96%
at 750℃;
(α6aH,β6bH,β12bH,α12cH)-cyclobuta<1,2-c,4,3-c1>bis<1>benzopyran-6,7-dione
5248-12-4

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

coumarin
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;
ethyl 3-(2-methoxyphenyl)acrylate
33877-05-3

ethyl 3-(2-methoxyphenyl)acrylate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 50℃; for 5h; Inert atmosphere;96%
3,4-dibromochroman-2-one

3,4-dibromochroman-2-one

coumarin
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%
C6H4(CH2CH2C(O)O)
119-84-6

C6H4(CH2CH2C(O)O)

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

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

A

tyrosamine
51-67-2

tyrosamine

B

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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.
2-oxo-2H-chromene-3-carboxylic acid
531-81-7

2-oxo-2H-chromene-3-carboxylic acid

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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.
(E)-ethyl 2-hydroxycinnamate
3943-94-0, 17041-46-2, 6236-62-0

(E)-ethyl 2-hydroxycinnamate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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;
Propiolic acid
471-25-0

Propiolic acid

phenol
108-95-2

phenol

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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%
Acrylic acid ((E)-2-propenyl)-phenyl ester
151597-71-6

Acrylic acid ((E)-2-propenyl)-phenyl ester

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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%
phenyl prop-2-ynoate
60998-71-2

phenyl prop-2-ynoate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With pyridine N-oxide In dichloromethane at 23℃; for 3h;93%
S-phenyl hydrogen thiomalonate
4279-77-0

S-phenyl hydrogen thiomalonate

salicylaldehyde
90-02-8

salicylaldehyde

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With triethylamine; benzylamine In chloroform at 55℃; for 6h; Reagent/catalyst; Solvent;93%
4-chloro-2H-1-benzopyran-2-one
17831-88-8

4-chloro-2H-1-benzopyran-2-one

A

coumarin
91-64-5

coumarin

B

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

4,4'-bis-(2H-chromen-2-one)

Conditions
ConditionsYield
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

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

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1,5-dimethoxynaphthalene; ascorbic acid In methanol; water for 5h; Inert atmosphere; Irradiation;92%
3-((4-fluorophenyl)thio)-3-oxopropanoic acid
957770-83-1

3-((4-fluorophenyl)thio)-3-oxopropanoic acid

salicylaldehyde
90-02-8

salicylaldehyde

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With triethylamine; benzylamine In chloroform at 55℃; for 4h; Reagent/catalyst; Solvent;92%
n-butyl thiomalonate
19754-56-4

n-butyl thiomalonate

salicylaldehyde
90-02-8

salicylaldehyde

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With triethylamine; benzylamine In chloroform at 55℃; for 6h; Reagent/catalyst; Solvent;92%
acetic anhydride
108-24-7

acetic anhydride

salicylaldehyde
90-02-8

salicylaldehyde

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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%
salicylaldehyde
90-02-8

salicylaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

A

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

(E)-ethyl 2-hydroxycinnamate

B

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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%
7-(1-Phenyl-1H-tetrazol-5-yloxy)-chromen-2-one
77924-22-2

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

A

1-phenyl-5-hydroxytetrazole
5097-82-5

1-phenyl-5-hydroxytetrazole

B

coumarin
91-64-5

coumarin

C

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

C6H4(CH2CH2C(O)O)

Conditions
ConditionsYield
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
3,4-dibromo-3,4-dihydrocoumarin
42974-18-5

3,4-dibromo-3,4-dihydrocoumarin

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
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%
3,4,5,6,7,8-hexahydro-chromen-2-one
700-82-3

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

diethyl Fumarate
623-91-6

diethyl Fumarate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
palladium-carbon90%
salicylaldehyde
90-02-8

salicylaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
With N,N-diethylaniline at 210 - 215℃; for 4h;89.2%
With N,N-diethylaniline In xylene for 4h; Heating;89%
coumarin
91-64-5

coumarin

2-thiocoumarin
3986-98-9

2-thiocoumarin

Conditions
ConditionsYield
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%
coumarin
91-64-5

coumarin

6-nitrocoumarin
2725-81-7

6-nitrocoumarin

Conditions
ConditionsYield
With sulfuric acid; nitric acid100%
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%
coumarin
91-64-5

coumarin

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

C6H4(CH2CH2C(O)O)

Conditions
ConditionsYield
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)

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)

coumarin
91-64-5

coumarin

Os3(CO)10(μ-H)(μ-OH)*coumarin

Os3(CO)10(μ-H)(μ-OH)*coumarin

Conditions
ConditionsYield
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%
coumarin
91-64-5

coumarin

coumarin-d6
116295-83-1

coumarin-d6

Conditions
ConditionsYield
With 10% Pt/activated carbon; water-d2 In cyclohexane; isopropyl alcohol at 80℃; for 24h; Inert atmosphere;99%
1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene
42201-84-3

1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene

coumarin
91-64-5

coumarin

cyclohexanone
108-94-1

cyclohexanone

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

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

Conditions
ConditionsYield
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%
coumarin
91-64-5

coumarin

salicylic acid
69-72-7

salicylic acid

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

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

Conditions
ConditionsYield
With ytterbium(III) trifluoromethanesulfonate nonohydrate In neat (no solvent) for 0.0833333h; Milling; Microwave irradiation;98%
6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline
4721-98-6

6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline

coumarin
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

(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
ConditionsYield
With sodium carbonate In water at 80℃; for 16h; Solvent; Temperature; Reagent/catalyst; stereoselective reaction;98%
2-Methylbenzophenone
131-58-8

2-Methylbenzophenone

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
In toluene at 25℃; for 0.583333h; Concentration; Solvent; Time; Inert atmosphere; UV-irradiation; Flow reactor; diastereoselective reaction;98%
diphenyl diselenide
1666-13-3

diphenyl diselenide

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
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%
bis(2-methylphenyl) diselenide
69447-36-5

bis(2-methylphenyl) diselenide

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1.5h; regioselective reaction;98%
1,2-bis(3-fluorophenyl)diselane
63930-16-5

1,2-bis(3-fluorophenyl)diselane

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; regioselective reaction;98%
di-p-tolyl diselenide
21856-94-0

di-p-tolyl diselenide

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 1h; regioselective reaction;98%
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
With aluminum tri-bromide In dichloromethane; 1,2-dibromomethane at 20℃; for 5h; Inert atmosphere; Irradiation;97%
coumarin
91-64-5

coumarin

phenylboronic acid
98-80-6

phenylboronic acid

4-phenylcoumarin
15185-05-4

4-phenylcoumarin

Conditions
ConditionsYield
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%
1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene
42201-84-3

1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene

coumarin
91-64-5

coumarin

acetone
67-64-1

acetone

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

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

Conditions
ConditionsYield
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%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
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%
ethanol
64-17-5

ethanol

coumarin
91-64-5

coumarin

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

ethyl 3-(2-hydroxyphenyl)propanoate

Conditions
ConditionsYield
With (BQ‑NCOP)IrHCl; sodium t-butanolate at 60℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;97%
1,9-dimethyl-3,4-dihydro-β-carboline
91806-16-5

1,9-dimethyl-3,4-dihydro-β-carboline

coumarin
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

(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
ConditionsYield
With sodium carbonate In water at 80℃; for 20h; stereoselective reaction;97%
sodium 2,2,2-trifluoroacetate
2923-18-4

sodium 2,2,2-trifluoroacetate

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
With iron(III) chloride; sulfur In ethanol at 60℃; for 2h; Sealed tube;97%
1,2-bis(4-bromophenyl)diselenide
20541-48-4

1,2-bis(4-bromophenyl)diselenide

coumarin
91-64-5

coumarin

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

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

Conditions
ConditionsYield
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%

91-64-5Relevant articles and documents

Two-photon-induced cycloreversion reaction of coumarin photodimers

Kim,Kreiling,Greiner,Hampp

, p. 899 - 903 (2003)

Photochemical reactions induced by two-photon-absorption processes offer several advantages over common one-photon initiated photoreactions, e.g., three-dimensional spatial control. We present the photocleavage reaction of coumarin photodimers via a two-photon process using pulsed frequency-doubled Nd:YAG-laser light. The two-photon-induced cycloreversion reaction leads selectively to the cleavage of the coumarin photodimers resulting in the formation of monomeric coumarin molecules. The two-photon cross section of the coumarin photodimer was determined to be of 1.6×10-52 cm4 s photon-1. The presented reaction is of interest, e.g., for the photo-triggered release of chemicals in areas which cannot be directly optically addressed due to cover layers which have a high absorption at the single-photon-absorption wavelength.

The Copper-Catalyzed Reaction of 2-(1-Hydroxyprop-2-yn-1-yl)phenols with Sulfonyl Azides Leading to C3-Unsubstituted N-Sulfonyl-2-iminocoumarins

Zhao, Yu,Zhou, Zitong,Liu, Lvling,Chen, Man,Yang, Weiguang,Chen, Qi,Gardiner, Michael G.,Banwell, Martin G.

, p. 9155 - 9162 (2021)

An operationally simple synthesis of Z-configured and C3-unsubstituted N-sulfonyl-2-iminocoumarins (e.g., 8a) that proceeds under mild conditions is achieved by reacting 2-(1-hydroxyprop-2-yn-1-yl)phenols (e.g., 6a) with sulfonyl azides (e.g., 7a). The cascade process involved likely starts with a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. This is followed by ring-opening of the resulting metalated triazole (with accompanying loss of nitrogen), reaction of the ensuing ketenimine with the pendant phenolic hydroxyl group, and finally dehydration of the (Z)-N-(4-hydroxychroman-2-ylidene)sulfonamide so formed.

Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism

Huang, Lin,Bismuto, Alessandro,Rath, Simon A.,Trapp, Nils,Morandi, Bill

supporting information, p. 7290 - 7296 (2021/03/01)

The direct dehydrogenation of alkanes is among the most efficient ways to access valuable alkene products. Although several catalysts have been designed to promote this transformation, they have unfortunately found limited applications in fine chemical synthesis. Here, we report a conceptually novel strategy for the catalytic, intermolecular dehydrogenation of alkanes using a ruthenium catalyst. The combination of a redox-active ligand and a sterically hindered aryl radical intermediate has unleashed this novel strategy. Importantly, mechanistic investigations have been performed to provide a conceptual framework for the further development of this new catalytic dehydrogenation system.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

Zhou, Min-Jie,Zhang, Lei,Liu, Guixia,Xu, Chen,Huang, Zheng

supporting information, p. 16470 - 16485 (2021/10/20)

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions

?tv?s, Sándor B.,Fül?p, Ferenc,Kónya, Zoltán,Kukovecz, ákos,Márton, András,Mészáros, Rebeka,Pálinkó, István,Szabados, Márton,Varga, Gábor

, p. 4685 - 4696 (2021/07/12)

Herein, we report novel catalytic methodologies for protodecarboxylations and decarboxylative deuterations of carboxylic acids utilizing a silver-containing hybrid material as a heterogeneous noble metal catalyst. After an initial batch method development, a chemically intensified continuous flow process was established in a simple packed-bed system which enabled gram-scale protodecarboxlyations without detectable structural degradation of the catalyst. The scope and applicability of the batch and flow processes were demonstrated through decarboxylations of a diverse set of aromatic carboxylic acids. Catalytic decarboxylative deuterations were achieved on the basis of the reaction conditions developed for the protodecarboxylations using D2O as a readily available deuterium source.

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