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Cas Database

91-64-5

91-64-5

Identification

  • Product Name:Coumarin

  • CAS Number: 91-64-5

  • EINECS:202-086-7

  • Molecular Weight:146.145

  • Molecular Formula: C9H6O2

  • HS Code:2932.21

  • Mol File:91-64-5.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H317 May cause an allergic skin reaction H331 Toxic if inhaled H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . SYMPTOMS: Exposure to this compound may cause narcosis. It may also cause irritation and liver damage. Absorption, Distribution and ExcretionA species difference has been reported for the excretion of an oral dose of (14)C-coumarin. Within 4 days rats excreted 47% of the label in the urine and 39% in the feces, whereas rabbits excreted 92% in the urine and negligible amount in the feces.

  • Fire-fighting measures: Suitable extinguishing media Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. This chemical is combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Carefully collect remainder. Then store and dispose of according to local regulations. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from food and feedstuffs.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Coumarin
  • Packaging:20mg
  • Price:$ 255
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  • Manufacture/Brand:TRC
  • Product Description:Coumarin
  • Packaging:1g
  • Price:$ 75
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Coumarin >99.0%(GC)
  • Packaging:500g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Coumarin >99.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Coumarin ≥99% (HPLC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Coumarin for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Coumarin ≥98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Coumarin ≥99% (HPLC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Coumarin Coumarin for synthesis. CAS 91-64-5, molar mass 146.14 g/mol., for synthesis
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Relevant articles and documentsAll total 224 Articles be found

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.

Visible-light-driven, photoredox-catalyzed cascade of ortho-hydroxycinnamic esters to access 3-fluoroalkylated coumarins

Song, Dan,Wang, Chao-Ming,Ye, Zhi-Peng,Xia, Peng-Ju,Deng, Zhi-Xiong,Xiao, Jun-An,Xiang, Hao-Yue,Yang, Hua

, p. 7480 - 7487 (2019)

A general and straightforward protocol for di-/perfluoroalkylation of ortho-hydroxycinnamic esters via a photoredox-catalyzed cascade was developed to access a variety of 3-fluoroalkylated coumarins. This method was characterized by all-in-one synthetic design, simplified operation, mild reaction conditions, and broad substrate scope. Moreover, a sequential one-pot procedure starting from commercially available salicylaldehyde was also successfully realized to synthesize 3-fluoroalkylated coumarins.

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.

Quantification of free coumarin and its liberation from glucosylated precursors by stable isotope dilution assays based on liquid chromatography-tandem mass spectrometry detection

Rychlik, Michael

, p. 796 - 801 (2008)

A stable isotope dilution assay for the quantification of free coumarin and glucosylated coumarin precursors has been developed using [13C 2]-coumarin as the internal standard. The doubly labeled coumarin was synthesized by reacting [13C2]-acetic anhydride with salicylic aldehyde and characterized by means of mass spectrometry and nuclear magnetic resonance (NMR) experiments. The specifity of liquid chromatography-tandem mass spectrometry enabled unequivocal determination and sensitive quantitation of the odorant. Because of the very simple extraction procedure, free coumarin could be analyzed within 1h. For quantification of total coumarin, the odorant was liberated from its precursors by an incubation with hydrochloric acid or β-glucosidase. In analyses of breakfast cereals, the intra-assay coefficient of variation was 9.9% (n = 5) for total coumarin. When coumarin was added to butter cookies at a level of 10 μg/kg, a recovery of 94.1% was found. Further addition studies revealed a detection limit of 2.9 μg/kg and a quantification limit of 8.6 μg/kg. Application of the stable isotope dilution assay to several plants, foods, and essential oils revealed high contents in cassia products and those foods in which cassia has been used as an ingredient. In contrast to this, Ceylon cinnamon contained much less coumarin. The odorant was also quantified in woodruff, clover seeds, and the essential oils of lavender, citron, and chamomile. Only trace amounts were detected in carrots and the essential oils of peppermint and dill, whereas in bilberries, black raspberries, and Angelica roots, coumarin was below detectable levels. In Ceylon cinnamon and cassia, the odorant occurred mainly in its free form, whereas in fenugreek seeds and woodruff, 68 and 88% of the total coumarin content was liberated from glucosylated precursors, respectively.

Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure

Hartman, Tomá?,Reisnerová, Martina,Chudoba, Josef,Svobodová, Eva,Archipowa, Nataliya,Kutta, Roger Jan,Cibulka, Radek

, p. 373 - 386 (2021/02/01)

Flavinium salts are frequently used in organocatalysis but their application in photoredox catalysis has not been systematically investigated to date. We synthesized a series of 5-ethyl-1,3-dimethylalloxazinium salts with different substituents in the positions 7 and 8 and investigated their application in light-dependent oxidative cycloelimination of cyclobutanes. Detailed mechanistic investigations with a coumarin dimer as a model substrate reveal that the reaction preferentially occurs via the triplet-born radical pair after electron transfer from the substrate to the triplet state of an alloxazinium salt. The very photostable 7,8-dimethoxy derivative is a superior catalyst with a sufficiently high oxidation power (E=2.26 V) allowing the conversion of various cyclobutanes (with Eox up to 2.05 V) in high yields. Even compounds such as all-trans dimethyl 3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate can be converted, whose opening requires a high activation energy due to a missing pre-activation caused by bulky adjacent substituents in cis-position.

Cyclobutane-cleavage of anti-head-to-head coumarin and quinolinone homo- and cross-dimers via single- and two-photon-absorption photochemistry

Bieniek, Nikolai,Inacker, Sebastian,Kim, Hee-Cheol,Hampp, Norbert

, (2021/04/19)

The light-driven cleavage of cyclobutane containing systems via [2 + 2] cycloreversion, such as di-coumarin, is an important yet poorly investigated photochemical reaction. Its applications can be found in smart crosslinking polymers or light-activated drug release. We report the increased cleavage efficiencies of the coumarins lactam analog quinolinone for single-photon as well as two-photon-absorption experiments. To investigate the structure-function relationship of the molecular substitution pattern and its influence on the photoactivity, a coumarin-quinolinone cross-dimer was synthesized and investigated towards its cleavage efficiencies in single-photon as well as two-photon photocleavage. The cross-dimer shows a lower cleavage efficiency than both homo-dimers. The presented results are of interest, e.g., for applications utilizing highly efficient cleavage reactions in symmetric or asymmetric molecular frameworks.

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.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 1611 - 1615 (2021/03/03)

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

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.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
at 493.7 ℃; Product distribution; Rate constant; thermal elimination;
2H-chromene
254-04-6

2H-chromene

1-benzopyran-4(4H)-one
491-38-3

1-benzopyran-4(4H)-one

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
With tert.-butylhydroperoxide; In ethyl acetate; at 40 ℃;
(Z)-(7S,10S,19S)-10-Benzyl-19-(4-hydroxy-benzyl)-7-isobutyl-7,8,10,11,13,14,16,17,19,20-decahydro-5-oxa-8,11,14,17,20-pentaaza-benzocyclohenicosene-6,9,12,15,18,21-hexaone

(Z)-(7S,10S,19S)-10-Benzyl-19-(4-hydroxy-benzyl)-7-isobutyl-7,8,10,11,13,14,16,17,19,20-decahydro-5-oxa-8,11,14,17,20-pentaaza-benzocyclohenicosene-6,9,12,15,18,21-hexaone

Leu-enkephalin
58822-25-6

Leu-enkephalin

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
rat liver homogenate; In water; dimethyl sulfoxide; at 37 ℃; for 6h; pH=7.4; Further Variations:; Catalysts; with esterase inhibitor; Enzyme kinetics;
(E)-3-(2-Hydroxy-phenyl)-N-[2-(4-hydroxy-phenyl)-ethyl]-acrylamide

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

tyrosamine
51-67-2

tyrosamine

coumarin
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;
100 % Spectr.
95%
C<sub>28</sub>H<sub>40</sub>N<sub>2</sub>O<sub>5</sub>Si<sub>2</sub>

C28H40N2O5Si2

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane
2469-55-8

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
In methanol; UV-irradiation;
(2aR*,8bS*)-1,1,2,2-tetramethyl-1,2,2a,8b-tetrahydro-3H-cyclobuta[c]chromen-3-one
7305-18-2,123411-46-1

(2aR*,8bS*)-1,1,2,2-tetramethyl-1,2,2a,8b-tetrahydro-3H-cyclobuta[c]chromen-3-one

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

2,3-Dimethyl-2-butene

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
With 5-ethyl-7,8-dimethoxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrobenzo[g]pteridin-5-ium perchlorate; In acetonitrile; at 20 ℃; for 1h; Reagent/catalyst; Overall yield = 57 percent; Irradiation; Inert atmosphere; Schlenk technique;
INDANE
496-11-7

INDANE

1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

coumarin
91-64-5

coumarin

inden-1-one
83-33-0

inden-1-one

Conditions
Conditions Yield
With N-hydroxyphthalimide; iron(III) oxide; oxygen; In acetonitrile; for 1h; under 760.051 Torr; Irradiation;
2-acetoxybenzaldehyde
5663-67-2

2-acetoxybenzaldehyde

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
With 4 A molecular sieve; 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl); In benzene; at 40 ℃; for 3h;
71%
coumarin-3-tert-butyl-peroxyester
850560-66-6

coumarin-3-tert-butyl-peroxyester

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

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

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
In [D3]acetonitrile; Further Variations:; Solvents; Product distribution; UV-irradiation;
69 % Chromat.
31 % Chromat.
salicylaldehyde
90-02-8

salicylaldehyde

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

2-triphenyl(α-carboxymethylene)phosphorane imidazolide

1H-imidazole
288-32-4

1H-imidazole

coumarin
91-64-5

coumarin

Conditions
Conditions Yield
salicylaldehyde; With sodium methylate; In 5,5-dimethyl-1,3-cyclohexadiene; at 60 ℃; for 2h; Inert atmosphere;
2-triphenyl(α-carboxymethylene)phosphorane imidazolide; In 5,5-dimethyl-1,3-cyclohexadiene; for 48h; Reflux; Inert atmosphere;
85%

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