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525-82-6

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  • Manufacture supply bamboo extract Flavone 10% 30% 50% CAS NO 525-82-6

    Cas No: 525-82-6

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525-82-6 Usage

Chemical Properties

white crystalline powder

Uses

Flavone is a potentially useful biochemical for cytochrome P450 studies.

Definition

One of a group of flavonoid plant pigments existing as colorless needles, that are insoluble in water and melting at 100C. It fluoresces violet in concentrated sulfuric acid. It can be synthesized. Treatment with alcoholic alkali yields flavanone. The fla

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 689, 1957 DOI: 10.1021/ja01560a050The Journal of Organic Chemistry, 44, p. 497, 1979 DOI: 10.1021/jo01318a005Tetrahedron Letters, 31, p. 4073, 1990 DOI: 10.1016/S0040-4039(00)94503-9

Purification Methods

Dissolve it in dilute aqueous NaOH, filter and precipitate it by adding dilute (1:1) HCl. The process is repeated twice more, and the fluorescein is dried at 100o. Alternatively, it has been crystallised from acetone by allowing the solution to evaporate at 37o in an open beaker. It has also been recrystallised from EtOH and dried in a vacuum oven. [Beilstein 19 I 721, 19 II 248, 19 III/IV 2904, 19/8 V 456.]

Check Digit Verification of cas no

The CAS Registry Mumber 525-82-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 5 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 525-82:
(5*5)+(4*2)+(3*5)+(2*8)+(1*2)=66
66 % 10 = 6
So 525-82-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H

525-82-6 Well-known Company Product Price

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  • TCI America

  • (F0015)  Flavone  >98.0%(GC)

  • 525-82-6

  • 1g

  • 300.00CNY

  • Detail
  • TCI America

  • (F0015)  Flavone  >98.0%(GC)

  • 525-82-6

  • 5g

  • 630.00CNY

  • Detail
  • Alfa Aesar

  • (A13627)  Flavone, 99%   

  • 525-82-6

  • 1g

  • 225.0CNY

  • Detail
  • Alfa Aesar

  • (A13627)  Flavone, 99%   

  • 525-82-6

  • 5g

  • 753.0CNY

  • Detail
  • Alfa Aesar

  • (A13627)  Flavone, 99%   

  • 525-82-6

  • 25g

  • 3194.0CNY

  • Detail
  • Aldrich

  • (F2003)  Flavone  

  • 525-82-6

  • F2003-1G

  • 276.12CNY

  • Detail
  • Aldrich

  • (F2003)  Flavone  

  • 525-82-6

  • F2003-5G

  • 802.62CNY

  • Detail

525-82-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name flavone

1.2 Other means of identification

Product number -
Other names 2-PHENYLCHROMONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:525-82-6 SDS

525-82-6Synthetic route

1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione
1469-94-9

1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
copper dichloride In ethanol at 80℃; for 0.0833333h; microwave irradiation;98%
With potassium hydrogensulfate at 120℃; for 2h; Temperature; Green chemistry;98%
With gallium(III) triflate In nitromethane at 80℃; for 2h;97%
2-Iodophenol
533-58-4

2-Iodophenol

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With C22H28Br2N4Pd; diethylamine In N,N-dimethyl-formamide at 80℃; under 3000.3 Torr; for 24h; Autoclave;98%
With diethylamine In N,N-dimethyl-formamide at 100℃; under 10343.2 Torr; for 24h; Sonogashira Cross-Coupling; Autoclave;96%
With (trihexyl)(tetradecyl)phosphonium bromide; triethylamine; palladium dichloride at 110℃; under 760.051 Torr; for 24h; Autoclave;95%
benzaldehyde
100-52-7

benzaldehyde

1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium molybdate In hexan-1-ol at 70℃; for 3h;98%
Flavanone
487-26-3

Flavanone

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With pyrrolidone hydrotribromide In dimethyl sulfoxide at 80℃; for 2h;97%
With thallium(III) acetate In acetic acid for 3h; Heating;96%
With thallium(III) acetate In acetic acid for 3h; Heating;96%
(E)-2'-hydroxy-chalcone
888-12-0

(E)-2'-hydroxy-chalcone

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With indium(III) bromide; silica gel at 130 - 140℃; for 0.75h;96%
With iodine In dimethyl sulfoxide for 1h; Reflux;85%
With iodine In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 150℃; for 4h; Product distribution; Further Variations:; Solvents; Temperatures; reaction times;83%
1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one
16619-68-4

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 0 - 30℃; for 1.5h; Morita-Baylis-Hillman reaction; Inert atmosphere; regioselective reaction;96%
With thallium(III) toluene-p-sulfonate In methanol at 65℃; for 6h; Reagent/catalyst; Solvent; Time; regioselective reaction;91%
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Reagent/catalyst; Time; Temperature;90%
1-(2-hydroxyphenyl)-2-(triphenylphosphoranylidene)ethanone
81995-11-1

1-(2-hydroxyphenyl)-2-(triphenylphosphoranylidene)ethanone

benzoyl chloride
98-88-4

benzoyl chloride

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With pyridine In toluene for 5h; Heating;96%
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With Iodine monochloride; dimethyl sulfoxide at 50℃; for 0.5h; Temperature; Reagent/catalyst; Sonication; Green chemistry;96%
With cerium (IV) sulfate tetrahydrate; silica gel In neat (no solvent) at 100℃; for 4h; Concentration; Time; Green chemistry;94%
With copper(l) iodide; oxygen at 50℃; under 760.051 Torr; for 48h; oxa-Michael-oxidation; Ionic liquid;92%
1-[2-(tert-butyldimethylsilyloxy)phenyl]-3-phenylprop-2-yn-1-one
223511-19-1

1-[2-(tert-butyldimethylsilyloxy)phenyl]-3-phenylprop-2-yn-1-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With diethylamine In ethanol for 24h; Heating;96%
2'-allyloxychalcone
16619-51-5

2'-allyloxychalcone

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 120℃; for 0.5h; regioselective reaction;96%
Multi-step reaction with 2 steps
1: acetic acid / 24 h / 20 °C
2: iodine / dimethyl sulfoxide / 0.5 h / 130 °C
View Scheme
2,3-dihydro-4H-1-benzopyran-4-one
491-37-2

2,3-dihydro-4H-1-benzopyran-4-one

phenylboronic acid
98-80-6

phenylboronic acid

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen In dimethyl sulfoxide at 100℃; for 48h; Reagent/catalyst; Solvent;96%
1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one
16619-68-4

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

A

FLAVONE
525-82-6

FLAVONE

B

(Z)-4'-methoxyaurone
36685-41-3

(Z)-4'-methoxyaurone

Conditions
ConditionsYield
With silver nitrate In methanol Ambient temperature;A 5%
B 95%
1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one
16619-68-4

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

A

FLAVONE
525-82-6

FLAVONE

B

aurone
37542-14-6

aurone

Conditions
ConditionsYield
With silver nitrate In methanol Ambient temperature;A 5%
B 95%
With 2-pyridone sodium salt In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Solvent; Temperature; Time; regioselective reaction;A 3%
B 93%
With tricyclohexylphosphine In ethanol at 30℃; for 2h;A n/a
B 55%
1-(2-acetoxy-phenyl)-3-phenyl-2-propyn-1-one
16619-67-3

1-(2-acetoxy-phenyl)-3-phenyl-2-propyn-1-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With piperazine In acetonitrile at 25℃; for 3h; Schlenk technique;95%
With piperazine In acetonitrile at 20℃; for 6h; Schlenk technique;95%
With 18-crown-6 ether; potassium methanolate In tetrahydrofuran at 20℃; for 0.25h; Reagent/catalyst; Time; Temperature; Solvent;76%
iron pentacarbonyl
13463-40-6

iron pentacarbonyl

2-Iodophenol
533-58-4

2-Iodophenol

phenylacetylene
536-74-3

phenylacetylene

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With piperazine; palladium diacetate In acetonitrile at 50℃; for 12h; Schlenk technique;95%
2-phenylchromene
93514-42-2, 6053-99-2

2-phenylchromene

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(ll) bromide In decane; toluene at 80℃; for 0.0833333h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;94%
With thallium(III) nitrate In methanol Ambient temperature; overnight;20%
1-benzopyran-4(4H)-one
491-38-3

1-benzopyran-4(4H)-one

phenylboronic acid
98-80-6

phenylboronic acid

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
Stage #1: 1-benzopyran-4(4H)-one; phenylboronic acid With iron(III) trifluoromethanesulfonate; palladium diacetate; Trimethylacetic acid at 60℃; under air;
Stage #2: With potassium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone
94%
Stage #1: 1-benzopyran-4(4H)-one With 1,10-Phenanthroline; oxygen; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Heck type reaction;
Stage #2: phenylboronic acid In N,N-dimethyl-formamide at 100℃; for 24h; Heck type reaction; regioselective reaction;
86%
2,3-dihydro-4H-1-benzopyran-4-one
491-37-2

2,3-dihydro-4H-1-benzopyran-4-one

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen In dimethyl sulfoxide at 100℃; for 48h;93%
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen In dimethyl sulfoxide at 100℃; Heck Reaction;93%
2'-benzyloxy-2-bromo-acetophenone
36695-24-6

2'-benzyloxy-2-bromo-acetophenone

A

FLAVONE
525-82-6

FLAVONE

B

2-acetylphenyl benzoate
4010-33-7

2-acetylphenyl benzoate

Conditions
ConditionsYield
pyrex In benzene Irradiation;A 4%
B 92%
2-iodophenyl acetate
32865-61-5

2-iodophenyl acetate

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; thiourea; bis-triphenylphosphine-palladium(II) chloride; 1,3-bis-(diphenylphosphino)propane at 40℃; for 48h; Addition; cyclization;92%
3-iodo-2-phenyl-4H-1-benzopyran-4-one
98153-12-9

3-iodo-2-phenyl-4H-1-benzopyran-4-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With sodium formate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃;92%
With copper(l) iodide; potassium carbonate; isopropyl alcohol at 90℃; for 12h; Green chemistry; regioselective reaction;92%
4-oxo-2-phenyl-4H-chromen-6-yl 4-methylbenzenesulfonate
137527-18-5

4-oxo-2-phenyl-4H-chromen-6-yl 4-methylbenzenesulfonate

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With dimethylamine borane; potassium carbonate; triphenylphosphine; nickel In N,N-dimethyl-formamide at 120℃; for 12h;92%
3-bromo-2-phenyl-chromen-4-one
1025-86-1

3-bromo-2-phenyl-chromen-4-one

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; isopropyl alcohol at 90℃; for 12h; Catalytic behavior; Reagent/catalyst; Green chemistry; regioselective reaction;92%
trans-3-mesyloxyflavanone
67139-31-5

trans-3-mesyloxyflavanone

A

FLAVONE
525-82-6

FLAVONE

B

aurone
37542-14-6

aurone

Conditions
ConditionsYield
With dibutylamine In dimethyl sulfoxide for 72h; Ambient temperature;A 91.5%
B 6.2%
With sodium acetate In dimethyl sulfoxide at 25℃; for 144h;A 80.1%
B 10.9%
With sodium acetate In dimethyl sulfoxide at 25℃; for 144h; Product distribution; other reaction temperatures, solvents, reaction time, reagents, catalists, other amount of catalists and use other 3-mesyloxy-flavanone;A 80.1%
B 10.9%
With potassium cyanate; 18-crown-6 ether In benzene for 21h; Heating;A 31.3%
B 48%
With isopropylamine In dimethyl sulfoxide for 72h; Ambient temperature;A 57.5 % Spectr.
B 32.9 % Spectr.
1-(2-Hydroxy-4-methoxyphenyl)-3-phenylpropyn-1-one
98153-26-5

1-(2-Hydroxy-4-methoxyphenyl)-3-phenylpropyn-1-one

A

FLAVONE
525-82-6

FLAVONE

B

7-methoxoyflavone
22395-22-8

7-methoxoyflavone

Conditions
ConditionsYield
With silver nitrate In methanol Ambient temperature;A 91%
B n/a
3-<(4-Methylphenyl)sulphinyl>-4H-1-benzopyran-4-one
108378-93-4

3-<(4-Methylphenyl)sulphinyl>-4H-1-benzopyran-4-one

phenylmagnesium bromide

phenylmagnesium bromide

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78 - 0℃; for 2.5h;91%
1-(2'-bromophenyl)-3-phenylpropane-1,3-dione
36081-80-8

1-(2'-bromophenyl)-3-phenylpropane-1,3-dione

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Ullmann type reaction; under air;91%
With tert-butylisonitrile; palladium diacetate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 120℃; for 2h; Reagent/catalyst; Solvent; chemoselective reaction;86%
C18H16Br2O2
1657006-73-9

C18H16Br2O2

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; for 0.5h;91%
4-thioflavone
5465-04-3

4-thioflavone

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
With Clayfen for 0.025h; microwave irradiation;90%
With tetraethylammonium perchlorate; ethidium Bromide In N,N-dimethyl-formamide cathodic reduction;
With air In ethanol at 20℃; Photolysis;
2'-hydroxychalcone dichloride
75630-53-4

2'-hydroxychalcone dichloride

FLAVONE
525-82-6

FLAVONE

Conditions
ConditionsYield
at 210 - 220℃; for 1.5h;90%
FLAVONE
525-82-6

FLAVONE

1a,7a-Dihydro-1a-phenyl-7H-oxireno<1>benzopyran-7-one
134051-30-2

1a,7a-Dihydro-1a-phenyl-7H-oxireno<1>benzopyran-7-one

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0℃; for 36h;100%
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0℃; for 36h;100%
With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In acetonitrile at 0 - 1℃; for 1.25h;99%
FLAVONE
525-82-6

FLAVONE

2,2,2-trifluoroethyl acrylate
407-47-6

2,2,2-trifluoroethyl acrylate

2,2,2-trifluoroethyl (E)-3-(2-phenyl-4-oxo-4H-chromen-5-yl)acrylate

2,2,2-trifluoroethyl (E)-3-(2-phenyl-4-oxo-4H-chromen-5-yl)acrylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In tert-Amyl alcohol at 20 - 100℃; for 12.33h; Schlenk technique; Sealed tube; regioselective reaction;99%
Conditions
ConditionsYield
Stage #1: FLAVONE With Dimethylphenylsilane; C50H52N2; bis(pentafluorophenyl)borohydride In toluene at 20℃; for 1h; Inert atmosphere; Glovebox;
Stage #2: With trifluoroacetic acid In toluene at 20℃; for 0.166667h; Inert atmosphere; Glovebox; enantioselective reaction;
A n/a
B 99%
FLAVONE
525-82-6

FLAVONE

diethylstilbestrol
56-53-1

diethylstilbestrol

C18H20O2*2C15H10O2

C18H20O2*2C15H10O2

Conditions
ConditionsYield
In methanol at 20℃; Solvent;98.72%
FLAVONE
525-82-6

FLAVONE

3-chloro-2-phenyl-chromen-4-one
13178-98-8

3-chloro-2-phenyl-chromen-4-one

Conditions
ConditionsYield
With sulfuryl dichloride; Montmorillonite-K-10 clay In dichloromethane for 0.25h; Ambient temperature;98%
With pyridine; chloro-trimethyl-silane; [bis(acetoxy)iodo]benzene In dichloromethane at 0℃; for 3.5h;82%
With sulfuryl dichloride In tetrachloromethane63%
FLAVONE
525-82-6

FLAVONE

(2R*,2’R*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione
71840-34-1, 71840-35-2, 82908-23-4

(2R*,2’R*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran; methanol at -40℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; stereoselective reaction;98%
FLAVONE
525-82-6

FLAVONE

(2R*,2’S*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione
71840-35-2

(2R*,2’S*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran; methanol at 68℃; for 24h; Inert atmosphere; stereoselective reaction;98%
FLAVONE
525-82-6

FLAVONE

3-Mercapto-2-phenyl-4H-1-benzopyran-4-one
98153-13-0

3-Mercapto-2-phenyl-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sulfur; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.583333h;97%
Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen at 20℃; for 0.166667h; Kinetics; Reagent/catalyst; Time;97%
FLAVONE
525-82-6

FLAVONE

2-phenylchromanol

2-phenylchromanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 3h; Inert atmosphere;95%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

FLAVONE
525-82-6

FLAVONE

4-methyl-N-(4-oxo-2-phenyl-4H-chromen-5-yl)benzenesulfonamide
1607017-87-7

4-methyl-N-(4-oxo-2-phenyl-4H-chromen-5-yl)benzenesulfonamide

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 12h; Inert atmosphere;95%
FLAVONE
525-82-6

FLAVONE

3-(2-hydroxyphenyl)-5-phenyl-pyrazole
19726-12-6

3-(2-hydroxyphenyl)-5-phenyl-pyrazole

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 90℃;95%
N-methylmaleimide
930-88-1

N-methylmaleimide

FLAVONE
525-82-6

FLAVONE

1-methyl-3-(4-oxo-2-phenyl-4H-chromen-5-yl)pyrrolidine-2,5-dione

1-methyl-3-(4-oxo-2-phenyl-4H-chromen-5-yl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid In 1,2-dichloro-ethane at 80℃; for 20h; Sealed tube;94%

525-82-6Relevant articles and documents

Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution

Chang, Chao-Che,Chen, Chao-Tsen,Chou, Pi-Tai,Huang, Chun-Hao,Li, Elise Y.,Liao, Yu-Chan,Liu, Yi-Hung,Liu, Zong-Ying,Meng, Fan-Yi,Wang, Chun-Hsiang

supporting information, p. 12715 - 12724 (2021/08/30)

We report here, for the first time, the experimental observation on the excited-state intramolecular proton transfer (ESIPT) reaction of the thiol proton in room-temperature solution. This phenomenon is demonstrated by a derivative of 3-thiolflavone (3TF), namely, 2-(4-(diethylamino)phenyl)-3-mercapto-4H-chromen-4-one (3NTF), which possesses an - S - H···O= intramolecular H-bond (denoted by the dashed line) and has an S1 absorption at 383 nm. Upon photoexcitation, 3NTF exhibits a distinctly red emission maximized at 710 nm in cyclohexane with an anomalously large Stokes shift of 12 230 cm-1. Upon methylation on the thiol group, 3MeNTF, lacking the thiol proton, exhibits a normal Stokes-shifted emission at 472 nm. These, in combination with the computational approaches, lead to the conclusion of thiol-type ESIPT unambiguously. Further time-resolved study renders an unresolvable (180 fs) ESIPT rate for 3NTF, followed by a tautomer emission lifetime of 120 ps. In sharp contrast to 3NTF, both 3TF and 3-mercapto-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one (3FTF) are non-emissive. Detailed computational approaches indicate that all studied thiols undergo thermally favorable ESIPT. However, once forming the proton-transferred tautomer, the lone-pair electrons on the sulfur atom brings non-negligible nπ? contribution to the S1′ state (prime indicates the proton-transferred tautomer), for which the relaxation is dominated by the non-radiative deactivation. For 3NTF, the extension of π-electron delocalization by the diethylamino electron-donating group endows the S1′ state primarily in the ππ? configuration, exhibiting the prominent tautomer emission. The results open a new chapter in the field of ESIPT, covering the non-canonical sulfur intramolecular H-bond and its associated ESIPT at ambient temperature.

A novel one-pot synthesis of flavones

Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi

, p. 11655 - 11662 (2021/03/31)

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

METHOD FOR SYNTHESIZING (Z)-AURONE AND DERIVATIVE COMPOUNDS THEREOF

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Paragraph 0134-0135; 0140, (2021/05/11)

One embodiment of the present invention is described below. Provided is (Z)-operon comprising o - (alkanone -1 - yl) phenol or its derivative compound in a thallium (Tl) catalyst and an cyclization step for cyclizing the compound under an organic solvent, and a method for producing the derivative compound.

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