Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium molybdate In hexan-1-ol at 70℃; for 3h; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
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
benzoyl chloride
FLAVONE
Conditions | Yield |
---|---|
With pyridine In toluene for 5h; Heating; | 96% |
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
With diethylamine In ethanol for 24h; Heating; | 96% |
2'-allyloxychalcone
FLAVONE
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
A
FLAVONE
B
(Z)-4'-methoxyaurone
Conditions | Yield |
---|---|
With silver nitrate In methanol Ambient temperature; | A 5% B 95% |
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With piperazine; palladium diacetate In acetonitrile at 50℃; for 12h; Schlenk technique; | 95% |
2-phenylchromene
FLAVONE
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
FLAVONE
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
pyrex In benzene Irradiation; | A 4% B 92% |
2-iodophenyl acetate
carbon monoxide
phenylacetylene
FLAVONE
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
With dimethylamine borane; potassium carbonate; triphenylphosphine; nickel In N,N-dimethyl-formamide at 120℃; for 12h; | 92% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; isopropyl alcohol at 90℃; for 12h; Catalytic behavior; Reagent/catalyst; Green chemistry; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
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
A
FLAVONE
B
7-methoxoyflavone
Conditions | Yield |
---|---|
With silver nitrate In methanol Ambient temperature; | A 91% B n/a |
3-<(4-Methylphenyl)sulphinyl>-4H-1-benzopyran-4-one
FLAVONE
Conditions | Yield |
---|---|
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78 - 0℃; for 2.5h; | 91% |
1-(2'-bromophenyl)-3-phenylpropane-1,3-dione
FLAVONE
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide at 130℃; for 0.5h; | 91% |
Conditions | Yield |
---|---|
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
FLAVONE
Conditions | Yield |
---|---|
at 210 - 220℃; for 1.5h; | 90% |
FLAVONE
1a,7a-Dihydro-1a-phenyl-7H-oxireno<1>benzopyran-7-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
FLAVONE
A
(2S)-flavanone
B
(R)-flavanone
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In methanol at 20℃; Solvent; | 98.72% |
FLAVONE
3-chloro-2-phenyl-chromen-4-one
Conditions | Yield |
---|---|
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 tetrachloromethane | 63% |
FLAVONE
(2R*,2’R*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran; methanol at -40℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; stereoselective reaction; | 98% |
FLAVONE
(2R*,2’S*)-2,2’-diphenyl-[2,2’-bichromane]-4,4’-dione
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran; methanol at 68℃; for 24h; Inert atmosphere; stereoselective reaction; | 98% |
FLAVONE
3-Mercapto-2-phenyl-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
With sulfur; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.583333h; | 97% |
FLAVONE
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen at 20℃; for 0.166667h; Kinetics; Reagent/catalyst; Time; | 97% |
FLAVONE
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 3h; Inert atmosphere; | 95% |
4-toluenesulfonyl azide
FLAVONE
4-methyl-N-(4-oxo-2-phenyl-4H-chromen-5-yl)benzenesulfonamide
Conditions | Yield |
---|---|
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
3-(2-hydroxyphenyl)-5-phenyl-pyrazole
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 90℃; | 95% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid In 1,2-dichloro-ethane at 80℃; for 20h; Sealed tube; | 94% |
Synonyms :2-Phenyl-4H-1-benzopyran-4-one; 2-Phenylchromone
MF: C15H10O2
MW: 222.24
EINECS: 208-383-8
2-PHENYLCHROMONE(525-82-6),its melting point is about 94-97 °C(lit.),boiling point is 185 °C / 1mmHg .
Following is the molecular structure of 2-PHENYLCHROMONE(525-82-6):
1. | dni-hmn:fbr 100 mg/L | BCPCA6 Biochemical Pharmacology. 33 (1984),3823. | ||
2. | orl-mus LD50:2500 mg/kg | JHTCAO Journal of Heterocyclic Chemistry. 21 (1984),193. | ||
3. | ipr-mus LD50:380 mg/kg | FRPSAX Farmaco, Edizione Scientifica. 13 (1958),561. | ||
4. | scu-mus LD >400 mg/kg | ANTCAO Antibiotics and Chemotherapy. 3 (1953),603. |
Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Other safty informations about 2-PHENYLCHROMONE(525-82-6):
Hazard Codes: Xi (Irritant)
Risk Statements
R 36/37/38 (Irritating to eyes, respiratory system and skin )
Safety Statements :
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36 :Wear suitable protective clothing
WGK Germany : 2
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