Conditions | Yield |
---|---|
With sodium perborate In acetic acid for 1.5h; steam bath; | 100% |
With (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)); oxygen; pivalaldehyde In acetonitrile for 2h; Ambient temperature; | 98% |
With thionyl chloride for 2h; Heating; | 91% |
Conditions | Yield |
---|---|
With aluminum oxide; potassium permanganate In 1,2-dichloro-ethane for 118h; Product distribution; Ambient temperature; other reagent, reaction time; | 100% |
With potassium hydroxide; 18-crown-6 ether; oxygen In 1,2-dimethoxyethane at 20℃; for 1h; | 100% |
With aluminum oxide; potassium permanganate; water In 1,2-dichloro-ethane for 118h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; chlorobenzene In toluene at 105℃; for 12h; | 100% |
With potassium osmate(VI) dihydrate; potassium carbonate; potassium hexacyanoferrate(III) In water; acetonitrile at 60℃; for 0.5h; chemoselective reaction; | 100% |
With chromium(VI) oxide; methyl-tridecylammonium chloride; sodium perborate In water; benzene at 60℃; for 24h; | 99% |
methanol
4',4'-dimethyl-3'-phenylfluorene-9-spiro-2'-oxazolidin-5'-one
9-fluorenone
Conditions | Yield |
---|---|
With sulfuric acid for 8h; Heating; other characteristic reaction (with hydroxylamine); | 100% |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; silver nitrate In water; acetonitrile Ambient temperature; | 100% |
With hydrogenchloride; dihydrogen peroxide In methanol Ambient temperature; | 98% |
With t-butyl bromide; dimethyl sulfoxide at 70 - 75℃; for 24h; | 95% |
9-fluorenone triphenylphosphazine
A
9-fluorenone
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With oxygen; methylene blue In dichloromethane at -78℃; for 0.0833333h; Irradiation; other reagent; | A 100% B n/a |
With oxygen; methylene blue In dichloromethane Quantum yield; Irradiation; |
fluoren-9-one-dibenzyldithioacetal
A
dibenzyl disulphide
B
9-fluorenone
Conditions | Yield |
---|---|
With tert-butylhypochlorite In tetrachloromethane for 1h; Ambient temperature; other reagent; | A n/a B 100% |
Conditions | Yield |
---|---|
With cesium pivalate; palladium(0)bis(tricyclohexylphosphine) In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 7h; Carbonylation; cyclization; | 100% |
With tristricyclohexylphosphine palladium(0); cesium pivalate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 7h; | 100% |
With palladium diacetate; sodium carbonate; magnesium sulfate; tricyclohexylphosphine tetrafluoroborate; Trimethylacetic acid In toluene at 110℃; under 760.051 Torr; for 25h; Sealed tube; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With cesium pivalate; palladium(0)bis(tricyclohexylphosphine) In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 7h; Carbonylation; cyclization; | 100% |
With tristricyclohexylphosphine palladium(0); cesium pivalate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 7h; | 100% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 48h; Reagent/catalyst; Inert atmosphere; | 58% |
With 1,10-Phenanthroline; palladium diacetate In 1,2-dichloro-ethane at 120℃; under 760.051 Torr; for 8h; | 5% |
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2-dimethylpropanoic anhydride; 1,2-bis-(diphenylphosphino)ethane; potassium iodide at 160℃; for 0.5h; Wavelength; Reagent/catalyst; Inert atmosphere; Microwave irradiation; Sealed tube; | 98% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2-dimethylpropanoic anhydride; 1,2-bis-(diphenylphosphino)ethane at 160℃; for 20h; Reagent/catalyst; Temperature; Inert atmosphere; | 97% |
With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In 1,2-dichloro-ethane at 25℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.25h; Heating; | 98% |
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.25h; Oxidation; Heating; | 98% |
With water; oxygen In acetonitrile at 60℃; under 760.051 Torr; for 2h; Autoclave; Green chemistry; | 98% |
4'-cyano-3'-phenyl-4'-t-butylfluorene-9-spiro-2'-oxazolidin-5'-one
9-fluorenone
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 8h; Heating; | 98% |
dispiro[9H-fluorene-9,3'-(1,2,4,5-tetroxane)-6',9''-[9H]fluorene]
A
6H-benzo[c]chromen-6-one
B
9-fluorenone
Conditions | Yield |
---|---|
With antimonypentachloride at 20℃; for 0.666667h; Product distribution; other reagent, time; | A 98% B 90% |
With antimonypentachloride In dichloromethane at 20℃; for 0.666667h; | A 98% B 90% |
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate In dichloromethane for 0.5h; Ambient temperature; | 98% |
With 3-carboxypyridinium chlorochromate In acetonitrile for 0.0333333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation; | 94% |
With thionyl chloride; dihydrogen peroxide In ethanol at 25℃; for 0.0333333h; | 93% |
9-benzhydrylidenefluorene
A
benzophenone
B
9-fluorenone
C
dispiro[9H-fluorene-9,3'-(1,2,4,5-tetroxane)-6',9''-[9H]fluorene]
Conditions | Yield |
---|---|
With oxygen; ozone In dichloromethane at -60℃; Product distribution; ozonolysis; | A 98% B 57% C 20% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; tricyclohexylphosphine In N,N-dimethyl-formamide at 90℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With 1,2-dichlorotetramethylsilane; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine at 145℃; for 15h; | 97% |
9-diazofluorenone
A
9H-fluorene
B
9-fluorenone
C
di-fluoren-9-ylidene-hydrazine
Conditions | Yield |
---|---|
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 20 - 23℃; Pt-cathode; | A 1% B 0.5% C 97% |
Conditions | Yield |
---|---|
With eosin y In water; acetonitrile at 20℃; for 2h; Irradiation; | 97% |
With nitric acid; arsenic(III) trioxide In dichloromethane at 0 - 5℃; | 94% |
Stage #1: 1,2;3,4-dibenzo<4.5>spiro-6,10-dithiodecane With trichloroisocyanuric acid; silica gel at 20℃; for 0.05h; Stage #2: With water at 20℃; | 91% |
9-fluorenone
Conditions | Yield |
---|---|
With air | 97% |
carbon monoxide
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
9-fluorenone
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; palladium diacetate In 1,2-dichloro-ethane at 120℃; under 760.051 Torr; for 8h; Reagent/catalyst; Solvent; Temperature; | 97% |
Conditions | Yield |
---|---|
Stage #1: diethyl (9H-fluoren-9-yl)phosphonate With sodium t-butanolate In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With oxygen In N,N-dimethyl-formamide at 25℃; for 8h; stereoselective reaction; | 97% |
tert.-butylhydroperoxide
9H-fluorene
A
9-fluorenone
B
9-(tert-butylperoxy)-9H-fluorene
Conditions | Yield |
---|---|
With bis-(tributyltin oxide) dioxochromium(VI); water In dichloromethane at 40℃; for 24h; | A 96% B 1% |
With copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry; | A 84% B 5% |
With 2-Picolinic acid; ferric nitrate In pyridine; acetic acid for 0.5h; Product distribution; Mechanism; variation of reaction time; also under air; | A 0.76 mmol B 0.20 mmol |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; bis-(tributyltin oxide) dioxochromium(VI) In dichloromethane at 40℃; for 24h; | A 96% B 1% |
With tert.-butylhydroperoxide; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester In tetrachloromethane; dichloromethane at 0℃; for 8h; Yield given; | A n/a B 21% |
With tert.-butylhydroperoxide; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester In tetrachloromethane; dichloromethane at 0℃; for 8h; Yields of byproduct given; | A n/a B 21% |
2-phenylbenzoic acid ethyl ester
9-fluorenone
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 1h; Friedel-Crafts Acylation; Inert atmosphere; | 96% |
9-hydroxy-9-fluorene carboxylic acid
A
9-fluorenone
B
9-Fluorenol
C
fluorenopinacol
Conditions | Yield |
---|---|
copper(I) oxide In acetonitrile at 50℃; | A 4% B 95% C 1% |
2,2-Diphenylen-1,3-dithian-1-oxid
9-fluorenone
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetonitrile at 20℃; for 12h; | 95% |
fluorene-9-carbaldehyde
9-fluorenone
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether at 25℃; for 0.5h; | 95% |
With tetrafluoroboric acid diethyl ether; iodosylbenzene In dichloromethane at 20℃; for 24h; Inert atmosphere; | 87% |
With Co(nmp)2; oxygen; triethylamine In isopropyl alcohol at 60℃; for 12h; Schlenk technique; Green chemistry; | 83% |
With Nitrosobenzene In dichloromethane at 50℃; for 24h; Sealed tube; | 45% |
Conditions | Yield |
---|---|
With phenylphosphane at 140℃; for 72h; | 100% |
With iodine; hypophosphorous acid In acetic acid for 24h; Reduction; Heating; | 99% |
With formic acid In water at 130℃; for 6h; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 20℃; for 16h; | 100% |
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 20h; | 100% |
With sodium tetrahydroborate In tetrahydrofuran; water for 0.2h; Heating; | 99% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In ethanol at 50 - 60℃; for 1h; | 100% |
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 24h; | 100% |
With hydroxylamine hydrochloride In ethanol at 20℃; Reflux; | 100% |
9-fluorenone
2,7-dibromofluorene-9-one
Conditions | Yield |
---|---|
With bromine In water at 80℃; for 10h; | 100% |
With bromine In water at 80℃; for 12h; pH=7; regioselective reaction; | 98% |
With phosphorus pentaoxide; bromine; sodium thiosulfate In methanol; water; phosphorous acid trimethyl ester | 94% |
Conditions | Yield |
---|---|
for 0.0833333h; Inert atmosphere; Neat (no solvent); | 100% |
With piperidine In ethanol at 20℃; for 0.5h; Knoevenagel condensation; | 87% |
With ethanol; ammonia |
Conditions | Yield |
---|---|
With 8-(N,N-dimethylaminomethyl)-1-naphthyl-(Ph)SiH2 at 25℃; for 12h; | A 100% B n/a |
9-fluorenone
2-(phenylethynyl)phenylacetylene
9-[[2-(phenylethynyl)phenyl]ethynyl]-9H-fluoren-9-ol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 2.5h; | 100% |
Stage #1: 2-(phenylethynyl)phenylacetylene With n-butyllithium In diethyl ether; hexane at 0 - 20℃; Stage #2: 9-fluorenone In diethyl ether; hexane at 20℃; for 2h; |
Conditions | Yield |
---|---|
With potassium hydroxide at 20 - 83℃; for 0.333333h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique; | 100% |
In diethyl ether; dibutyl ether at 0℃; | 75% |
In tetrahydrofuran at 0 - 25℃; for 2.5h; |
Conditions | Yield |
---|---|
With perchloric acid adsorbed on silica gel at 80℃; Inert atmosphere; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With trimethylsilylazide In methanol at 90℃; for 24h; Solvent; Reagent/catalyst; Temperature; Ugi Condensation; Inert atmosphere; | 99.9% |
Conditions | Yield |
---|---|
With potassium bromate; tetrabutyl-ammonium chloride; ammonium bromide In water at 75℃; for 6h; Temperature; | 99.2% |
With bromine In water at 80℃; for 4h; regioselective reaction; | 94% |
With bromine In water at 80 - 85℃; for 4.5h; | 90.4% |
9-fluorenone
fluoren-9-ylidene-hydrazine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 15h; Reflux; | 99% |
With hydrazine hydrate for 4h; Reflux; | 95% |
With hydrazine In water; butan-1-ol for 4h; Reflux; | 93% |
Conditions | Yield |
---|---|
With vanadium monochloride In tetrahydrofuran for 12h; Reflux; Inert atmosphere; | 99% |
With titanium tetrachloride; zinc In tetrahydrofuran for 16h; Heating; | 94% |
With titanium; chloro-trimethyl-silane In 1,2-dimethoxyethane for 4h; Heating; | 94% |
Conditions | Yield |
---|---|
Stage #1: 9-fluorenone With 4-pyridinecarboxylic acid, methyl ester; bis(pinacol)diborane at 20℃; for 1h; Inert atmosphere; Reflux; Stage #2: With potassium hydrogen difluoride at 20℃; for 3h; Inert atmosphere; | 99% |
With zinc(II) chloride; zinc In tetrahydrofuran; water for 0.5h; Ambient temperature; | 94% |
With europium(III) chloride In N,N-dimethyl-formamide electrolysis, Bu4NI; | 94% |
Conditions | Yield |
---|---|
With cobalt(II) bromide In dichloromethane for 3.5h; Ambient temperature; | 99% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere; | 99% |
With silica gel; zirconium(IV) chloride In dichloromethane for 0.5h; Ambient temperature; | 98% |
9-fluorenone
(aminooxy)acetic acid hemihydrochloride
2-(9H-fluoren-9-ylideneaminooxy)acetic acid
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid at 150℃; for 3h; Heating / reflux; | 99% |
With sodium acetate In ethanol |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; Barbier Coupling Reaction; | 99% |
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 9-fluorenone With cerium(III) chloride bis(lithium chloride) In tetrahydrofuran for 0.25h; | 95% |
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 55 - 60℃; for 2.5h; Inert atmosphere; Stage #2: 9-fluorenone In tetrahydrofuran at 55 - 60℃; for 2.5h; Inert atmosphere; | 88% |
9-fluorenone
o-bis(mercaptomethyl)benzene
1,2;3,4;8,9-tribenzo<4.6>spiro-6,11-dithioundecane
Conditions | Yield |
---|---|
With Montmorillonite KSF In benzene for 16h; Heating; | 99% |
9-fluorenone
2,7-diiodofluoren-9-one
Conditions | Yield |
---|---|
With potassium permanganate; sulfuric acid; iodine In acetic acid at 100℃; for 1h; | 99% |
With sulfuric acid; iodine; acetic acid; periodic acid In water Heating; | 98% |
With iodine tris(trifluoroacetate) In dichloromethane for 6h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 16h; | 99% |
With Montmorillonite K 10; toluene-4-sulfonic acid In methanol at 20℃; for 96h; | 93% |
hexafluorophosphoric acid In methanol at 65 - 67℃; for 20h; | 93.61% |
Molecular Structure:
Molecular Formula: C13H8O
Molecular Weight: 180.202
IUPAC Name: Fluoren-9-one
Synonyms of 9H-Fluoren-9-one (CAS NO.486-25-9): 9-Fluorenone ; 9-Oxofluorene ; 9H-Fluoren-9-one ; AI3-00858 ; CCRIS 593 ; Diphenylene ketone ; EINECS 207-630-7 ; Fluoren-9-one ; Fluorenone ; HSDB 5490 ; NSC 5181
CAS NO: 486-25-9
Classification Code: Drug / Therapeutic Agent ; Mutation data ; Tumor data
Melting point: 80-83 °C
Index of Refraction: 1.667
Molar Refractivity: 53.92 cm3
Molar Volume: 144.8 cm3
Surface Tension: 52.3 dyne/cm
Density: 1.244 g/cm3
Flash Point: 144.1 °C
Enthalpy of Vaporization: 58.52 kJ/mol
Boiling Point: 341.5 °C at 760 mmHg
Vapour Pressure: 8.01E-05 mmHg at 25°C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 2gm/kg (2000mg/kg) | Pharmaceutical Chemistry Journal Vol. 23, Pg. 325, 1989. |
9H-Fluoren-9-one (CAS NO.486-25-9) is reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Hazard Codes of 9H-Fluoren-9-one (CAS NO.486-25-9): Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37/39-27-26
S24/25: Avoid contact with skin and eyes.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S27: Take off immediately all contaminated clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: LL8925000
Hazard Note: Irritant
HS Code: 29143900
Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
1. Fire Fighting Measures of 9H-Fluoren-9-one (CAS NO.486-25-9)
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
2. Handling and Storage
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.
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