5-fluoro-1H-indole-2,3-dione
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 140℃; for 6h; Temperature; Wolff-Kishner-Huang Minlon Reduction; | 99.1% |
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 0.1h; Inert atmosphere; | 87% |
Stage #1: 5-fluoro-1H-indole-2,3-dione With potassium hydroxide; hydrazine In ethylene glycol at 80℃; for 3h; Stage #2: With hydrogenchloride; water In ethylene glycol at 0 - 20℃; for 12h; pH=1 - 2; | 81.9% |
5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Reflux; | 92.1% |
Stage #1: 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester With hydrogenchloride In methanol; water at 80℃; for 5h; Stage #2: With potassium hydroxide In methanol; water at 40℃; for 0.5h; |
Conditions | Yield |
---|---|
With montmorillonite KSF at 20℃; for 1.08333h; Stolle synthesis; Sonication; Neat (no solvent); | 88% |
methyl 2-(5-fluoro-2-nitrophenyl)acetate
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With iron In acetic acid at 100℃; for 1h; | 87% |
1,3-dihydro-1-hydroxyindole-2-one
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With diethylamino-sulfur trifluoride In dichloromethane at 0℃; for 0.0833333h; | 81% |
5-fluoro-3-hydrazonoindolin-2-one
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 5h; Reflux; | 80.4% |
With potassium tert-butylate In ethanol for 2h; Reflux; Inert atmosphere; | |
With sodium ethanolate |
Conditions | Yield |
---|---|
With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; | 78% |
(5-Fluoro-2-nitro-phenyl)-acetic Acid
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With ammonium formate on silica gel; zinc In carbon dioxide at 50℃; under 90009 Torr; Autoclave; liquid CO2; | 76% |
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 6h; Reflux; | 73.6% |
(2-amino-5-fluoro-phenyl)-acetic acid hydrazide
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
In water | 73% |
In water | 73% |
With hydrogenchloride In water at 20℃; for 12h; pH=3; | 73% |
Conditions | Yield |
---|---|
In water | A 73% B n/a |
In water | A 73% B n/a |
molybdenum hexacarbonyl
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With tetraethylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20 - 110℃; for 1h; | 55% |
2-chloro-N-(4-fluorophenyl)acetamide
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With aluminium trichloride at 220 - 225℃; for 0.5h; | 54% |
With aluminum (III) chloride at 220℃; for 1h; |
3,3-dibromo-5-fluoro-2-oxindole
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With acetic acid; zinc Ambient temperature; |
(2-tert-Butoxycarbonylamino-5-fluoro-phenyl)-acetic acid
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 0.25h; Heating; Yield given; |
4-fluoroaniline
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / AlCl3 / 0.5 h / 220 - 225 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 60 - 70 °C 2.1: sulfuric acid / 80 - 90 °C 3.1: sulfuric acid; water 4.1: hydrazine hydrate / ethanol / Reflux 4.2: Reflux View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 20 °C 2: aluminum (III) chloride / 1 h / 220 °C View Scheme |
2,4-Difluoronitrobenzene
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) NaH / 1) DMSO, 100 deg C, 40 min, 2a) RT, 30 min, 2b) 100 deg C, 1 h 2: 56 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C 3: 87 percent / Fe powder / acetic acid / 1 h / 100 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium methylate / N,N-dimethyl acetamide / 10 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; water / 20 °C 3: hydrogenchloride / water; methanol / 2 h / Inert atmosphere; Reflux View Scheme |
dimethyl 2-(5-fluoro-2-nitrophenyl)malonate
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 56 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C 2: 87 percent / Fe powder / acetic acid / 1 h / 100 °C View Scheme |
4-fluor-2-methylaniline
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / Heating 2: 1) s-BuLi / 1) THF, cyclohexane, -40 to -20 deg C, 2) -40 deg C, 1 min 3: 10percent HCl / ethanol / 0.25 h / Heating View Scheme |
tert-butyl (4-fluoro-2-methylphenyl)carbamate
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) s-BuLi / 1) THF, cyclohexane, -40 to -20 deg C, 2) -40 deg C, 1 min 2: 10percent HCl / ethanol / 0.25 h / Heating View Scheme |
5-fluoro-1H-indole
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 48 percent / pyridinium bromide perbromide / 2-methyl-propan-2-ol / 20 h / 25 °C 2: Zn, AcOH / Ambient temperature View Scheme |
(5-Fluoro-2-nitro-phenyl)-acetic Acid
5-fluoroindol-2(3H)-one
tert-butylhypochlorite
methylthioacetic acid ethyl ester
4-fluoroaniline
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride; triethylamine In diethyl ether; ethanol; dichloromethane; water |
tert-butylhypochlorite
methylthioacetic acid ethyl ester
4-fluoroaniline
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride; triethylamine In diethyl ether; ethanol; dichloromethane; water |
C8H5FN2O
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid; water 2.1: hydrazine hydrate / ethanol / Reflux 2.2: Reflux View Scheme |
N-(4-fluorophenyl)-2-(hydroxyimino) acetamide
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / 80 - 90 °C 2.1: sulfuric acid; water 3.1: hydrazine hydrate / ethanol / Reflux 3.2: Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid / 1 h / 50 - 70 °C 2: hydrazine hydrate / ethanol / 0.5 h / Inert atmosphere; Reflux 3: potassium tert-butylate / ethanol / 2 h / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / 0.17 h / Inert atmosphere 2: titanium tetrachloride; zinc / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / water / 50 - 75 °C 2: hydrazine hydrate / water / 6 h / 140 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / 2 h / 60 - 90 °C 2: hydrazine hydrate / water; ethanol / 10 h / 100 °C View Scheme |
5-fluoroindol-2(3H)-one
3-bromoazulene-1-carbaldehyde
(3E)-3-(((4Z,6Z,8E)-1-bromoazulen-3-yl)methylene)-5-fluoroindolin-2-one
Conditions | Yield |
---|---|
With piperidine In ethanol for 2h; Heating / reflux; | 100% |
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
5-fluoroindol-2(3H)-one
5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
Conditions | Yield |
---|---|
With pyrrolidine In ethanol for 3h; Reflux; | 98% |
With pyrrolidine In ethanol for 3h; Reflux; | 98.2% |
With piperidine In ethanol Inert atmosphere; | 90% |
5-fluoroindol-2(3H)-one
formic acid ethyl ester
Conditions | Yield |
---|---|
With sodium methylate In methanol Reflux; | 98% |
5-fluoroindol-2(3H)-one
1,5-diphenyl-1,4-pentadiene-3-one
5'-fluoro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione
Conditions | Yield |
---|---|
With Boc-D-Phg-OH; 9-amino-9-deoxy-epiquinine In toluene at 40℃; for 72h; Air; optical yield given as %ee; enantioselective reaction; | 98% |
5-fluoroindol-2(3H)-one
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
sunitinib
Conditions | Yield |
---|---|
With piperidine In toluene for 3h; Solvent; Reagent/catalyst; Knoevenagel Condensation; Reflux; | 97.3% |
With piperidine In toluene for 3h; Reagent/catalyst; Solvent; Reflux; | 97.3% |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3.5h; Aldol Condensation; Darkness; Inert atmosphere; | 94% |
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
5-fluoroindol-2(3H)-one
5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 5-fluoroindol-2(3H)-one With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 5h; Reflux; Stage #2: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With trimethylsilyl trifluoromethanesulfonate | 97% |
pyrrolidine In ethanol for 3h; Heating / reflux; | 96% |
With pyrrolidine In ethanol for 3h; Heating / reflux; | 96% |
3,5-dimethyl-4-nitro-1H-pyrrole-2-carbaldehyde
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With pyrrolidine In ethanol Reflux; | 96% |
With pyrrolidine In ethanol Reflux; | 96% |
With pyrrolidine In ethanol Reflux; | 96% |
With piperidine In ethanol Knoevenagel condensation; Heating; | 87% |
With pyrrolidine In ethanol Reflux; |
5-fluoroindol-2(3H)-one
3-iodo-1H-indazole-6-carbaldehyde
Conditions | Yield |
---|---|
With piperidine In methanol at 60℃; for 3h; | 96% |
5-fluoroindol-2(3H)-one
5-[13C]formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
Conditions | Yield |
---|---|
With pyrrolidine In ethanol for 3h; Reflux; | 95% |
5-fluoroindol-2(3H)-one
malononitrile
2-(5-fluoro-2-oxoindolin-3-ylidene)malononitrile
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate; oxygen In N,N-dimethyl-formamide at 50℃; for 4h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With piperidine In methanol at 0 - 20℃; for 24h; | 93% |
6-fluoro-1H-indole-3-carbaldehyde
5-fluoroindol-2(3H)-one
(Z)-5-fluoro-3-((5-fluoro-1H-indol-3-yl)methylene)indolin-2-one
Conditions | Yield |
---|---|
With piperidine In methanol for 5h; Reflux; | 92% |
Conditions | Yield |
---|---|
With C31H43Cl2N4Pd; potassium tert-butylate In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique; | 92% |
5-fluoroindol-2(3H)-one
2-bromo-4-methoxybenzaldehyde
Conditions | Yield |
---|---|
With piperidine In ethanol for 1.5h; Reflux; | 92% |
5-fluoroindol-2(3H)-one
5-fluoro-1H-indole
Conditions | Yield |
---|---|
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 120℃; for 36h; Inert atmosphere; | 92% |
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 120℃; for 36h; Schlenk technique; Sealed tube; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
Stage #1: C18H22N4O4 With triethylamine In chloroform at 0℃; for 0.166667h; Stage #2: 5-fluoroindol-2(3H)-one In chloroform at 65℃; for 8h; Solvent; Temperature; | 92% |
5-fluoroindol-2(3H)-one
acetic anhydride
1,3-diacetyl-5-fluoro-1H-indol-2-yl acetate
Conditions | Yield |
---|---|
With dmap at 150℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20 - 65℃; for 2h; Molecular sieve; Inert atmosphere; optical yield given as %de; diastereoselective reaction; | A 5% B 91% |
Conditions | Yield |
---|---|
With C31H43Cl2N4Pd; potassium tert-butylate In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique; | 91% |
2-methylquinoline
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With iron(II) acetate In N,N-dimethyl-formamide at 80℃; for 5h; Green chemistry; | 91% |
5-fluoroindol-2(3H)-one
5-fluoroindoline-2-thione
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h; | 90% |
With phosphorous (V) sulfide; sodium hydrogencarbonate In tetrahydrofuran for 3h; Ambient temperature; | 84% |
Stage #1: 5-fluoroindol-2(3H)-one With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran at 120℃; for 1h; | 75% |
Stage #1: 5-fluoroindol-2(3H)-one With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; | |
Stage #1: 5-fluoroindol-2(3H)-one With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; |
5-fluoroindol-2(3H)-one
(R)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde
(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-ylpropyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one
Conditions | Yield |
---|---|
With piperidine In ethanol at 20 - 80℃; Darkness; | 90% |
With piperidine In ethanol at 20 - 80℃; for 2h; Darkness; | 90% |
With piperidine In ethanol at 20℃; |
1-methyl-2-formyl-1H-benzimidazole
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With piperidine In ethanol Knoevenagel Condensation; Reflux; stereoselective reaction; | 90% |
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
Stage #1: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 35℃; for 3h; Stage #2: 5-fluoroindol-2(3H)-one; C14H21NO5 With triethylamine In tetrahydrofuran; acetonitrile at 60℃; for 24h; | 90% |
5-fluoroindol-2(3H)-one
3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde
Conditions | Yield |
---|---|
With piperidine In ethanol for 12h; Reflux; | 90% |
5-fluoroindol-2(3H)-one
Conditions | Yield |
---|---|
With piperidine In ethanol at 60℃; | 90% |
5-fluoroindol-2(3H)-one
ethyl 3-(2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoate
(Z)-ethyl 3-{2-[(5-fluoro-2-oxoindolin-3-ylidene)methyl]-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate
Conditions | Yield |
---|---|
With piperidine In ethanol for 12h; Aldol condensation; Reflux; | 89% |
IUPAC Name: 5-Fluoro-1,3-dihydroindol-2-one
Molecular Formula: C8H6FNO
Molecular Weight: 151.14 g/mol
Canonical SMILES: C1C2=C(C=CC(=C2)F)NC1=O
InChI: InChI=1S/C8H6FNO/c9-6-1-2-7-5(3-6)4-8(11)10-7/h1-3H,4H2,(H,10,11)
Product Categories: INDOLE; blocks; FluoroCompounds; IndolesOxindoles; Indole/indoline/oxindole; Indole and Indoline; Heterocycles; Indoles and derivatives; Halides; Pyrroles & Indoles; ketone; Sunitinib; Aromatics Compounds; Intermediate of sunitinib malate; Aromatics; Pyrroles & Indoles; Boronic Acid;Heterocyclic Compounds; Building Blocks; Heterocyclic Building Blocks; Indoles; Fluorinated heterocyclic series
Index of Refraction: 1.56
Molar Refractivity: 37.28 cm3
Molar Volume: 115.2 cm3
Polarizability: 14.78×10-24 cm3
Surface Tension: 41.8 dyne/cm
Density: 1.311 g/cm3
Flash Point: 139.6 °C
Enthalpy of Vaporization: 54.78 kJ/mol
Boiling Point: 307.2 °C at 760 mmHg
Melting Point: 143-147 °C(lit.)
Storage temperature: Keep Cold
Vapour Pressure of 5-Fluorooxindole (CAS NO.56341-41-4): 0.000736 mmHg at 25 °C
Safty informations of 5-Fluorooxindole (CAS NO.56341-41-4):
Hazard Codes:XiC
Risk Statements: 36/37/38-34
R36/37/38:Irritating to eyes, respiratory system and skin.
R34:Causes burns.
Safety Statements: 22-24/25-45-36/37/39-27-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
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
Hazard Note: Irritant/Keep Cold
HazardClass: IRRITANT, KEEP COLD
5-Fluorooxindole (CAS NO.56341-41-4), its Synonyms are 5-Fluoroindole-2-One ; 5-Fluoro-1,3-dihydro-indol-2-one ; 5-Fluorooxindole 98% . It is light yellow crystalline.
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