Conditions | Yield |
---|---|
With sulfuric acid In water at 80℃; for 0.333333h; | 88.6% |
With sulfuric acid In water at 50 - 75℃; Temperature; | 88.2% |
With sulfuric acid at 20℃; | 85% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid at 50 - 75℃; for 0.333333h; | 88.2% |
Conditions | Yield |
---|---|
With iodine pentoxide In dimethyl sulfoxide at 80℃; | 87% |
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry; | 72% |
3-(4-fluorophenylimino)-5-fluoro-N-(4-fluorophenyl)-3H-indole-2-amine
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water for 0.333333h; Reflux; | 85% |
5-fluoroindol-2(3H)-one
A
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With oxygen; sodium iodide In tetrahydrofuran at 60℃; for 12h; Schlenk technique; chemoselective reaction; | A 80% B 8% |
carbon monoxide
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
Stage #1: N'-(2-bromo-4-fluorophenyl)-N,N-dimethylurea With methyllithium In tetrahydrofuran; diethyl ether at 0℃; Stage #2: With tert.-butyl lithium In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 1h; Stage #3: carbon monoxide In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 0.5h; | 79% |
Yield given; Multistep reaction; |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 16h; | 78.7% |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 18h; | 68% |
Conditions | Yield |
---|---|
Stage #1: chloral hydrate; 4-fluoroaniline With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water Stage #2: With sulfuric acid at 60 - 80℃; | 63% |
Stage #1: chloral hydrate; 4-fluoroaniline With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate for 0.166667h; Heating; Stage #2: With sulfuric acid for 1h; Heating; | |
Stage #1: chloral hydrate; 4-fluoroaniline With hydroxylamine hydrochloride; sodium sulfate In water Sandmeyer reaction; Stage #2: With sulfuric acid In methanol Sandmeyer reaction; |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid 1) 50 deg C, 30 min; 2) 80 deg C, 10 min; | 62% |
Conditions | Yield |
---|---|
Stage #1: chloral ethyl hemiacetal; 4-fluoroaniline With hydrogenchloride; sodium sulfate In water for 1h; Stage #2: With hydroxylamine hydrochloride In water at 10 - 80℃; for 1.5h; Stage #3: With sulfuric acid at 60℃; for 6h; | 61% |
(E)-N-(4-fluorophenyl)-2-(hydroxyimino)acetamide
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid In water at 50 - 90℃; | 52% |
With sulfuric acid In water at 50 - 90℃; | 52% |
5-fluoroindol-2(3H)-one
A
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With oxygen; sodium iodide In dimethyl sulfoxide at 100℃; for 12h; Schlenk technique; chemoselective reaction; | A 29% B 52% |
Conditions | Yield |
---|---|
With H-β zeolite In 1,2-dichloro-ethane at 80℃; for 36h; Inert atmosphere; | 51% |
3,3-dibromo-5-fluoro-2-oxindole
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With water In methanol for 2h; Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydroxylamine sulfate; sodium sulfate; HCl / ethanol; H2O 2: H2SO4 View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / NH2OH*HCl; sodium sulfate / H2O / 0.05 h / microwave irradiation 2: 61 percent / H2SO4 (86 percent) / 0.01 h / microwave irradiation View Scheme | |
Multi-step reaction with 2 steps 1: NH2OH 2: conc. H2SO4 / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Et3N / tetrahydrofuran / 2 h / 0 °C 1.2: 71 percent / tetrahydrofuran / 1 h / 0 °C 2.1: MeLi / tetrahydrofuran; diethyl ether / 0 °C 2.2: t-BuLi / tetrahydrofuran; diethyl ether; heptane / 1 h / 0 °C 2.3: 79 percent / tetrahydrofuran; diethyl ether; heptane / 0.5 h / 0 °C View Scheme |
5-fluoroindol-2(3H)-one
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CuBr2 / ethyl acetate / 80 °C 2: water / methanol / 2 h / Heating View Scheme | |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 24h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH2OH*HCl, Na2SO4 2: H2SO4 View Scheme |
5-iodoisatin
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
Stage #1: 5-iodoisatin With tetrakis(triphenylphosphine) palladium(0); bis(tri-n-butyltin); lithium chloride In 1,4-dioxane at 23 - 100℃; Inert atmosphere; Stage #2: With silver trifluoromethanesulfonate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) In acetone at 23℃; for 0.333333h; Inert atmosphere; regiospecific reaction; | 11.9 mg |
C8H5FN2O
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid; water |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; sulfuric acid; sodium sulfate; hydroxylamine hydrochloride / water / 100 °C 2: sulfuric acid / 85 °C View Scheme |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation; | 100% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
5-fluoro-1H-indole-2,3-dione
5-fluoro-1-n-propylisatin
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
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-1H-indole-2,3-dione
3,3'-methylenedianiline
Conditions | Yield |
---|---|
In water at 20℃; for 22h; | 99% |
With acetic acid In ethanol for 5h; Heating; | 68% |
In ethanol Heating; |
indole
5-fluoro-1H-indole-2,3-dione
5'-fluoro-1H,1''H-[3,3':3',3''-terindol]-2'(1'H)-one
Conditions | Yield |
---|---|
With titanium(IV) oxide In water at 20℃; Green chemistry; | 99% |
With bromine In acetonitrile at 20℃; for 7h; | 92% |
With C14H32N2O6S2(2+)*2ClO4(1-) In neat (no solvent) at 110℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; | 89% |
5-fluoro-1H-indole-2,3-dione
3-(trifluoromethyl)propiophenone
6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 5-fluoro-1H-indole-2,3-dione; 3-(trifluoromethyl)propiophenone With potassium hydroxide In ethanol; water for 1h; Reflux; Stage #2: With hydrogenchloride In water pH=~ 3; Product distribution / selectivity; | 99% |
Stage #1: 5-fluoro-1H-indole-2,3-dione With potassium hydroxide In ethanol; water for 0.25h; Stage #2: 3-(trifluoromethyl)propiophenone In ethanol; water for 1h; Reflux; Stage #3: With hydrogenchloride In water pH=6; | 34% |
5-fluoro-1H-indole-2,3-dione
aminomalonic acid diethyl ester
dimethyl acetylenedicarboxylate
5',5'-diethyl 3',4'-dimethyl 5-fluoro-2-oxospiro[indoline-3,2'-pyrrole]-3',4',5',5'(1'H)-tetracarboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; for 36h; Time; Molecular sieve; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
5-fluoro-1H-indole-2,3-dione
5-propyl-2,4-dihydro-3H-pyrazol-3-one
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea In acetonitrile at 25℃; for 12h; enantioselective reaction; | 99% |
1-(pyridin-2-yl)-butan-2-one
5-fluoro-1H-indole-2,3-dione
2-ethyl-6-fluoro-3-(pyridin-2-yl)quinoline-4-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 90℃; | 99% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With methanol; triethylamine at 20℃; for 24h; | 99% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 20℃; for 12.5h; Reflux; | 98.3% |
5-fluoro-1H-indole-2,3-dione
2-oxo-propionic acid
6-fluoroquinoline-2,4-dicarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 110℃; for 6h; | 98.15% |
With sodium hydroxide at 110℃; for 4h; | 70% |
With potassium hydroxide In water at 40℃; for 16h; Pfitzinger Quinoline Synthesis; | 65% |
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane at 20℃; | 98% |
With piperdinium acetate In water at 100℃; Knoevenagel Condensation; | 90% |
Conditions | Yield |
---|---|
for 0.0333333h; microwave irradiation; | 98% |
5-fluoro-1H-indole-2,3-dione
4R-4-hydroxyproline
5-fluoro-3-(1H-pyrrol-1-yl)-1,3-dihydroindol-2-one
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide In water at 80℃; for 0.5h; Green chemistry; | 98% |
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 110℃; for 0.166667h; Microwave irradiation; | 96% |
With scandium tris(dodecyl sulfate) In water at 80℃; for 0.5h; Green chemistry; | 96% |
With β‐cyclodextrin In water at 60℃; for 1.5h; | 94% |
With iodine In water; acetonitrile at 20℃; for 4h; Irradiation; |
5-fluoro-1H-indole-2,3-dione
dimedone
malononitrile
2-amino-5'-fluoro-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile
Conditions | Yield |
---|---|
With silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride In ethanol at 20℃; for 3.5h; | 98% |
With 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) hydroxide In water at 80℃; for 0.166667h; Green chemistry; | 96% |
In water at 80℃; for 0.133333h; Microwave irradiation; Green chemistry; | 95% |
1H-indene-1,3(2H)-dione
5-fluoro-1H-indole-2,3-dione
N,N-dimethyl-aniline
2-(3-(4-(dimethylamino)phenyl)-5-fluoro-2-oxoindolin-3-yl)-1H-indene-1,3(2H)-dione
Conditions | Yield |
---|---|
With lithium perchlorate In ethanol for 4h; Friedel-Crafts type reaction; Reflux; | 98% |
4-hydroxy[1]benzopyran-2-one
5-fluoro-1H-indole-2,3-dione
malononitrile
2'-amino-5-fluoro-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[2,3-b]chromene]-3'-carbonitrile
Conditions | Yield |
---|---|
With silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride In ethanol at 20℃; for 4.5h; | 98% |
With tetrabutylammonium acetate In melt at 100℃; | 93% |
5-fluoro-1H-indole-2,3-dione
3-acetylcoumarin
(R)-5-fluoro-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
Conditions | Yield |
---|---|
Stage #1: 3-acetylcoumarin With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)(3-vinylquinuclidin-7-yl)methyl)urea In tetrahydrofuran at 5℃; for 0.333333h; Aldol Addition; Stage #2: 5-fluoro-1H-indole-2,3-dione In tetrahydrofuran at 5℃; for 24h; Aldol Addition; enantioselective reaction; | 98% |
5-fluoro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
In chloroform at 61℃; for 15h; Inert atmosphere; | 98% |
The 5-Fluoroindoline-2,3-dione is an organic compound with the formula C8H4FNO2. The IUPAC name of this chemical is 5-fluoro-1H-indole-2,3-dione. With the CAS registry number 443-69-6, it is also named as 1H-Indole-2,3-dione, 5-fluoro-. The product's categories are Isatin Series; Blocks; Indoles Oxindoles; Indole/indoline/oxindole; Indole and Indoline; Indane/Indanone and Derivatives; Sunitinib; Heterocyclic Compounds; Indoles; Simple Indoles; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Boronic Acid; Building Blocks; Heterocyclic Building Blocks; Fluorinated Heterocyclic Series. Besides, it is a red crystalline powder, which is the intermediates of cardiovascular and anti-inflammatory drugs.
Physical properties about 5-Fluoroindoline-2,3-dione are: (1)ACD/LogP: 0.61 ; (2)ACD/LogD (pH 5.5): 0.61; (3)ACD/LogD (pH 7.4): 0.58; (4)ACD/BCF (pH 5.5): 1.71; (5)ACD/BCF (pH 7.4): 1.59; (6)ACD/KOC (pH 5.5): 51.14; (7)ACD/KOC (pH 7.4): 47.53; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)Polar Surface Area: 37.38 Å2; (11)Index of Refraction: 1.584; (12)Molar Refractivity: 37.41 cm3; (13)Molar Volume: 111.7 cm3; (14)Polarizability: 14.83×10-24cm3; (15)Surface Tension: 50.8 dyne/cm; (16)Density: 1.477 g/cm3.
Preparation: this chemical can be prepared by hydroxyimino-acetic acid-(4-fluoro-anilide). This reaction will need reagent sulfuric acid.
Uses of 5-Fluoroindoline-2,3-dione: it can be used to produce 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione. It will need reagent CrO3 and acetic acid.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Fc1cc2c(cc1)NC(=O)C2=O
(2)InChI: InChI=1/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
(3)InChIKey: GKODDAXOSGGARJ-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
(5)Std. InChIKey: GKODDAXOSGGARJ-UHFFFAOYSA-N
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