Product Name

  • Name

    6-Chlorooxindole

  • EINECS 1312995-182-4
  • CAS No. 56341-37-8
  • Article Data30
  • CAS DataBase
  • Density 1.362 g/cm3
  • Solubility
  • Melting Point 195-199 °C(lit.)
  • Formula C8H6ClNO
  • Boiling Point 329 °C at 760 mmHg
  • Molecular Weight 167.595
  • Flash Point 152.8 °C
  • Transport Information
  • Appearance Off-white to tan crystalline powder
  • Safety 37/39-36-26
  • Risk Codes 22-43-36/37/38
  • Molecular Structure Molecular Structure of 56341-37-8 (6-Chlorooxindole)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 6-Chloro-1,3-dihydro-2H-indol-2-one;6-Chloro-1,3-dihydroindol-2-one;6-Chloro-2-indolinone;6-Chloro-2-oxindole;6-Chloro-2-oxoindoline;
  • PSA 29.10000
  • LogP 1.97260

Synthetic route

6-chloroisatin
6341-92-0

6-chloroisatin

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;88%
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 0.5 h / Heating
2: Na / ethanol / Heating
View Scheme
With sodium ethanolate; hydrazine hydrate In ethanol
methyl 2-(4-chloro-2-nitrophenyl)acetate
147124-37-6

methyl 2-(4-chloro-2-nitrophenyl)acetate

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With iron In acetic acid at 100℃; for 1h;87%
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 2280.15 Torr / Sealed tube
2: ethyl acetate / 6 h / Reflux; Molecular sieve
View Scheme
(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester
10565-16-9

(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With hydrogenchloride; tin In ethanol Heating;79%
dimethyl (4-chloro-2-nitrophenyl)malonate
147124-32-1

dimethyl (4-chloro-2-nitrophenyl)malonate

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With iron; acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 25 - 105℃; Large scale;75%
Stage #1: dimethyl (4-chloro-2-nitrophenyl)malonate With hydrogenchloride; water In methanol at 20 - 95℃; Large scale;
Stage #2: With tin In methanol at 45 - 95℃; Large scale;
75%
Stage #1: dimethyl (4-chloro-2-nitrophenyl)malonate With lithium chloride In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: With iron; acetic acid at 100℃; for 1h;
dimethyl 4-chloro-2-nitrophenyl malonate

dimethyl 4-chloro-2-nitrophenyl malonate

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With hydrogen; acetic acid; Pt/C In water71%
4-chloro-2-nitro-phenylacetic acid
37777-71-2

4-chloro-2-nitro-phenylacetic acid

A

6-chloro-1-hydroxy-indolin-2-one
28230-26-4

6-chloro-1-hydroxy-indolin-2-one

B

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitro-phenylacetic acid With 1,10-Phenanthroline; platinum on carbon; hydrogen In ethanol at 20℃; under 7500.75 Torr; Flow reactor; Green chemistry;
Stage #2: With acetic acid In ethanol at 20℃; Green chemistry;
A 63%
B n/a
3-Chloroacetanilide
588-07-8

3-Chloroacetanilide

ethyl iodoacetae
623-48-3

ethyl iodoacetae

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; regioselective reaction;53%
2-chloro-N-(3-chlorophenyl)acetamide
2564-05-8

2-chloro-N-(3-chlorophenyl)acetamide

A

4-chloroindolin-2-one
20870-77-3

4-chloroindolin-2-one

B

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With aluminium trichloride 1. 50-60 deg C, 10 min; 2. 150-160 deg C, 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With aluminium trichloride Product distribution; 50-60 deg C, 10 min; 150-160 deg C, 2 h;
6-chloroisatin 3-hydrazone
879-32-3

6-chloroisatin 3-hydrazone

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With sodium In ethanol Heating; Yield given;
With potassium tert-butylate In ethanol for 2h; Reflux; Inert atmosphere;
2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tBuOK / dimethylformamide / 0.17 h / 90 °C
1.2: dimethylformamide / 2 h / 90 °C
2.1: LiCl / dimethylsulfoxide / 3 h / 100 °C
2.2: acetic acid; iron / 1 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: 84 percent / NaH / dimethylsulfoxide / 100 °C
2: 79 percent / Sn, HCl / ethanol / Heating
View Scheme
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: 69 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C
3: 87 percent / Fe powder / acetic acid / 1 h / 100 °C
View Scheme
3-chloro-aniline
108-42-9

3-chloro-aniline

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / benzene / Heating
2: AlCl3 / 50-60 deg C, 10 min; 150-160 deg C, 2 h
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 4 steps
1: sodium sulfate; sulfuric acid; hydroxylamine hydrochloride / water / 0.5 h / 130 °C
2: sulfuric acid / 1 h / 50 - 70 °C
3: hydrazine hydrate / ethanol / 0.5 h / Inert atmosphere; Reflux
4: potassium tert-butylate / ethanol / 2 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 20 °C / Inert atmosphere
2: palladium diacetate; silver(I) acetate; trifluoroacetic acid / 24 h / 120 °C / Sealed tube; Inert atmosphere; Schlenk technique
View Scheme
4-chloro-2-nitro-phenylacetic acid
37777-71-2

4-chloro-2-nitro-phenylacetic acid

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitro-phenylacetic acid With iron; acetic acid In methanol at 50 - 75℃; for 1h;
Stage #2: With hydrogenchloride In methanol; water at 20 - 25℃;
Multi-step reaction with 2 steps
1: sodium dithionite / ethanol / 4 h / 40 - 45 °C
2: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5
View Scheme
6-chloro-3-iminoindolin-2-one
1261152-95-7

6-chloro-3-iminoindolin-2-one

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid; water
2.1: hydrazine hydrate / ethanol / Reflux
2.2: Reflux
View Scheme
Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide
17122-55-3

Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
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
2-nitro-4-chlorobenzene diazonium tetrafluoroborate

2-nitro-4-chlorobenzene diazonium tetrafluoroborate

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tris(bipyridine)ruthenium(II) dichloride hexahydrate; oxygen / 20 °C / Irradiation
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 2280.15 Torr / Sealed tube
3: ethyl acetate / 6 h / Reflux; Molecular sieve
View Scheme
methyl 2-(2-amino-4-chlorophenyl)acetate

methyl 2-(2-amino-4-chlorophenyl)acetate

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
In ethyl acetate for 6h; Reflux; Molecular sieve;
(2-amino-4-chlorophenyl)acetic acid
177985-31-8

(2-amino-4-chlorophenyl)acetic acid

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 70 - 75℃; for 2h; pH=2 - 2.5;
2-(4-chloro-2-nitrophenyl)malonate potassium

2-(4-chloro-2-nitrophenyl)malonate potassium

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol / 1 h / 0 - 40 °C / pH 6 - 6.5
2: sodium dithionite / ethanol / 4 h / 40 - 45 °C
3: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5
View Scheme
2-(4-chloro-2-nitrophenyl)malonate sodium

2-(4-chloro-2-nitrophenyl)malonate sodium

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol / 1 h / 0 - 40 °C / pH 6 - 6.5
2: sodium dithionite / ethanol / 4 h / 40 - 45 °C
3: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5
View Scheme
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one
215959-30-1

3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In water; tert-butyl alcohol at 20℃; for 3.5h;100%
With pyridinium perbromide hydrobromide In water; tert-butyl alcohol for 16h;99%
With copper(ll) bromide In ethyl acetate at 80℃;
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

Me2NCH(OR)2

Me2NCH(OR)2

6-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one

6-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
In chloroform Heating;100%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

methyl 2-oxobutanoate
3952-66-7

methyl 2-oxobutanoate

C13H14ClNO4

C13H14ClNO4

Conditions
ConditionsYield
With piperidine In methanol at 0 - 20℃; for 24h;97%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

2-fluoro-3-chlorobenzaldehyde
85070-48-0

2-fluoro-3-chlorobenzaldehyde

6-chloro-3-[1-(3-chloro-2-fluorophenyl)-meth-(E)-ylidene]-1,3-dihydroindol-2-one
908027-64-5

6-chloro-3-[1-(3-chloro-2-fluorophenyl)-meth-(E)-ylidene]-1,3-dihydroindol-2-one

Conditions
ConditionsYield
With piperidine In methanol at 20℃; Reflux;96%
With piperidine for 6h; Reflux;95%
With piperidine for 6h; Reflux;95%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

salicylaldehyde
90-02-8

salicylaldehyde

C15H8ClNO

C15H8ClNO

Conditions
ConditionsYield
With H4[PVMo11O40] suppoted montmorillonite K-10 clay In neat (no solvent) at 100℃; for 1h; Green chemistry;96%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

5-bromo-6-chloro-1,3-dihydro-2H-indol-2-one

5-bromo-6-chloro-1,3-dihydro-2H-indol-2-one

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 3h;95.8%
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 3h;95.8%
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 5h;4.5 g
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

E/Z-6-chloro-3-[1-(3-chlorophenyl)methylidene]-1,3-dihydroindol-2-one
387344-30-1

E/Z-6-chloro-3-[1-(3-chlorophenyl)methylidene]-1,3-dihydroindol-2-one

Conditions
ConditionsYield
With pyrrolidine In methanol at 70℃; for 3h;95%
With pyrrolidine In methanol at 70℃; for 3h;95%
With pyrrolidine In methanol at 70℃; for 3h;95%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

acetone
67-64-1

acetone

6-chloro-3-(propan-2-ylidene)indolin-2-one
1374606-24-2

6-chloro-3-(propan-2-ylidene)indolin-2-one

Conditions
ConditionsYield
With morpholine for 16h; Knoevenagel Condensation; Reflux;95%
With piperidine In ethanol at 23℃; for 4h;
With piperidine at 120℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
With piperidine In ethanol at 23℃; for 4h; Inert atmosphere;
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

diphenyl(vinyl)sulfonium trifluoromethanesulfonate

diphenyl(vinyl)sulfonium trifluoromethanesulfonate

6'-chloro-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

6'-chloro-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 21℃; for 4h;95%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

2-fluoro-3-chlorobenzaldehyde
85070-48-0

2-fluoro-3-chlorobenzaldehyde

(3E/Z)-6-chloro-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one
897365-76-3

(3E/Z)-6-chloro-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one

Conditions
ConditionsYield
With piperidine In ethanol at 80℃; for 2h; Inert atmosphere;94%
With piperidine In methanol at 50℃; for 3h;89%
With piperidine In ethanol for 8h; Inert atmosphere; Reflux;
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

acetic anhydride
108-24-7

acetic anhydride

1,3-diacetyl-6-chloro-1H-indol-2-yl acetate
1195737-73-5

1,3-diacetyl-6-chloro-1H-indol-2-yl acetate

Conditions
ConditionsYield
With dmap at 150℃; for 1h;93%
With dmap at 150℃; for 1h;93%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

phenyl chloroformate
1885-14-9

phenyl chloroformate

6-chloro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester
301700-14-1

6-chloro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Acylation;92%
With triethylamine In tetrahydrofuran
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

6-chloroindoline-2-thione
392332-34-2

6-chloroindoline-2-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h;92%
Stage #1: 6-chloro-2-oxindole With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃;
Stage #1: 6-chloro-2-oxindole With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃;
With Lawessons reagent In tetrahydrofuran for 24h; Reflux;
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

6-chloro-5-(3-chloro-propionyl)-1,3-dihydro-indol-2-one
860024-14-2

6-chloro-5-(3-chloro-propionyl)-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With aluminum (III) chloride In carbon disulfide at 20℃; for 3h; Heating / reflux;92%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

6-chloro-2-oxindole-3-thione S-oxide
1261171-12-3

6-chloro-2-oxindole-3-thione S-oxide

Conditions
ConditionsYield
With thionyl chloride In acetonitrile at 25 - 30℃; for 0.166667h;92%
3-bromo-2-fluorobenzaldehyde
149947-15-9

3-bromo-2-fluorobenzaldehyde

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

(E/Z)-3-(3-bromo-2-fluoro-benzylidene)-6-chloro-1,3-dihydro-indol-2-one
1309685-47-9

(E/Z)-3-(3-bromo-2-fluoro-benzylidene)-6-chloro-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With piperidine In methanol at 80℃; for 2h;92%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

3-chloro-5-fluorobenzaldehyde
90390-49-1

3-chloro-5-fluorobenzaldehyde

(3E/Z)-6-chloro-3-(3-chloro-5-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one
1309685-27-5

(3E/Z)-6-chloro-3-(3-chloro-5-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one

Conditions
ConditionsYield
With piperidine In methanol at 80℃; for 2h;92%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

chloroacetyl chloride
79-04-9

chloroacetyl chloride

6-chloro-5-(2-chloroacetyl) indolin-2-one
118307-04-3

6-chloro-5-(2-chloroacetyl) indolin-2-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 30℃; for 24h; Inert atmosphere;90.6%
With aluminium trichloride In carbon disulfide
With aluminum (III) chloride In dichloromethane at 0 - 45℃; for 14h; Heating / reflux;
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester
1160653-87-1

4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester
1162669-96-6

E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With piperidine In methanol at 100℃; for 3h;90%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

6-chloro-3-((4-chlorophenyl)thio)indolin-2-one

6-chloro-3-((4-chlorophenyl)thio)indolin-2-one

Conditions
ConditionsYield
With iron(III) chloride; potassium carbonate In dimethyl sulfoxide at 50℃; for 1.5h; Green chemistry;90%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

malononitrile
109-77-3

malononitrile

2-(6-chloro-2-oxoindolin-3-ylidene)malononitrile
1356828-86-8

2-(6-chloro-2-oxoindolin-3-ylidene)malononitrile

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; oxygen In N,N-dimethyl-formamide at 50℃; for 5h; Green chemistry;90%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

6-chloroisatin
6341-92-0

6-chloroisatin

Conditions
ConditionsYield
With oxygen; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 0.5h;89%
Stage #1: 6-chloro-2-oxindole With pyridinium perbromide hydrobromide
Stage #2: With methanol; water
85%
Multi-step reaction with 2 steps
1: CuBr2 / ethyl acetate / 80 °C
2: water / methanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / pyridine*HBr*Br2 / 2-methyl-propan-2-ol; H2O / 16 h
2: 57 percent / H2O / methanol / 50 h / Heating
View Scheme
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

azulene
275-51-4

azulene

1-(6-chloroindol-2-yl)azulene
1365097-46-6

1-(6-chloroindol-2-yl)azulene

Conditions
ConditionsYield
Stage #1: 6-chloro-2-oxindole; azulene With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 2.5h; Vilsmeier-Haack type arylation;
Stage #2: With potassium carbonate In dichloromethane; water
89%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(E)-3-(4-methylbenzylidene)-6-chloroindolin-2-one
1612883-15-4

(E)-3-(4-methylbenzylidene)-6-chloroindolin-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 3h; Reflux;89%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

(3-oxo-butyl)-propyl-carbamic acid tert-butyl ester

(3-oxo-butyl)-propyl-carbamic acid tert-butyl ester

4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester

4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With pyrrolidine In isopropyl alcohol at 90℃; for 48h;88%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

(E)-3-(4-(methylthio)benzylidene)-6-chloroindolin-2-one
1612883-12-1

(E)-3-(4-(methylthio)benzylidene)-6-chloroindolin-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 3h; Reflux;88%
piperidine
110-89-4

piperidine

1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

6-chloro-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

6-chloro-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
In ethanol87%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

acetic anhydride
108-24-7

acetic anhydride

1-acetyl-6-chloroindolin-2-one
651747-72-7

1-acetyl-6-chloroindolin-2-one

Conditions
ConditionsYield
at 130℃; for 7h;87%
With sodium carbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

6-Chlorooxindole Specification

The CAS register number of 6-Chloroindol-2(3H)-one is 56341-37-8. It also can be called as 2H-Indol-2-one,6-chloro-1,3-dihydro- and the systematic name about this chemical is 6-chloro-1,3-dihydro-2H-indol-2-one. The molecular formula about this chemical is C8H6ClNO and the molecular weight is 167.59. It belongs to the following product categories, such as Blocks; IndolesOxindoles; Indole/indoline/oxindole; Indole and Indoline; Starting Raw Materials & Intermediates; Heterocycles; Indoles and derivatives; Indole; Indoles and so on. This chemical is an important pharmaceutical intermediate to product Ziprasidone. If you want to store this chemical, please keep it in a tighely closed container, store it in a dry, cool place and ensure workplace has good ventilation.

Physical properties about 6-Chloroindol-2(3H)-one are: (1)ACD/LogP: 2.17; (2)ACD/LogD (pH 5.5): 2.17; (3)ACD/LogD (pH 7.4): 2.17; (4)ACD/BCF (pH 5.5): 26.03; (5)ACD/BCF (pH 7.4): 26.03; (6)ACD/KOC (pH 5.5): 358.75; (7)ACD/KOC (pH 7.4): 358.75; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 20.31Å2; (11)Index of Refraction: 1.601; (12)Molar Refractivity: 42.18 cm3; (13)Molar Volume: 123 cm3; (14)Polarizability: 16.72x10-24cm3; (15)Surface Tension: 47.5 dyne/cm; (16)Enthalpy of Vaporization: 57.14 kJ/mol; (17)Boiling Point: 329 °C at 760 mmHg; (18)Vapour Pressure: 0.000183 mmHg at 25°C.

Preparation: this chemical can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester. This reaction will need reagent Sn, HCl and solvent ethanol at heating. The yield is about 79%.

Uses of 6-Chloroindol-2(3H)-one: it can be used to produce 3,3-dibromo-6-chloro-1,3-dihydro-indol-2-one. This reaction will need reagent pyridine*HBr*Br2 and solvent 2-methyl-propan-2-ol, H2O with reaction time of 16 hours. The yield is about 99%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and it is irritating to eyes, respiratory system and skin, it may cause sensitization by skin contact. 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: Clc1ccc2c(c1)NC(=O)C2
(2)InChI: InChI=1/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)
(3)InChIKey: CENVPIZOTHULGJ-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)
(5)Std. InChIKey: CENVPIZOTHULGJ-UHFFFAOYSA-N

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