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56341-37-8

Basic Information
CAS No.: 56341-37-8
Name: 6-Chlorooxindole
Article Data: 30
Molecular Structure:
Molecular Structure of 56341-37-8 (6-Chlorooxindole)
Formula: C8H6ClNO
Molecular Weight: 167.595
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;
EINECS: 1312995-182-4
Density: 1.362 g/cm3
Melting Point: 195-199 °C(lit.)
Boiling Point: 329 °C at 760 mmHg
Flash Point: 152.8 °C
Appearance: Off-white to tan crystalline powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-43-36/37/38
Safety: 37/39-36-26
PSA: 29.10000
LogP: 1.97260
Synthetic route
6341-92-0

6-chloroisatin

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
147124-37-6

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

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
10565-16-9

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

56341-37-8

6-chloro-2-oxindole

Conditions
ConditionsYield
With hydrogenchloride; tin In ethanol Heating;79%
147124-32-1

dimethyl (4-chloro-2-nitrophenyl)malonate

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

56341-37-8

6-chloro-2-oxindole

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

4-chloro-2-nitro-phenylacetic acid

A

28230-26-4

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

B

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
588-07-8

3-Chloroacetanilide

623-48-3

ethyl iodoacetae

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%
2564-05-8

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

A

20870-77-3

4-chloroindolin-2-one

B

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;
879-32-3

6-chloroisatin 3-hydrazone

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;
89-61-2

2,5-dichloronitrobenzene

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
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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