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Cas Database |
| Name |
6-Chlorooxindole |
EINECS | 1312995-182-4 |
| CAS No. | 56341-37-8 | Density | 1.362 g/cm3 |
| PSA | 29.10000 | LogP | 1.97260 |
| Solubility | N/A | 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 | N/A | Appearance | Off-white to tan crystalline powder |
| Safety | 37/39-36-26 | Risk Codes | 22-43-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xn,  Xi
|
| 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; |
Article Data | 30 |
6-Chlorooxindole Synthetic route
- 6341-92-0
6-chloroisatin
- 56341-37-8
6-chloro-2-oxindole
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride; tin In ethanol Heating; | 79% |
- 147124-32-1
dimethyl (4-chloro-2-nitrophenyl)malonate
- 56341-37-8
6-chloro-2-oxindole
| Conditions | Yield |
|---|---|
| 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; |
- 56341-37-8
6-chloro-2-oxindole
| Conditions | Yield |
|---|---|
| With hydrogen; acetic acid; Pt/C In water | 71% |
- 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
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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