| Identification | More | [Name]
6-Chlorooxindole | [CAS]
56341-37-8 | [Synonyms]
6-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE
6-CHLORO-1,3-DIHYDRO-INDOL-2-ONE
6-CHLORO-2-INDOLINONE
6-CHLORO-2-OXINDOLE
6-CHLORO-2-OXOINDOLINE
6-CHLOROINDOL-2(3H)-ONE
6-CHLOROOXINDOLE
AKOS 207-09
LABOTEST-BB LT01147821
6-Chloroindole-2(3H)-one
6-Chloro-2-oxoindole
6-Chloro-1,3-dihydro-2H-indol-
6-Chlorooxindole 98%
6-CHLOROOXINDOLE
6-Chloro-1,3-dihydroindole-2-one | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C8H6ClNO | [MDL Number]
MFCD00209962 | [Molecular Weight]
167.59 | [MOL File]
56341-37-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to tan crystalline powder | [Melting point ]
195-199 °C (lit.) | [Boiling point ]
329.0±42.0 °C(Predicted) | [density ]
1.362±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Dimethylformamide | [form ]
powder to crystal | [pka]
13.39±0.20(Predicted) | [color ]
Light yellow to Brown | [InChI]
InChI=1S/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11) | [InChIKey]
CENVPIZOTHULGJ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(Cl)=C2)CC1=O | [CAS DataBase Reference]
56341-37-8(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Preparation]
STEP A:
3-(2-nitro-4-chlorophenyl)pyruvic acid
To a cooled mixture prepared by adding 13.6 g. of
sodium to 300 ml. of ethanol is added a solution of 100
g. of 4-chloro-2-nitrotoluene and 84 g of diethyloxalate
in 150 ml of ethanol while maintaining the temperature
below 20℃. The resulting mixture is refluxed for one
hour, cooled, 400 ml. of water added and the resulting
mixture refluxed for 90 minutes. The ethanol is then
evaporated to a small volume and the resulting precipi
tate containstan and black material and the black mate
rial is mechanically separated and discarded and the
remainder (filtrate plus tan precipitate) used in the next
step. STEP B:
4-chloro-2-nitro-phenylacetic acid
The filtrate of Step A, above, is adjusted to pH 8-9
with 2 N sodium hydroxide and is heated at 35-40℃.
while adding a 3-6% aqueous hydrogen peroxide solution until samples no longer turn dark on treatment with
2N sodium hydroxide. The tan precipitate is suspended
in 1500 ml of water, adjusted to pH 8-9 and similarly
treated with aqueous hydrogen peroxide. The combined
reaction mixtures are then acidified with concentrated
hydrochloride acid to obtain a precipitate which are re
covered by filtration, washed 3 times with water and
dried in vacuo. The crude product (mp 145-150° C) is
recrystallized from ether to obtain 4-chloro-2-nitro
phenylacetic acid, m.p. 156-159℃. STEP C: The product of Step B, above, is subjected to reductive
cyclization analogously to Step B of Example 1 to
obtain 6-chloro-oxindole, m.p. 185-189℃. |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H317 | [Precautionary statements ]
P280-P301+P312+P330-P302+P352 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [REACH Registrations]
Active | [HS Code ]
29337900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Sens. 1 |
| Hazard Information | Back Directory | [Description]
6-Chlorooxindole is an organic compound that has been used in the pharmaceutical industry as a hydrogen bond donor and a dihydrate salt. It is an aromatic heterocycle with two rings, one of which is an oxindole ring. 6-Chlorooxindole has been shown to be stable at low pH and high temperatures, with the exception of hydrochloric acid. It is also soluble in water and can be prepared in a variety of ways, including by reacting benzene with nitrous acid or by heating oxindole with sodium hydroxide. 6-Chlorooxindole can be found as a component in some pharmaceutical preparations such as carbamazepine and ziprasidone. It can also be found as a component of the drug chlorpromazine. | [Chemical Properties]
Off-white to tan crystalline powder | [Uses]
6-Chlorooxindole is a useful research chemical used in the design of potent non-peptide MDM2 inhibitors. | [Application]
6-chlorooxyindole, also known as 6-chloro-2-indolone, is an intermediate of Ziprasidone hydrochloride. Ziprasidone is an atypical broad-spectrum antipsychotic developed by Pfizer for the treatment of schizophrenia with a strong affinity for serotonin and dopamine receptor antagonists, particularly the 5-HTA2/DAD2 receptor. | [Definition]
ChEBI: 6-Chlorooxindole is a member of indoles. | [Synthesis]
GENERAL PROCEDURE: TiCl4 (0.7 mL, 6 mmol) was added dropwise to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshly distilled anhydrous THF (15 mL) at room temperature and under a dry N2 atmosphere. After addition, the mixture was refluxed for 2 hours. After the formed suspension of low-valent titanium reagent was cooled, a solution of 6-chloroindole-2,3-dione (2 mmol) in THF (10 mL) was slowly added. The mixture was stirred at room temperature for about 5 min under N2 protection. Subsequently, the completion of the reaction was confirmed by thin layer chromatography (TLC) analysis. The reaction mixture was quenched with 3% HCl (15 mL) and extracted with CHCl3 (3 x 50 mL). The organic phases were combined, washed with water (3 x 50 mL) and dried over anhydrous Na2SO4. After concentration of the solvent under reduced pressure, the crude product was purified by column chromatography (petroleum ether/ethyl acetate = 5:1) to give 6-chlorooxindole. | [References]
[1] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2238 - 2242
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042
[3] Patent: US4658037, 1987, A
[4] Patent: US4652658, 1987, A
[5] Patent: US4730004, 1988, A |
|
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J & K SCIENTIFIC LTD.
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https://www.jkchemical.com |
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Alfa Aesar
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http://chemicals.thermofisher.cn |
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Energy Chemical
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400-0056266 |
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www.energy-chemical.com |
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