| Identification | More | [Name]
6-Chloroisatin | [CAS]
6341-92-0 | [Synonyms]
6-CHLORO-1H-INDOLE-2,3-DIONE
6-CHLORO-2,3-INDOLINEDIONE
6-CHLOROINDOLE-2,3-DIONE
6-CHLOROISATIN
6-CHLORO ISATIN ANHYDRIDE
6-CHLORO ISATINIC ANHYDRIDE
BUTTPARK 50\07-92
6-CHLORO-1H-INDOLE-2,3-DIONE 97.0%(MIN)(HPLC) | [EINECS(EC#)]
676-145-4 | [Molecular Formula]
C8H4ClNO2 | [MDL Number]
MFCD00086347 | [Molecular Weight]
181.58 | [MOL File]
6341-92-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
262 °C | [density ]
1.519±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Dimethylformamide | [form ]
powder to crystal | [pka]
8.83±0.20(Predicted) | [color ]
Light yellow to Brown | [InChI]
InChI=1S/C8H4ClNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12) | [InChIKey]
RVXLBLSGEPQBIO-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(Cl)=C2)C(=O)C1=O | [CAS DataBase Reference]
6341-92-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Orange powder | [Uses]
6-Chloroisatin can be used as potential apoptosis inducer in non-small lung cancer AS49 cells. | [Synthesis]
Step 2: 6-Chloroindirubin 3,3-dibromo-6-chloro-1,3-dihydro-indol-2-one (21.34 g, 59.7 mmol) was suspended in a 4:1 (v:v) solvent mixture of methanol and water (172 mL of methanol and 43 mL of water) and heated and refluxed for 19 hours. Upon completion of the reaction, the mixture was cooled in an ice bath and subsequently filtered. The resulting red solid was washed once with cold methanol and dried to give 6-chloroindole-2,3-dione (10.49 g, 88% yield). The product was confirmed to be structurally consistent by NMR hydrogen spectroscopy (400 MHz, DMSO-d6). Mass spectrometry analysis (API-ES+) showed m/z 182/184 [M+H]+, consistent with a characteristic peak containing one chlorine atom. | [References]
[1] Patent: US2005/250798, 2005, A1. Location in patent: Page/Page column 26
[2] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7679 - 7682
[3] Tetrahedron Letters, 2002, vol. 43, # 26, p. 4671 - 4673 |
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