| Identification | More | [Name]
6-Bromoisatin | [CAS]
6326-79-0 | [Synonyms]
6-BROMO-1H-INDOLE-2,3-DIONE
6-BROMOINDOLE-2,3-DIONE
6-BROMOINDOLINE-2,3-DIONE
6-BROMOISATIN
6-BROMO ISATINIC ANHYDRIDE
AKOS B018432
BROMOISATIN(6-)
BUTTPARK 50\07-95
AKOS B01843
6-Bromoisatin 97%
6-BROMO-1H-INDOLE-2,3-DIONE 97.0%(MIN)(HPLC)
6-BROMOISATINMONOHYDRATE | [EINECS(EC#)]
678-162-2 | [Molecular Formula]
C8H4BrNO2 | [MDL Number]
MFCD01631138 | [Molecular Weight]
226.03 | [MOL File]
6326-79-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Orange Powder | [Melting point ]
274°C | [density ]
1.826±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
8.83±0.20(Predicted) | [color ]
Dark Yellow | [Usage]
Antimicrobial | [InChI]
InChI=1S/C8H4BrNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12) | [InChIKey]
HVPQMLZLINVIHW-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(Br)=C2)C(=O)C1=O | [CAS DataBase Reference]
6326-79-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
22-41-43 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
Orange Powder | [Uses]
Antimicrobial | [Biological Functions]
6-Bromoisatin inhibited proliferation of HT29 cells at IC50 223 μM (0.05 mg/mL) and induced apoptosis without increasing caspase 3/7 activity. In vivo 6-bromoisatin (0.05 mg/g) was found to significantly enhance the apoptotic index (p ≤ 0.001) and reduced cell proliferation (p ≤ 0.01) in the distal colon.
| [Synthesis]
Step 2: N-(3-bromophenyl)-2-hydroxyiminoacetamide (55 g, 0.2272 mol) was added to concentrated sulfuric acid (275 mL) and the temperature was maintained at 50 °C. The temperature of the reaction system was then raised to 90 °C for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and a yellow precipitate was precipitated. The precipitate was collected by filtration and dried to give 6-bromodihydroindole-2,3-dione as a yellow solid (50 g, 98% yield). The resulting product can be used directly in the subsequent reaction without further purification. | [Purification Methods]
6-Bromoisatin recrystallises from AcOH (yellow needles). It is a plant growth substance. IR in CHCl3 has 1320 and 3440cm-1. [Sadler J Org max Chem 21 169 1956, Beilstein 21 III/IV 5012.] | [References]
[1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 91
[2] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 36-37
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 549 - 554
[4] Medicinal Chemistry, 2014, vol. 10, # 5, p. 484 - 496
[5] Patent: US2014/38952, 2014, A1. Location in patent: Page/Page column 0154-0155 |
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