6-Bromooxindole CAS 99365-40-9
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Hazard Note | Irritant |
Introduction
6-Bromooxindole(6-Bromooxindole) is an organic compound with a chemical formula of C8H5BrNO and a white to light yellow crystalline appearance.
Here are some of the properties of 6-Bromooxindole:
-Melting point: 139-141°C
-Boiling point: 390-392°C
-Molecular weight: 216.04g/mol
-There may be an unbearably irritating odor.
6-Bromooxindole can be used in different reactions in organic synthesis, such:
-As an organic catalyst and ligand, it is used to catalyze the production of various organic compounds.
-As a pharmaceutical intermediate, used to synthesize certain biologically active compounds.
-As an organic light-emitting material, it can be used in the preparation of organic light-emitting diodes (OLEDs) and other devices.
The preparation method of 6-Bromooxindole includes the following reactions:
-Reaction of the indolone with bromine solution gives 6-Bromooxindole.
When dealing with 6-Bromooxindole, you need to pay attention to the following safety information:
-May cause irritation to the eyes, skin and respiratory tract. Wear appropriate protective equipment.
-Avoid inhalation or contact with skin to avoid allergy or irritation.
-in use should pay attention to good ventilation conditions, and keep the work area clean.
This information is for reference only. Please follow the laboratory's safety regulations and operating procedures when using and handling this compound.
Application
6-Bromooxindole (6-Bromo-1,3-dihydro-2H-indol-2-one, CAS 99365-40-9) is a halogenated oxindole building block widely used as a versatile intermediate in pharmaceutical research and organic synthesis. Its primary application is in the preparation of indolin-2-one p38α MAP kinase inhibitors, which have potential anti-inflammatory activity for treating rheumatoid arthritis, psoriasis, and other inflammatory diseases. The compound also serves as a valuable scaffold for synthesizing 1,3-disubstituted 2-oxindoles and other bioactive heterocyclic frameworks. Beyond medicinal chemistry, 6-bromooxindole functions as a sulfonylation reagent in drug discovery and organic synthesis, enabling the introduction of sulfonyl groups into target molecules. Its bromine substituent allows for further functionalization via cross-coupling reactions (Suzuki-Miyaura, Buchwald-Hartwig), facilitating the construction of complex molecular architectures. Additionally, the compound has demonstrated cytotoxicity against MDA-MB-231 breast cancer cells (IC₅₀ = 74.41 μM) and is utilized in biological research to study enzyme and receptor mechanisms. In materials science, its unique electronic properties are explored for organic semiconductors, dyes, and photonic devices. It is also employed as an analytical standard in HPLC/GC methods for quantifying related compounds in complex mixtures and in environmental science for pollutant degradation studies. High purity (≥97–99%) ensures reproducible results in SAR studies and GMP-compliant manufacturing.
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