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6-Bromoisatin

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CAS:6326-79-0
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Products Intro: Product Name:6-Bromoisatin
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  • CAS:6326-79-0
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  • 6-Bromoisatin
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  • 2025-05-23
  • CAS:6326-79-0
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6-Bromoisatin Basic information
Product Name:6-Bromoisatin
Synonyms:BUTTPARK 50\07-95;BROMOISATIN(6-);6-BROMOINDOLE-2,3-DIONE;6-BROMOINDOLINE-2,3-DIONE;6-BROMOISATIN;6-BROMO ISATINIC ANHYDRIDE;6-BROMO-1H-INDOLE-2,3-DIONE;AKOS B018432
CAS:6326-79-0
MF:C8H4BrNO2
MW:226.03
EINECS:678-162-2
Product Categories:Heterocyclic Compounds;Indoles;Simple Indoles;Heterocycles;Phenyls & Phenyl-Het;Fused Ring Systems;Indane/Indanone and Derivatives;Halides;Aminomethyl's;Phenyls & Phenyl-Het
Mol File:6326-79-0.mol
6-Bromoisatin Structure
6-Bromoisatin Chemical Properties
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
pka8.83±0.20(Predicted)
color Dark Yellow
InChIInChI=1S/C8H4BrNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12)
InChIKeyHVPQMLZLINVIHW-UHFFFAOYSA-N
SMILESN1C2=C(C=CC(Br)=C2)C(=O)C1=O
CAS DataBase Reference6326-79-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 22-41-43
Safety Statements 22-24/25-36/37/39-26
HazardClass IRRITANT
HS Code 2933998090
MSDS Information
6-Bromoisatin Usage And Synthesis
Chemical PropertiesOrange Powder
UsesAntimicrobial
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
Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-

65971-74-6

6-Bromoisatin

6326-79-0

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 Methods6-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
Tag:6-Bromoisatin(6326-79-0) Related Product Information
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