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

pka

8.83±0.20(Predicted)

color 

Dark Yellow

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 Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41-43

Safety Statements 

22-24/25-36/37/39-26

HazardClass 

IRRITANT

HS Code 

2933998090

6-Bromoisatin Usage And Synthesis

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

6-Bromoisatin(6326-79-0)Related Product Information

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• 3-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine
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