ChemicalBook Product Catalog Organic Chemistry Heterocyclic Compounds 6-Bromoisatin

6-Bromoisatin

Product Name6-Bromoisatin
CAS6326-79-0
MFC8H4BrNO2
MW226.03
EINECS678-162-2
MOL File6326-79-0.mol

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
WGK Germany	WGK 3
HazardClass	IRRITANT
HS Code	2933998090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2

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

Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-

65971-74-6

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 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

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