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476994

Sigma-Aldrich

5-Bromoisatin

technical grade, 90%

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About This Item

Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
87-48-9
Molecular Weight:
226.03
Beilstein:
383760
EC Number:
201-747-7
MDL number:
MFCD00005719
UNSPSC Code:
12352100
PubChem Substance ID:
24871320
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

impurities

<10% isatin

mp

247-252 °C (lit.)

SMILES string

Brc1ccc2NC(=O)C(=O)c2c1

InChI

1S/C8H4BrNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)

InChI key

MBVCESWADCIXJN-UHFFFAOYSA-N

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General description

5-Bromoisatin is a 5-haloisatin. One of the methods reported for its synthesis is by reacting N-halosaccharins with isatin in the presence of SiO2. Its inotropic activity has been studied on rhythmically stimulated papillary muscles of guinea pigs. It is reported to exhibit analgesic and sedative properties at a dose of 0.2g/kg in mice.

Application

5-Bromoisatin may be used in the synthesis of the following:
  • N-derivatives of 5-bromoisatin
  • N-substituted pyrroles
  • linear polyaryleneoxindoles
  • 5-bromodioxindole
  • cinchoninic acid derivatives
  • 3-hydroxyoxindole
  • S-benzyldithiocarbazate Schiff Bases
  • 5-bromooxindole
  • Morita-Baylis-Hillman adducts of isatin derivatives

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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V Garalene
Eksperimental'naia i klinicheskaia farmakologiia, 62(3), 20-24 (1999-08-10)
The inotropic activity of 5-bromisatin (5-bromindolyn-2,3-dion) which possesses antihypoxic properties was studied on rhythmically stimulated papillary muscles of guinea pigs, and the changes in the force of their contractions were recorded. The inotropic efficacy (calculated according to ED50 value) of
The Structures of the Bromodioxindoles of Baeyer and Knop.
Sumpter WC.
Journal of the American Chemical Society, 67(7), 1140-1141 (1945)
Synthesis and spectral data for cinchoninic acids.
Sarkis GY.
Journal of Chemical and Engineering Data, 17(3), 388-391 (1972)
Superelectrophiles in aromatic polymer chemistry.
Colquhoun HM, et al.
Macromolecules, 34(4), 1122-1124 (2001)
SiO2 mediated reaction of isatin with N-halosaccharins: A regiospecific preparation of 5-haloisatins.
de Souza SPL, et al.
Heterocyclic Communications, 9(1), 31-34 (2003)
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