5-Bromoisatin

5-Bromoisatin
  • CAS No.:87-48-9
Other grades of this product :
5-Bromoisatin Basic information
Product Name:5-Bromoisatin
Synonyms:5-Bromoindoline-2,3-dione, tech;5 - broMine indigo red;5-Bromoisatin technical grade, 90%;NSC 4980;5-BroMoisatin , 96.0%(LC&T;5-BROMO-1H-INDOLE-2,3-DIONE;5-BROMOISATIN;5-BROMOISATIN HEMIHYDRATE
CAS:87-48-9
MF:C8H4BrNO2
MW:226.03
EINECS:201-747-7
Product Categories:Indoles;Aromatics;Indole/indoline/oxindole;Indole and Indoline;Indane/Indanone and Derivatives;Heterocycles;Simple Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks
Mol File:87-48-9.mol
5-Bromoisatin Chemical Properties
Melting point 247-252 °C (lit.)
density 1.7498 (rough estimate)
refractive index 1.6120 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in N,N dimethylformamide.
pka8.74±0.20(Predicted)
form Crystalline Powder
color Orange
BRN 383760
InChIKeyMBVCESWADCIXJN-UHFFFAOYSA-N
CAS DataBase Reference87-48-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 37/38-41
Safety Statements 26-36/39-37/39-36
RIDADR 2811
WGK Germany 2
RTECS NL7875000
Hazard Note Irritant
HS Code 29337900
MSDS Information
ProviderLanguage
5-Bromoindoline-2,3-dione English
SigmaAldrich English
5-Bromoisatin Usage And Synthesis
Chemical PropertiesOrange crystalline powder
UsesIndole derivative
Uses5-Bromoisatin is used in the synthesis of N-derivatives of 5-bromoisatin, N-substituted pyrroles, linear polyaryleneoxindoles, 5-bromodioxindole, cinchoninic acid derivatives, 3-hydroxyoxindole, S-benzyldithiocarbazate Schiff Bases, 5-bromooxindole and Morita-Baylis-Hillman adducts of isatin derivatives. It is an indole derivative.
Synthesis Reference(s)Tetrahedron Letters, 25, p. 3099, 1984 DOI: 10.1016/0040-4039(84)80017-9
General Description5-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.
Purification Methods5-Bromoisatin forms red prisms or needles from EtOH. The N-acetate crystallises as yellow prisms from *C6H6, m 170-172o, and the N-methyl derivative forms orange-red needles from MeOH, m 172-173o. [Heller Chem Ber 53 1545 1920, Buu-Hoi Recl Trav Chim, Pays-Bas 73 197 1954, Baker etal. Tetrahedron Lett 215 1978, Beilstein 21 H 453, 21 III/IV 5009.]

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