5-Bromoisatin

Chemical properties

Orange crystalline powder

The Uses of 5-Bromoisatin

5-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.

Definition

ChEBI: 5-Bromoisatin is a member of indoles. It has a role as an anticoronaviral agent.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3099, 1984 DOI: 10.1016/0040-4039(84)80017-9

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.

Purification Methods

5-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.]