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.

pka

8.74±0.20(Predicted)

form 

Crystalline Powder

color 

Orange

BRN 

383760

InChIKey

MBVCESWADCIXJN-UHFFFAOYSA-N

CAS DataBase Reference

87-48-9(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

• Language:English Provider:5-Bromoindoline-2,3-dione
• Language:English Provider:SigmaAldrich

5-Bromoisatin Usage And Synthesis

Chemical Properties

Orange crystalline powder

Uses

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.]

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