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About This Item
Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
Molecular Weight:
226.03
Beilstein:
383760
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
technical grade
Quality Level
Assay
90%
impurities
<10% isatin
mp
247-252 °C (lit.)
functional group
bromo
ketone
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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J. Prakt. Chem., 322(2), 314-320 (1980)
V N Garalene et al.
Voprosy meditsinskoi khimii, 30(5), 56-59 (1984-09-01)
Effect of isatin and of three its derivatives on content of lactate, pyruvate and glycogen was studied in rat tissues. The substances studied, except of 5-butylisatin, decreased the content of lactic acid with simultaneous increase of glycogen content in liver
A facile one-pot method for the preparation of N-alkyl isatins under microwave irradiation.
Azizian J, et al.
Synthetic Communications, 33(5), 789-793 (2003)
Synthesis, characterization and cytotoxic activity of S-benzyldithiocarbazate Schiff bases derived from 5-fluoroisatin, 5-chloroisatin, 5-bromoisatin and their crystal structures.
Manan MAFA, et al.
Journal of Chemical Crystallography, 41(11), 1630-1641 (2011)
A practical large-scale preparation of 5'-bromospiro (cyclohexane-1,3-[3H] indol)-2'(1'H)-one.
Wilk BK, et al.
Organic preparations and procedures international, 37(3), 283-285 (2005)
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