476994
5-Bromoisatin
technical grade, 90%
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About This Item
Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
Molecular Weight:
226.03
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-747-7
Beilstein/REAXYS Number:
383760
MDL number:
Product Name
5-Bromoisatin, technical grade, 90%
InChI key
MBVCESWADCIXJN-UHFFFAOYSA-N
InChI
1S/C8H4BrNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
SMILES string
Brc1ccc2NC(=O)C(=O)c2c1
grade
technical grade
assay
90%
impurities
<10% isatin
mp
247-252 °C (lit.)
functional group
bromo
ketone
Quality Level
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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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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 of isatin and 5-bromoisatin derivatives.
Mesropyan EG, et al.
Russ. J. Org. Chem., 37(10), 1476-1477 (2001)
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)
A green approach for efficient synthesis of N-substituted pyrroles in ionic liquid under microwave irradiation.
Meshram HM, et al.
Tetrahedron Letters, 51(27), 3477-3480 (2010)
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)
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