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476994

Sigma-Aldrich

5-Bromoisatin

technical grade, 90%

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About This Item

Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
87-48-9
Molecular Weight:
226.03
Beilstein:
383760
EC Number:
201-747-7
MDL number:
MFCD00005719
UNSPSC Code:
12352100
PubChem Substance ID:
24871320
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

impurities

<10% isatin

mp

247-252 °C (lit.)

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis of isatin and 5-bromoisatin derivatives.
Mesropyan EG, et al.
Russ. J. Org. Chem., 37(10), 1476-1477 (2001)
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)
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)
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