4-Bromo-1H-indole-2,3-dione

Name: 4-Bromo-1H-indole-2,3-dione
Brand: ChemScene
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CAS No. 20780-72-7
Cat. No. CS-W008631
Purity≥98%
MDL No.MFCD03618555

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Description

4-Bromo-1H-indole-2,3-dione features a brominated indole core with two carbonyl groups, offering enhanced electrophilicity and stability under standard conditions. This electron-deficient scaffold integrates readily into heterocyclic systems, enabling efficient coupling in transition-metal-catalyzed reactions. The para-bromine facilitates direct functionalization, streamlining access to complex molecular architectures.

Application

4-Bromo-1H-indole-2,3-dione serves as a versatile building block in heterocyclic synthesis, enabling efficient access to functionalized indole derivatives through palladium-catalyzed cross-coupling reactions. Its brominated position facilitates direct substitution under standard Suzuki, Stille, or Negishi conditions, while the quinone functionality supports electrophilic transformations and Diels-Alder cycloadditions. The compound exhibits excellent bench stability and simplifies purification due to its crystalline nature, making it well-suited for iterative synthesis workflows in medicinal chemistry and materials science.

General Information

CAS No. 20780-72-7
Cat. No. CS-W008631
Purity ≥98%
MDL No. MFCD03618555
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₄BrNO₂
Molecular Weight 226.03
Synonym(s) 4-Bromoindole-2,3-dione; 4-Bromoindoline-2,3-dione; 4-Bromoisatin; 4-Bromo-2,3-indolinedione
SMILES O=C1NC2=C(C(Br)=CC=C2)C1=O

Computational Chemistry Data

TPSA 46.17
LogP 1.5839
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Indolin compounds

Key Words

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4-Bromo-1H-indole-2,3-dione

CAS No. 20780-72-7

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