4-Iodoindoline-2,3-dione

Name: 4-Iodoindoline-2,3-dione
Brand: ChemScene
Availability: InStock
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CAS No. 20780-75-0
Cat. No. CS-0108793
Purity≥98%
MDL No.MFCD03427300

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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+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 20780-75-0

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General Information

CAS No. 20780-75-0
Cat. No. CS-0108793
Purity ≥98%
MDL No. MFCD03427300
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₄INO₂
Molecular Weight 273.03
Synonym(s) 4-Iodo-1H-indole-2,3-dione
SMILES IC1=C2C(NC(C2=O)=O)=CC=C1

Description

4-Iodoindoline-2,3-dione serves as a reactive electrophilic scaffold for C–H functionalization and cross-coupling processes. The iodine atom enables efficient palladium-catalyzed transformations, while the fused diketone core provides rigidity and enhanced stability under standard conditions. This structure facilitates direct derivatization at the indoline nitrogen and adjacent positions, enabling rapid access to complex heterocyclic architectures in medicinal chemistry and materials science applications.

Application

4-Iodoindoline-2,3-dione serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable iodide functionality. The molecule’s electron-deficient indoline scaffold facilitates electrophilic functionalization and provides a robust platform for constructing complex heterocyclic frameworks. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for iterative synthesis and medicinal chemistry applications.

Synthesis

Route1
- 63608-68-4
- ~40%
- In-stock
  
  20780-77-2
- In-stock
  
  20780-75-0
References
- Katsifis, Andrew; Mattner, Filomena; McPhee, Meredith; Kassiou, Michael; Najdovski, Ljubco; Dikic, Branko Journal of Labelled Compounds and Radiopharmaceuticals, 1996 , vol. 38, # 9 p. 835 - 845
Route2
- In-stock
  
  626-01-7
- ~%
- In-stock
  
  20780-75-0
References
- Tetrahedron, , vol. 61, # 25 p. 6082 - 6087

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 46.17
LogP 1.426
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Skeleton Aromatic heterocycle compounds Indolin compounds

Key Words

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4-Iodoindoline-2,3-dione

CAS No. 20780-75-0

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