5-Bromo-3-iodo-7-azaindole

Name: 5-Bromo-3-iodo-7-azaindole
Brand: ChemScene
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CAS No. 757978-18-0
Cat. No. CS-W019651
Purity≥95%
MDL No.MFCD07779519

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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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Structure of 757978-18-0

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General Information

CAS No. 757978-18-0
Cat. No. CS-W019651
Purity ≥95%
MDL No. MFCD07779519
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrIN₂
Molecular Weight 322.93
Synonym(s) 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine
SMILES IC1=CNC2=NC=C(Br)C=C21

Description

5-Bromo-3-iodo-7-azaindole features a sterically accessible core with complementary halogen handles enabling efficient cross-coupling. The electron-deficient 7-azaindole scaffold enhances reactivity in Pd-catalyzed transformations, while the bromo and iodo substituents allow sequential functionalization under mild conditions. This dual-halogenated heterocycle serves as a pivotal building block for complex molecular architectures in medicinal chemistry and materials science.

Application

5-Bromo-3-iodo-7-azaindole serves as a versatile building block for the construction of functionalized heterocycles in medicinal chemistry and materials science. The strategic placement of bromo and iodo substituents enables sequential cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with high chemoselectivity and excellent functional group tolerance. Bench-stable and readily purified by column chromatography, it functions as a key intermediate in the synthesis of complex azaindole-based scaffolds relevant to pharmaceutical development.

Synthesis

Route1
- In-stock
  
  183208-35-7
- ~99%
- In-stock
  
  757978-18-0
References
- UNIVERSITY OF ROCHESTER; BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA; GELBARD, Harris A.; DEWHURST, Stephen; GENDELMAN, Howard E. Patent: WO2014/85795 A1, 2014 ; Location in patent: Paragraph 0400 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 1759
Class : 8	Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 28.68
LogP 2.93
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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5-Bromo-3-iodo-7-azaindole

CAS No. 757978-18-0

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