3-Bromo-5-chloro-1H-indazole

Name: 3-Bromo-5-chloro-1H-indazole
Brand: ChemScene
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CAS No. 885521-43-7
Cat. No. CS-0041818
Purity≥97%
MDL No.MFCD07781584

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Structure of 885521-43-7

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General Information

CAS No. 885521-43-7
Cat. No. CS-0041818
Purity ≥97%
MDL No. MFCD07781584
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrClN₂
Molecular Weight 231.48
Synonym(s) 3-BROMO-5-CHLORO (1H)INDAZOLE
SMILES ClC1=CC2=C(NN=C2Br)C=C1

Description

3-Bromo-5-chloro-1H-indazole is a halogenated indazole scaffold featuring complementary reactive sites for cross-coupling and functionalization. The bromine at C3 and chlorine at C5 enable selective transformations under palladium catalysis, while the fused heterocyclic core provides planar rigidity and enhanced solubility in polar aprotic solvents. This structure serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and CNS-active compounds.

Application

3-Bromo-5-chloro-1H-indazole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the chloro substituent offers enhanced stability and orthogonal reactivity. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

Route1
- In-stock
  
  698-26-0
- ~61%
- In-stock
  
  885521-43-7
References
- Lohou, Elodie; Collot, Valeri; Stiebing, Silvia; Rault, Sylvain Synthesis, 2011 , # 16 art. no. Z42211SS, p. 2651 - 2663

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 28.68
LogP 2.9788
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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3-Bromo-5-chloro-1H-indazole

CAS No. 885521-43-7

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