6-Bromo-1-methyl-1H-indazole

Name: 6-Bromo-1-methyl-1H-indazole
Brand: ChemScene
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CAS No. 590417-94-0
Cat. No. CS-D0266
Purity≥98%
MDL No.MFCD09878569

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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 590417-94-0

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General Information

CAS No. 590417-94-0
Cat. No. CS-D0266
Purity ≥98%
MDL No. MFCD09878569
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrN₂
Molecular Weight 211.06
Synonym(s) 1H-Indazole, 6-bromo-1-methyl-
SMILES CN1N=CC2=CC=C(C=C12)Br

Description

6-Bromo-1-methyl-1H-indazole is a brominated indazole derivative featuring a methyl group at the nitrogen and a bromine substituent at the C6 position. This configuration imparts enhanced electrophilicity and facilitates coupling reactions in synthetic applications. The molecule exhibits high stability under standard conditions, enabling reliable use in transition metal-catalyzed transformations and medicinal chemistry research.

Application

6-Bromo-1-methyl-1H-indazole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo group and electron-deficient indazole core. The methyl substituent enhances solubility and metabolic stability, while the scaffold is widely employed in constructing kinase inhibitors and other bioactive heterocycles. Its bench-stable nature and compatibility with standard coupling protocols facilitate efficient synthesis of complex molecular architectures.

Synthesis

Route1
- 74-88-4
- ~49%
- In-stock
  
  590417-94-0
- In-stock
  
  590417-95-1
References
- WO2007/84451 A1, ; Page/Page column 142 ; WO 2007/084451 A1
Route2
- 60-34-4
- In-stock
  
  57848-46-1
- ~49%
- In-stock
  
  590417-94-0
References
- Wheeler, Rob C.; Baxter, Emma; Campbell, Ian B.; MacDonald, Simon J. F. Organic Process Research and Development, 2011 , vol. 15, # 3 p. 565 - 569

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 17.82
LogP 2.3358
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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6-Bromo-1-methyl-1H-indazole

CAS No. 590417-94-0

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