3-Methyl-1H-indazol-6-amine

Name: 3-Methyl-1H-indazol-6-amine
Brand: ChemScene
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CAS No. 79173-62-9
Cat. No. CS-0058667
Purity≥97%
MDL No.MFCD11007871

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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 79173-62-9

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General Information

CAS No. 79173-62-9
Cat. No. CS-0058667
Purity ≥97%
MDL No. MFCD11007871
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₉N₃
Molecular Weight 147.18
Synonym(s) CC1=NNC2=C1C=CC(N)=C2
SMILES NC1=CC2=C(C=C1)C(C)=NN2

Description

3-Methyl-1H-indazol-6-amine features a fused bicyclic indazole core with a methyl group at the 3-position and a primary amine at the 6-position. This configuration supports hydrogen bonding and π-stacking interactions, enhancing binding affinity in kinase inhibition studies. The compound exhibits bench-stable behavior under standard conditions and integrates readily into medicinal chemistry campaigns targeting ATP-binding sites.

Application

3-Methyl-1H-indazol-6-amine serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles through standard coupling reactions. Its ortho-amino functionality facilitates palladium-catalyzed cross-couplings and electrophilic substitutions, while the methyl group enhances metabolic stability. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it suitable for iterative synthetic approaches in API development.

Synthesis

Route1
- In-stock
  
  6494-19-5
- ~90%
- In-stock
  
  79173-62-9
References
- Harris, Philip A.; Boloor, Amogh; Cheung, Mui; Kumar, Rakesh; Crosby, Renae M.; Davis-Ward, Ronda G.; Epperly, Andrea H.; Hinkle, Kevin W.; Hunter III, Robert N.; Johnson, Jennifer H.; Knick, Victoria B.; Laudeman, Christopher P.; Luttrell, Deirdre K.; Mook, Robert A.; Nolte, Robert T.; Rudolph, Sharon K.; Szewczyk, Jerzy R.; Truesdale, Anne T.; Veal, James M.; Wang, Liping; Stafford, Jeffrey A. Journal of Medicinal Chemistry, 2008 , vol. 51, # 15 p. 4632 - 4640
Route2
- In-stock
  
  315203-37-3
- ~%
- In-stock
  
  79173-62-9
References
- WO2007/95124 A2, ; Page/Page column 61-62 ;

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 54.7
LogP 1.45352
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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3-Methyl-1H-indazol-6-amine

CAS No. 79173-62-9

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