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CS-W001157 4
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2-Methyl-2H-indazol-6-amine

  • CAS No. 50593-30-1

  • Cat. No. CS-0006054
  • Purity≥97%
  • MDL No.MFCD00464866

*For research and further manufacturing use only, not for direct human use.

2-Methyl-2H-indazol-6-amine|CS-0006054

Structure of 50593-30-1

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General Information

  • CAS No. 50593-30-1
  • Cat. No. CS-0006054
  • Purity ≥97%
  • MDL No. MFCD00464866
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉N₃
  • Molecular Weight 147.18
  • Synonym(s) 6-Amino-2-Methyl-2H-Indazole; 2-Methyl-2H-indazol-6-amine
  • SMILES NC1=CC2=NN(C)C=C2C=C1

Description

2-Methyl-2H-indazol-6-amine features a fused bicyclic indazole core with a methyl group at the 2-position and a primary amine at the 6-position. This configuration imparts enhanced solubility and reactivity in transition metal-catalyzed coupling reactions, enabling efficient incorporation into bioactive molecules and functional materials under mild conditions.

Application

2-Methyl-2H-indazol-6-amine serves as a versatile building block for medicinal chemistry, enabling rapid access to substituted indazole scaffolds via palladium-catalyzed cross-coupling reactions. Its ortho-amino functionality facilitates direct functionalization and cyclization pathways, while the methyl group enhances metabolic stability. The compound exhibits good bench stability and is readily purified by standard chromatographic methods, making it well-suited for high-throughput synthesis and API intermediate development.

Synthesis

  • Route1

    References

    • Qi, Haofei; Chen, Ligong; Liu, Bingni; Wang, Xinran; Long, Li; Liu, Dengke Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 4 p. 1108 - 1110
  • Route2

    References

    • Miloudi, Abdellah; El Abed, Douniazed; Boyer, Gerard; Galy, Jean-Pierre Heterocycles, 2006 , vol. 68, # 12 p. 2595 - 2605
  • Route3

    References

    • Boyer, Gerard; Galy, Jean-Pierre; Faure, Robert; Elguero, Jose; Barbe, Jacques Journal of Chemical Research, Miniprint, 1990 , # 11 p. 2601 - 2615

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   43.84
  • LogP   1.1555
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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