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Methyl 2-methyl-2H-indazole-3-carboxylate

  • CAS No. 109216-61-7

  • Cat. No. CS-0097672
  • Molecule weight190.20
  • Purity≥97%
  • MDL No.None

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

Methyl 2-methyl-2H-indazole-3-carboxylate|CS-0097672

Structure of 109216-61-7

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General Information

  • CAS No. 109216-61-7
  • Cat. No. CS-0097672
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀N₂O₂
  • Molecular Weight 190.20
  • Synonym(s) methyl 2-methylindazole-3-carboxylate
  • SMILES O=C(C1=C2C=CC=CC2=NN1C)OC

Description

Methyl 2-methyl-2H-indazole-3-carboxylate features a sterically hindered indazole core with a methyl group at the 2-position, enhancing stability and modulating electronic properties. The ester functionality enables direct use in cross-coupling reactions or hydrolysis to access carboxylic acid derivatives. This compound serves as a key intermediate in medicinal chemistry for developing kinase inhibitors and bioactive heterocycles.

Application

Methyl 2-methyl-2H-indazole-3-carboxylate serves as a versatile building block for the synthesis of indazole-based pharmaceuticals and agrochemicals. The ester group enables straightforward derivatization, while the 2-methyl substitution enhances stability and modulates reactivity. It functions effectively in Pd-catalyzed cross-coupling reactions and participates in electrophilic functionalization at the C2 position, offering reliable access to substituted indazoles under standard bench conditions.

Synthesis

  • Route1
    • In-stock
      Methyl 1H-indazole-3-carboxylate|CS-W020527
      43120-28-1
    • null|null
      74-88-4
    • ~%
    • In-stock
      Methyl 2-methyl-2H-indazole-3-carboxylate|CS-0097672
      109216-61-7

    References

    • AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A. Patent: WO2008/61688 A1, 2008 ; Location in patent: Page/Page column 20 ; WO 2008/061688 A1
  • Route2

    References

    • Vishnu, Eda V.R.; Joseph, Suju; Srinivasana, Abayee K.; Gania, Ramesh S.; Reddy, Govindabur R.; Rao, Patakokila V.; Dahanukara, Vilas H.; Ramanatham, Josyula; Devanna, Nayakanti Letters in Organic Chemistry, 2011 , vol. 8, # 10 p. 722 - 727
  • Route3
    • null|null
      74-88-4
    • ~%
    • In-stock
      Methyl 2-methyl-2H-indazole-3-carboxylate|CS-0097672
      109216-61-7

    References

    • v. Auwers; Dereser Chemische Berichte, 1919 , vol. 52, p. 1345,1348

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   44.12
  • LogP   1.3599
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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