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CS-W001157 4
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2-Amino-3-methylphenol

  • CAS No. 2835-97-4

  • Cat. No. CS-W001164
  • Purity≥95%
  • MDL No.MFCD00075082

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

2-Amino-3-methylphenol|CS-W001164

Structure of 2835-97-4

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General Information

  • CAS No. 2835-97-4
  • Cat. No. CS-W001164
  • Purity ≥95%
  • MDL No. MFCD00075082
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO
  • Molecular Weight 123.15
  • Synonym(s) 2-Hydroxy-6-methylaniline
  • SMILES Nc1c(C)cccc1O

Description

2-Amino-3-methylphenol serves as a key intermediate in pharmaceutical synthesis, featuring a strategically positioned amino group adjacent to a phenolic hydroxyl. This arrangement enables facile coupling reactions and facilitates incorporation into bioactive scaffolds. The methyl substituent enhances metabolic stability while maintaining favorable reactivity profiles under standard conditions.

Application

2-Amino-3-methylphenol serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling access to substituted heterocycles via cyclization and coupling reactions. Its ortho-diamine motif facilitates metal-catalyzed cross-coupling and oxidative aromatization, while the methyl group enhances metabolic stability. The compound exhibits good bench stability and is readily purified by crystallization or column chromatography, supporting its use in multi-step synthetic sequences requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1

    References

    • VICURON PHARMACEUTICALS INC. Patent: US2006/211603 A1, 2006 ; Location in patent: Page/Page column 68 ;
  • Route2

    References

    • Haga, Naoki; Endo, Yasuyuki; Kataoka, Ken-Ichiro; Yamaguchi, Kentaro; Shudo, Koichi Journal of the American Chemical Society, 1992 , vol. 114, # 25 p. 9795 - 9806
  • Route3
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    • ~%
    • In-stock
      2-Amino-3-methylphenol|CS-W001164
      2835-97-4

    References

    • Hodgson; Beard Journal of the Chemical Society, 1925 , vol. 127, p. 498

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352

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Computational Chemistry Data

  • TPSA   46.25
  • LogP   1.28282
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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