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CS-W001157 4
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3-Amino-5-bromo-2-methylpyridine

  • CAS No. 914358-73-9

  • Cat. No. CS-W003575
  • Purity≥95%
  • MDL No.MFCD09031418

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

3-Amino-5-bromo-2-methylpyridine|CS-W003575

Structure of 914358-73-9

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General Information

  • CAS No. 914358-73-9
  • Cat. No. CS-W003575
  • Purity ≥95%
  • MDL No. MFCD09031418
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇BrN₂
  • Molecular Weight 187.04
  • Synonym(s) 3ABMP
  • SMILES BrC1=CN=C(C)C(N)=C1

Description

3-Amino-5-bromo-2-methylpyridine features a strategically positioned amino group and bromine atom on a pyridine scaffold, enabling selective functionalization in cross-coupling reactions. The methyl substituent enhances electronic modulation and solubility, supporting efficient integration into pharmaceutical intermediates and advanced materials under standard conditions.

Application

3-Amino-5-bromo-2-methylpyridine serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling direct functionalization at multiple sites. The amino group facilitates nucleophilic substitution and coupling reactions, while the bromo substituent supports palladium-catalyzed cross-coupling transformations. Its methyl group enhances metabolic stability and modulates electronic properties. This compound exhibits excellent bench stability and is readily purified by recrystallization or column chromatography, making it ideal for scalable synthesis of pyridine-based pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • MERCK SHARP and DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan Patent: WO2014/28589 A2, 2014 ; Location in patent: Page/Page column 108 ;
  • Route2
    • Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate|CS-0541094
      911434-04-3
    • ~%
    • In-stock
      3-Amino-5-bromo-2-methylpyridine|CS-W003575
      914358-73-9

    References

    • Journal of Medicinal Chemistry, , vol. 54, # 6 p. 1789 - 1811
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 54, # 6 p. 1789 - 1811

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   38.91
  • LogP   1.73472
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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