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CS-W001157 4
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6-Amino-5-bromonicotinic acid

  • CAS No. 180340-69-6

  • Cat. No. CS-W022442
  • Purity≥98%
  • MDL No.MFCD11109515

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

6-Amino-5-bromonicotinic acid|CS-W022442

Structure of 180340-69-6

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General Information

  • CAS No. 180340-69-6
  • Cat. No. CS-W022442
  • Purity ≥98%
  • MDL No. MFCD11109515
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) 6-Amino-5-bromopyridine-3-carboxylic acid
  • SMILES O=C(C1=CC(Br)=C(N)N=C1)O

Description

6-Amino-5-bromonicotinic acid features a brominated pyridine core with complementary amino and carboxylic acid functionalities. This electron-deficient heterocycle integrates readily into medicinal chemistry scaffolds, enabling direct coupling for peptide conjugation or transition metal-catalyzed functionalization under standard conditions.

Application

6-Amino-5-bromonicotinic acid serves as a versatile building block in medicinal chemistry, enabling direct incorporation into heterocyclic scaffolds via palladium-catalyzed cross-coupling or nucleophilic substitution. The ortho-halogen and amino groups provide complementary reactivity for sequential functionalization, while the carboxylic acid facilitates derivatization through amide or ester formation. Bench-stable and readily purified by recrystallization, it functions efficiently in multi-step syntheses of bioactive molecules requiring regiocontrolled substitution on the pyridine core.

Synthesis

  • Route1

    References

    • US5532235 A1, ; US 5532235 A US5654297 A1, ; US 5654297 A
  • Route2

    References

    • US2011/178053 A1, ; Page/Page column 25 ; US 20110178053 A1

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

Quality Control

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Computational Chemistry Data

  • TPSA   76.21
  • LogP   1.1245
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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