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2-Bromo-5-(difluoromethyl)pyridine

  • CAS No. 1221272-81-6

  • Cat. No. CS-0130419
  • Purity≥95%
  • MDL No.None

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

2-Bromo-5-(difluoromethyl)pyridine|CS-0130419

Structure of 1221272-81-6

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General Information

  • CAS No. 1221272-81-6
  • Cat. No. CS-0130419
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄BrF₂N
  • Molecular Weight 208.00
  • Synonym(s) 6-Bromo-3-(dimethyl)pyridine
  • SMILES FC(F)C1=CN=C(C=C1)Br

Description

2-Bromo-5-(difluoromethyl)pyridine features a strategically positioned difluoromethyl group that enhances metabolic stability and modulates electronic properties. This bench-stable heterocycle integrates readily into cross-coupling reactions, serving as a key building block for fluorinated pharmaceutical intermediates and functional materials.

Application

2-Bromo-5-(difluoromethyl)pyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-defined electrophilic bromide and ortho-directing pyridine nitrogen. The difluoromethyl group imparts enhanced metabolic stability and modulates electronic properties, facilitating integration into bioactive scaffolds. Its bench-stable nature and compatibility with common protecting groups support efficient synthesis workflows.

Synthesis

  • Route1

    References

    • Lemoine, Remy C.; Petersen, Ann C.; Setti, Lina; Jekle, Andreas; Heilek, Gabrielle; Derosier, Andre; Ji, Changhua; Berry, Pamela; Rotstein, David M. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 16 p. 4753 - 4756

Safety Information

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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   12.89
  • LogP   2.7817
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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