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CS-W001157 4
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2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS No. 214360-62-0

  • Cat. No. CS-W010032
  • Purity≥97%
  • MDL No.MFCD03412794

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

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W010032

Structure of 214360-62-0

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General Information

  • CAS No. 214360-62-0
  • Cat. No. CS-W010032
  • Purity ≥97%
  • MDL No. MFCD03412794
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BBrNO₂
  • Molecular Weight None
  • Synonym(s) pyridine, 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
  • SMILES CC1(C)C(C)(C)OB(C2=CN=C(Br)C=C2)O1

Description

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group flanked by tetramethyl-substituted dioxaborolane rings, providing enhanced stability and moisture tolerance. This bench-stable reagent integrates readily into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The pyridine scaffold offers directional control in heterocyclic synthesis, while the bromide facilitates selective functionalization.

Application

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The pyridine core enables direct functionalization at the 5-position, while the stable, air-tolerant boronate ester facilitates efficient C–C bond formation with aryl and heteroaryl halides. Its bench-stable nature and compatibility with diverse reaction conditions make it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 14 p. 2885 - 2890
  • Route2

    References

    • Organic Letters, , vol. 15, # 6 p. 1346 - 1349
  • Route3

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 14 p. 2885 - 2890

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 : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   31.35
  • LogP   2.1433
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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