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

Name: 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 452972-13-3
Cat. No. CS-0041166
Purity≥97%
MDL No.MFCD06798248

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3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0041166

Structure of 452972-13-3

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General Information

CAS No. 452972-13-3
Cat. No. CS-0041166
Purity ≥97%
MDL No. MFCD06798248
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BBrNO₂
Molecular Weight 283.96
Synonym(s) 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
SMILES CC1(C)C(C)(C)OB(C2=CN=CC(Br)=C2)O1

Description

3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group paired with a bromopyridine handle, enabling efficient Suzuki-Miyaura coupling under standard conditions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic media. This bifunctional building block integrates seamlessly into complex heterocyclic architectures, streamlining the synthesis of conjugated systems for pharmaceutical and materials applications.

Application

3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile Suzuki-Miyaura coupling building block, combining a readily displaced bromide with a stable boronate ester. Its orthogonal reactivity enables sequential functionalization in complex molecule assembly. The tetramethylcyclopentadienone-derived boronate offers excellent bench stability, minimal protodeboronation, and compatibility with diverse reaction conditions. Ideal for constructing biaryl scaffolds and heterocyclic frameworks in medicinal chemistry and materials science workflows.

Synthesis

Route1
- In-stock
  
  625-92-3
- In-stock
  
  76-09-5
- ~73%
- In-stock
  
  452972-13-3
References
- Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R.; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 17 p. 3323 - 3328
Route2
- In-stock
  
  625-92-3
- 61676-62-8
- ~16%
- In-stock
  
  452972-13-3
References
- Peters, Martin; Trobe, Melanie; Breinbauer, Rolf Chemistry - A European Journal, 2013 , vol. 19, # 7 p. 2450 - 2456
Route3
- In-stock
  
  76-09-5
- ~%
- In-stock
  
  452972-13-3
References
- Peters, Martin; Trobe, Melanie; Breinbauer, Rolf Chemistry - A European Journal, 2013 , vol. 19, # 7 p. 2450 - 2456

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
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 31.35
LogP 2.1433
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

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

CAS No. 452972-13-3

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