2-Bromo-5-phenylpyridine

Name: 2-Bromo-5-phenylpyridine
Brand: ChemScene
Availability: InStock
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CAS No. 107351-82-6
Cat. No. CS-0018829
Purity≥97%
MDL No.MFCD04114195

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 107351-82-6

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General Information

CAS No. 107351-82-6
Cat. No. CS-0018829
Purity ≥97%
MDL No. MFCD04114195
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₈BrN
Molecular Weight 234.09
Synonym(s) Pyridine,2-bromo-5-phenyl
SMILES BrC1=NC=C(C2=CC=CC=C2)C=C1

Description

2-Bromo-5-phenylpyridine features a phenyl-substituted pyridine core with a bromine atom at the 2-position, enabling direct functionalization in cross-coupling reactions. The electron-deficient pyridine ring enhances reactivity in palladium-catalyzed transformations, while the ortho-bromo substitution facilitates selective C–C bond formation. This bench-stable, moisture-tolerant scaffold serves as a key building block for pharmaceutical intermediates and functional materials.

Application

2-Bromo-5-phenylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under standard Suzuki, Stille, and Negishi conditions. The bromine substituent exhibits high reactivity with palladium catalysts, while the phenylpyridine scaffold provides structural rigidity and favorable electronic properties for further functionalization. Bench-stable and readily purified by recrystallization, it functions effectively in the synthesis of biaryl motifs and complex heterocyclic systems relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  73290-22-9
- In-stock
  
  98-80-6
- ~92%
- In-stock
  
  107351-82-6
References
- WO2005/92304 A2, ; Page/Page column 42 ;
Route2
- In-stock
  
  33421-40-8
- ~88%
- In-stock
  
  107351-82-6
References
- Journal of the American Chemical Society, , vol. 131, p. 3621 - 3630
Route3
- In-stock
  
  624-28-2
- In-stock
  
  98-80-6
- ~12%
- In-stock
  
  27012-25-5
- In-stock
  
  107351-82-6
References
- Tetrahedron, , vol. 69, # 51 p. 10996 - 11003

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 12.89
LogP 3.5111
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-5-phenylpyridine

CAS No. 107351-82-6

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