3-Bromo-5-phenylpyridine

Name: 3-Bromo-5-phenylpyridine
Brand: ChemScene
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CAS No. 142137-17-5
Cat. No. CS-W021876
Purity≥97%
MDL No.MFCD04114223

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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 142137-17-5

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General Information

CAS No. 142137-17-5
Cat. No. CS-W021876
Purity ≥97%
MDL No. MFCD04114223
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₈BrN
Molecular Weight 234.09
Synonym(s) None
SMILES BrC1=CC(C2=CC=CC=C2)=CN=C1

Description

3-Bromo-5-phenylpyridine features a phenyl-substituted pyridine core with a bromine atom at the 3-position, enabling direct functionalization in cross-coupling reactions. The electron-deficient aromatic system enhances reactivity in palladium-catalyzed transformations, while the sterically accessible site facilitates efficient coupling with diverse nucleophiles. This bench-stable building block integrates readily into complex molecular architectures for pharmaceutical and materials applications.

Application

3-Bromo-5-phenylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its bromine substituent facilitates reliable Suzuki, Stille, and Negishi couplings, while the phenyl group imparts enhanced stability and solubility. The molecule exhibits excellent bench stability and is readily purified by standard chromatographic methods, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  625-92-3
- In-stock
  
  98-80-6
- ~67%
- In-stock
  
  142137-17-5
References
- Chojnacka, Kinga; Papke, Roger L.; Horenstein, Nicole A. Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 14 p. 4145 - 4149
Route2
- In-stock
  
  625-92-3
- 110-71-4
- In-stock
  
  98-80-6
- ~%
- In-stock
  
  142137-17-5
References
- US2003/4153 A1, ;
Route3
- In-stock
  
  625-92-3
- In-stock
  
  591-50-4
- ~50%
- In-stock
  
  142137-17-5
References
- Bonnet, Veronique; Mongin, Florence; Trecourt, Francois; Breton, Gilles; Marsais, Francis; Knochel, Paul; Queguiner, Guy Synlett, 2002 , # 6 p. 1008 - 1010

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

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 Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Phenylpyridines

Key Words

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3-Bromo-5-phenylpyridine

CAS No. 142137-17-5

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