3-Bromo-1,10-phenanthroline

CAS No. 66127-01-3
Cat. No. CS-W004585
Molecule weight259.10
Purity≥98%
MDL No.MFCD08276287

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Structure of 66127-01-3

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General Information

CAS No. 66127-01-3
Cat. No. CS-W004585
Purity ≥98%
MDL No. MFCD08276287
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₇BrN₂
Molecular Weight 259.10
Synonym(s) 3-BROMO-1,10-PHENTHROLINE
SMILES BrC1=CC2=CC=C(C=CC=N3)C3=C2N=C1

Description

3-Bromo-1,10-phenanthroline is a bench-stable, electron-deficient heteroaromatic ligand featuring a bromine substituent at the 3-position. This substitution enhances its utility in transition metal catalysis and coordination chemistry, enabling efficient coupling reactions and stable complex formation. The rigid planar structure facilitates π-stacking interactions and promotes predictable binding geometry in metal complexes.

Application

3-Bromo-1,10-phenanthroline serves as a versatile ligand scaffold in transition metal catalysis, enabling palladium- and copper-catalyzed cross-coupling reactions. Its bromine substituent facilitates further functionalization via standard coupling protocols, while the rigid aromatic framework provides strong metal chelation. The compound exhibits excellent bench stability and ease of purification, making it suitable for iterative synthesis and catalyst development in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  3829-86-5
- ~33%
- In-stock
  
  66127-01-3
- In-stock
  
  100125-12-0
References
- Tetrahedron Letters, , vol. 36, # 20 p. 3489 - 3490
Route2
- In-stock
  
  3829-86-5
- ~25%
- In-stock
  
  66127-01-3
References
- Laurent, Alain; Wright, Michael; Laayoun, Ali; Meunier, Bernard; Tissot, Ludivine; Pitie, Marguerite Nucleosides, Nucleotides and Nucleic Acids, 2007 , vol. 26, # 8-9 p. 927 - 930
Route3
- In-stock
  
  66-71-7
- ~38%
- In-stock
  
  66127-01-3
- In-stock
  
  100125-12-0
References
- Journal of Materials Chemistry, , vol. 11, # 7 p. 1769 - 1771

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 25.78
LogP 3.5455
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Catalysts and Ligands Ligands Pyridine Ligands Phenanthroline Ligands

Material Science Material Building Blocks Ligands for Functional Metal Complexes Phenanthroline Ligands

Catalysis Nitrogen-Donor Ligands Pyridine Ligands

Catalysis Nitrogen-Donor Ligands Phenanthroline Ligands

Key Words

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3-Bromo-1,10-phenanthroline

CAS No. 66127-01-3

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