3,8-Dibromo-1,10-phenanthroline-5,6-dione

Name: 3,8-Dibromo-1,10-phenanthroline-5,6-dione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 602331-25-9
Cat. No. CS-0044193
Purity≥95%
MDL No.None

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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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3,8-Dibromo-1,10-phenanthroline-5,6-dione|CS-0044193

Structure of 602331-25-9

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General Information

CAS No. 602331-25-9
Cat. No. CS-0044193
Purity ≥95%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₄Br₂N₂O₂
Molecular Weight 367.98
Synonym(s) 1,10-Phenanthroline-5,6-dione,3,8-dibromo
SMILES O=C1C2=C(C3=C(C1=O)C=C(C=N3)Br)N=CC(Br)=C2

Description

3,8-Dibromo-1,10-phenanthroline-5,6-dione features two bromine substituents at the 3 and 8 positions of the phenanthroline core, enhancing electron-withdrawing character and facilitating metal coordination. The quinone functionality at the 5,6-positions enables redox activity and integration into coordination complexes. This compound serves as a robust ligand in transition metal chemistry, particularly for copper and nickel systems, offering improved stability and tailored electronic properties under standard conditions.

Application

3,8-Dibromo-1,10-phenanthroline-5,6-dione serves as a versatile chelating ligand scaffold for transition metal catalysis, offering enhanced electronic modulation through bromine substitution. Its ortho-quinone functionality enables reliable coordination to metals such as Cu(I) and Ni(II), facilitating applications in cross-coupling reactions and complex heterocycle synthesis. The compound exhibits good bench stability and facilitates purification via recrystallization, making it well-suited for iterative synthetic workflows in medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  100125-12-0
- ~91%
- In-stock
  
  602331-25-9
References
- Yamamoto, Takakazu; Anzai, Kazushige; Fukumoto, Hiroki Chemistry Letters, 2002 , # 8 p. 774 - 775

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

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Computational Chemistry Data

TPSA 59.92
LogP 3.0476
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Catalysts and Ligands Ligands Pyridine Ligands Phenanthroline Ligands

Catalysis Nitrogen-Donor Ligands Pyridine Ligands

Catalysis Nitrogen-Donor Ligands Phenanthroline Ligands

Material Science Material Building Blocks Covalent Organic Frameworks (COFs) Linkers Linkers (Others)

Material Science Polymer/Macromolecule Reagents Covalent Organic Frameworks (COFs) Linkers Linkers (Others)

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3,8-Dibromo-1,10-phenanthroline-5,6-dione

CAS No. 602331-25-9

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