5-Nitro-1,10-phenanthroline

Name: 5-Nitro-1,10-phenanthroline
Brand: ChemScene
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CAS No. 4199-88-6
Cat. No. CS-W004570
Molecule weightNone
Purity≥97%
MDL No.MFCD00004981

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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 4199-88-6

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General Information

CAS No. 4199-88-6
Cat. No. CS-W004570
Purity ≥97%
MDL No. MFCD00004981
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₇N₃O₂
Molecular Weight None
Synonym(s) 5-NP
SMILES O=[N+]([O-])C1=C2C(N=CC=C2)=C3C(C=CC=N3)=C1

Description

5-Nitro-1,10-phenanthroline is a bench-stable, electron-deficient chelator featuring a para-nitro group that enhances metal-binding affinity. This rigid, planar ligand integrates readily into coordination complexes and serves as a robust scaffold for catalytic systems requiring tunable redox properties.

Application

5-Nitro-1,10-phenanthroline serves as a versatile bidentate ligand in transition metal catalysis, particularly in palladium- and copper-mediated coupling reactions. Its electron-deficient aromatic system enhances metal coordination strength, while the nitro group provides tunable electronic modulation. The compound exhibits good bench stability and facilitates efficient complex formation, enabling reliable performance in cross-coupling and cyclization processes.

Synthesis

Route1
- In-stock
  
  66-71-7
- ~98%
- In-stock
  
  4199-88-6
References
- Ji, Shaomin; Guo, Huimin; Yuan, Xiaolin; Li, Xiaohuan; Ding, Haidong; Gao, Peng; Zhao, Chunxia; Wu, Wenting; Wu, Wanhua; Zhao, Jianzhang Organic Letters, 2010 , vol. 12, # 12 p. 2876 - 2879
Route2
- 5144-89-8
- ~42%
- In-stock
  
  4199-88-6
References
- Nisshinbo Industries, Inc. Patent: US5856479 A1, 1999 ;
Route3
- In-stock
  
  66-71-7
- ~0%
- In-stock
  
  27318-90-7
- In-stock
  
  4199-88-6
References
- Amouyal, Edmond; Homsi, Abdulrazzak; Chambron, Jean-Claude; Sauvage, Jean-Pierre Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1990 , # 6 p. 1841 - 1845

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 68.92
LogP 2.6912
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Natural Products

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

Analytical Chemistry Analytical Reagents Titration Reagents Indicators for Titration

Key Words

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5-Nitro-1,10-phenanthroline

CAS No. 4199-88-6

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