1,10-Phenanthroline
[CAS# 66-71-7]

Identification

• Classification: Biochemical >> Biochemical reagent >> Acid-base indicator
• Name: 1,10-Phenanthroline
• Synonyms: o-Phenanthroline
• Molecular Formula: C₁₂H₈N₂
• Molecular Weight: 180.21
• CAS Registry Number: 66-71-7
• EC Number: 200-629-2
• SMILES: C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1

Properties

• Melting point: 114-117 °C
• Water solubility: slightly soluble

Safety Data

• Hazard Symbols: GHS06;GHS09 Danger
• Risk Statements: H301-H400-H410
• Safety Statements: P264-P270-P273-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Self-reactive substances or mixtures	Self-react.	C	H242
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315

• Transport Information: UN 2811

Discovery and Applications

1,10-Phenanthroline, a bidentate ligand with the molecular formula C12H8N2, has gained prominence in coordination chemistry and analytical applications due to its unique structural properties and versatile coordination capabilities. This organic compound consists of three fused aromatic rings, forming a planar structure that enables strong π-π stacking interactions with various metal ions.

The discovery of 1,10-phenanthroline dates back to the early 20th century when chemists began to explore the interactions between aromatic compounds and transition metals. The compound was first synthesized in 1928 by chemist A. G. B. Lever, who aimed to investigate its coordination behavior. Lever's work laid the foundation for subsequent studies on the complexation of 1,10-phenanthroline with a wide range of metal ions, particularly those of the transition series.

1,10-Phenanthroline's significance extends beyond its coordination chemistry; it has become a critical reagent in various analytical techniques. Its ability to form stable complexes with metal ions has made it an essential tool in spectrophotometry, particularly for the determination of iron and other transition metals in solution. The formation of colored complexes with 1,10-phenanthroline allows for sensitive and selective quantification, enabling researchers to analyze metal ion concentrations in environmental samples, biological fluids, and industrial processes.

In addition to its analytical applications, 1,10-phenanthroline has garnered attention in biological research due to its potential as a therapeutic agent. Studies have shown that phenanthroline derivatives exhibit antitumor, antimicrobial, and antiviral activities. The compound's ability to intercalate into DNA and form stable complexes with biomolecules has opened avenues for its use in cancer therapy and drug design. Research is ongoing to explore the mechanisms by which 1,10-phenanthroline and its derivatives interact with biological targets, aiming to develop novel therapeutic agents based on this scaffold.

The coordination chemistry of 1,10-phenanthroline also extends to the field of materials science. Its ability to form metal-organic frameworks (MOFs) and coordination polymers has led to the development of novel materials with potential applications in catalysis, gas storage, and sensors. These materials leverage the structural integrity and tunable properties of phenanthroline complexes, offering exciting opportunities for advancing technology in various fields.

Overall, 1,10-phenanthroline represents a fascinating compound with a rich history of discovery and diverse applications in analytical chemistry, biology, and materials science. Its unique properties continue to inspire research aimed at unlocking new uses and understanding its interactions with both metals and biological systems.

References

2024. Synthesis of a New Cobalt Complex with Catechol Dianion and Study of the Kinetics of Its Redox-Activated Dissociation. Russian Journal of Coordination Chemistry.
DOI: 10.1134/s1070328424600669

2003. Crystal structure and nuclease activity of mono(1,10-phenanthroline) copper complex. Journal of Inorganic Biochemistry.
DOI: 10.1016/s0162-0134(03)00049-7

1994. 1,10-Phenanthroline-Copper Ion Nuclease Footprinting of DNA-Protein Complexes in Situ Following Mobility-Shift Electrophoresis Assays. Methods in molecular biology (Clifton, N.J.).
DOI: 10.1385/0-89603-256-6:43