4199-89-7

Usage

Uses

Used in Chemical Synthesis:
5-Chloro-1,10-phenanthroline is used as a precursor in the preparation of 1,10-phenanthrolinium cation, a versatile intermediate for the synthesis of a wide range of chemical compounds. Its unique structure allows for the formation of various derivatives with diverse applications.
Used in the Design of Ionic Liquid Crystals:
In the field of materials science, 5-chloro-1,10-phenanthroline is utilized as a new building block for the design of ionic liquid crystals. These liquid crystals exhibit unique properties, such as self-assembly and responsiveness to external stimuli, making them suitable for various applications, including display technologies and sensors.
Used in the Preparation of Platinum(II)-based Metallointercalators:
5-Chloro-1,10-phenanthroline is also employed in the synthesis of platinum(II)-based metallointercalators, which are compounds that can bind and interact with DNA. These metallointercalators have potential applications in the development of new drugs for the treatment of various diseases, including cancer, by targeting specific DNA sequences and disrupting their function.

InChI:InChI=1/C12H7ClN2/c13-10-7-8-3-1-5-14-11(8)12-9(10)4-2-6-15-12/h1-7H

Upstream product

• 5470-75-7 8-amino-6-chloroquinoline 
• 56-81-5 glycerol 
• 607-35-2 8-nitroquinoline 
• 7647-01-0 hydrogenchloride 
• 366-18-7 [2,2]bipyridinyl 
• 68527-66-2 6-chloro-8-nitroquinoline 
• 89-63-4 4-Chloro-2-nitroaniline 
• 66-71-7 1,10-Phenanthroline 

Downstream Products

• 366-18-7 [2,2]bipyridinyl 
• 96761-79-4 5,5'-bi-1,10-phenanthroline 
• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 144204-69-3 {Cu(5-chloro-1,10-phenanthroline)(phenylacetylene)}⁽¹⁺⁾ 
• 105083-36-1 Cu(C₁₂H₇N₂(Cl))(P(C₆H₅)3)2⁽¹⁺⁾*BF₄^(1-)=(Cu(C₁₂H₇N₂(Cl))(P(C₆H₅)3)2)BF₄ 
• 230953-51-2 (VO)2(Br₂C₆O₄)(C₁₂H₇ClN₂)2⁽²⁺⁾*SO₄^(2-)=[(VO)2(Br₂C₆O₄)(C₁₂H₇ClN₂)2](SO₄) 
• 7664-93-9 sulfuric acid 
• 1421675-24-2 2-phenyl-5-(2-(piperidin-1-yl)ethyloxy)-1,10-phenanthroline 

Relevant academic research and scientific papers

Is the formation of 1,10-phenanthroline di-N-oxide possible?

5,6-Dichloro-5,6-dihydro-1,10-phenanthroline (2) was found as an additional product of the hypochlorous acid action on 1,10-phenanthroline. When treated with MCPBA the product of the chlorine addition yielded a corresponding di-N-oxide 3, which readily lost hydrogen chloride under the influence of sodium isopropoxide. The resulting monochloro di-N-oxide 5 molecules (assumed to be flat) revealed a satisfactory stability unless the neutral or basic solution was made acidic.

Thermodynamic studies of the binding of bidentate nitrogen donors with methyltrioxorhenium (MTO) in CHCl3 solution

Methyltrioxorhenium (MTO) adduct formation with bidentate nitrogen donors 2,2′-bipyridine (bpy), 4,4′-dimethyl-2,2′-bipyridine (Me 2bpy), 4,4′-di-tert-butyl-2,2′-bipyridine ( tBu2bpy), 1,10-phenanthroline (phen), 5-methyl-

On the chlorine addition to the C(5)-C(6) bridge and the N-oxidation of 1,10-phenanthroline

It was found that under the influence of aqueous hypochlorite 1,10-phenanthroline (1) is initially transformed into 5,6-dichloro-5,6-dihydro-1,10-phenanthroline (2) and 5-chloro-6-hydroxy-5,6-dihydro-1,10-phenanthroline (8). The latter readily undergoes subsequent transformations either into a mixture of 5,5-dichloro-6-oxo-5,6-dihydro-1,10-phenanthroline (4) and 5,6-dioxo-5,6-dihydro-1,10-phenanthroline (5) or into the known 5,6-epoxy-1,10-phenanthroline (3) depending on the acidic or alkaline conditions, respectively. In contrast to the flat molecule of the starting 1, that of the dichloro derivative (2) being twisted at the central bond of the bipyridine system can be easily N-oxidized to di-N-oxide (11). Both 2 and its di-N-oxide (11) in the presence of sodium isopropoxide at 0°C freely lost hydrogen chloride and returned to the fully aromatic system of 5-chloro-1,10-phenanthroline (9) and its di-N-oxide (13), respectively.

Electron Transfer and Ion Pairing, 27. Preparation of Semiquinone Ion Pairs by Reduction of Quinones Using Tetraalkylammonium Boranate in Aprotic Salt Solutions: 1,10-Phenanthrolin-5,6-dione

Ion pairs of 1,10-phenanthrolin-5,6-dione radical anion -Me+n>*+(n-1) with Me+n = Mg2+, Ca2+, Sr2+, Zn2+, Cd2+, Pb2+ and La3+ are advantageously prepared in aprotic DMF solution containing appropriate metal salts Me+nX- by using the "mild" single-electron reducing agent tetra(n-butyl)ammonium-boranate R4N+BH4-.For comparison, the "nacked" radical anion with the largely interaction-free + counter cation is chosen, which is formed on reduction with potassium in THF solution of (2.2.2)-cryptand.Addition of excess Na+- to the reduction solution only yields a solvent-separated ion pair M*-)DMF...(Na+)DMF, whereas in the presence of multiply charged counter cations Me+n the respective contact ion pair radical cations -Me+n>*+(n-1) are formed.Their g values decrease with increasing nuclear charge of Me+n and their metal-s-spin densities increase with the effective counter cation charge n+/rMe+n.The ESR/ENDOR data recorded suggest Me+n complexation by the δ-OC-COδ- chelate tongs and the ion pair stability, which is modified by the dielectric properties of the solvent used, may be rationalized by the Coulombic attraction between the radical anion M*- and the counter cations Me+n.Keywords: 1,10-Phenanthrolin-5,6-dione, Reduction by R4N+BH4-, Contact Ion Pairs, ESR/ENDOR Spectra

Catalyst compositions and a process for polymerizing carbon monoxide and olefins

Carbon monoxide and at least one olefinically unsaturated organic compound may be polymerized by contacting the monomers in the presence of a catalyst which comprises a Group VIII metal compound of palladium, cobalt or nickel, a halide of tin or germanium, a nitrogen bidentate ligand and an organic oxidant. The polymers prepared are linear alternating polymers which consist of units with the formula STR1 where A is the residue of an alkenically unsaturated organic compound monomer.