3922-40-5

Usage

Uses

Used in Analytical Chemistry:
4,7-Dihydroxy-1,10-phenanthroline is used as a reagent for the spectrophotometric determination of dissolved oxygen in aqueous solutions. Its iron(II) complex reacts rapidly with dissolved oxygen, making it a valuable tool for measuring oxygen concentrations up to 20 ppm. This application is particularly useful in environmental monitoring, water treatment, and industrial processes where accurate oxygen level measurements are crucial.

InChI:InChI=1/C12H8N2O2/c15-9-3-5-13-11-7(9)1-2-8-10(16)4-6-14-12(8)11/h1-6H,(H,13,15)(H,14,16)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 503863-91-0 1,2-bis-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)amino]benzene 

Downstream Products

• 111301-95-2 4,7-bis(benzyloxy)-1,10-phenanthroline 
• 111301-94-1 1-Benzyl-7-benzyloxy-1H-[1,10]phenanthrolin-4-one 
• 5394-23-0 4,7-dichloro-1,10-phenanthroline 
• 156492-30-7 4,7-dibromo-1,10-phenanthroline 
• 92149-07-0 4,7-dimethoxy-1,10-phenanthroline 
• 359820-25-0 4-[(3-benzyloxy-4-nitro)phenoxy]-7-hydroxy-1,10-phenanthroline 
• 359820-24-9 4,7-bis[(3-benzyloxy-4-nitro)phenoxy]-1,10-phenanthroline 
• 192226-55-4 4,7-bis(phenylethinyl)-1,10-phenanthroline 

Relevant academic research and scientific papers

Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles

In the presence of carbon monoxide, the palladium/phenanthroline system catalyzes the intramolecular amination of thiophene rings following the reduction of a nitroalkene moiety directly attached to the S-heterocyclic ring. Optimization of the ligand and reaction conditions allowed the synthesis of a series of thienopyrroles aryl/alkyl-substituted at either the 2- or 3-position of the pyrrole ring. By using low pressures of carbon monoxide (5 bars), high yields of fused bicyclic compounds have been obtained (up to 98 % yield).

Copper-catalyzed N-arylation of imidazoles and benzimidazoles

(Chemical Equation Presented) 4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.

4,7-Dimethoxy-1,10-phenanthroline: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles

4,7-Dimethoxy-1,10-phenanthroline (L) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazole with aryl iodides and bromides under mild conditions. A variety of hindered and functionalized imidazoles and aryl halides were transformed in good to excellent yields.

Production method of a cross-coupling compound from an alkyl halide and an organoboron compound

There is provided a method for producing a coupling compound of formula (1):(Y-)(n-1)R1-R2-(R1)(n'-1) wherein R1, R2 n and n' are as defined below, Y is R2 or X as defined below, which method comprises reactinganorganichalogen compound of formula (2):n' (R1X1n) wherein X1 represents a bromine or iodine, R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X1 are sp3 carbon atoms, n and n' each independently represent an integer of 1 or 2, and provided that n and n' do not simultaneously represent 2, with an organic boron compound of formula (3):m{R2(BX22)n'} wherein R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group and the boron atom is bonded with an sp2 carbon atom thereof, X2 represents a hydroxyl or alkoxy group, n' is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, and ???b) b-1) a compound of formula (i): ???or ???b-2) a compound of formula (ii):