943861-95-8

Basic information

• Product Name: 2,9-dibromo-1,10-phenanthroline-5,6-dione
• Synonyms: 2,9-dibromo-1,10-phenanthroline-5,6-dione
• CAS NO: 943861-95-8
• Molecular Formula: C₁₂H₄Br₂N₂O₂
• Molecular Weight: 367.98036
• Mol File: 943861-95-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 574.3±50.0 °C(Predicted)
• Appearance: /
• Density: 2.068±0.06 g/cm3(Predicted)
• PKA: -4.68±0.20(Predicted)
• CAS DataBase Reference: 2,9-dibromo-1,10-phenanthroline-5,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,9-dibromo-1,10-phenanthroline-5,6-dione(943861-95-8)
• EPA Substance Registry System: 2,9-dibromo-1,10-phenanthroline-5,6-dione(943861-95-8)

Safety Data

• Hazardous Substances Data: 943861-95-8(Hazardous Substances Data)

Usage

General Description

2,9-dibromo-1,10-phenanthroline-5,6-dione is a chemical compound that consists of a phenanthroline ring system with bromine substituents at the 2 and 9 positions, as well as a carbonyl group at the 5,6 positions. It is a derivative of phenanthroline and is commonly used as a ligand in coordination chemistry and as a reagent in organic synthesis. 2,9-dibromo-1,10-phenanthroline-5,6-dione has been studied for its potential biological applications, including its ability to inhibit certain enzymes and its potential as an anti-cancer agent. It also has potential uses in the development of new materials and in the field of fluorescence sensing.

Upstream product

• 39069-02-8 2,9-dibromo-1,10-phenanthroline 
• 66-71-7 1,10-Phenanthroline 
• 39588-59-5 3,6,7,9-tetrahydro-5H-<1,4>diazepino<1,2,3,4-lmn><1,10>phenanthroline-3,9-dione 
• 15302-99-5 6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide 

Downstream Products

• 1245902-40-2 2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione 
• 1245902-39-9 2,9-bis(4-butylphenyl)-1,10-phenanthroline-5,6-dione 
• 1520015-41-1 3,6-dibromo-4,5-diazafluoren-9-one 
• 1415100-76-3 2,9-bis[4-(diphenylamino)phenyl]-1,10-phenanthroline-5,6-dione 

Relevant articles and documents

Highly Ordered, Self-Assembled Monolayers of a Spin-Crossover Complex with In-Plane Interactions

For the technological integration of molecular switches in electronic devices, self-assembling nanomaterials of such switches are highly sought after. The syntheses of a new tetrapyridyl ligand bearing a C12 alkyl chain and two N?H bridges (compound 1) and of its iron(II) complex [Fe(1)(NCS)2] (compound 2), are described. Magnetic susceptibility data for bulk samples of 2 confirmed their gradual spin-crossover properties. The self-assembly of 1 and 2 on highly ordered pyrolytic graphite surfaces (HOPG) was investigated by Scanning Tunneling Microscopy (STM). Both compounds 1 and 2 formed ordered monolayers after deposition by drop casting. The patterns of the two compounds are very different, which is attributed to the fundamentally different hydrogen bonding networks before and after coordination of Fe(NCS)2 to the tetradentate chelate. Two possible models for the self-assembly of 1 and 2 are provided. This work suggests that it is possible to design molecular switches that self-assemble on surfaces in highly ordered monolayer films. This is a significant step in the development of spin-switching materials, which may streamline the integration of molecular switches in for example memory and sensing devices.

Oxidation for unsymmetrical bromo-1,10-phenanthrolines and subsequent hydroxylation, decarbonylation and chlorination reactions

A systematic investigation on the oxidation of unsymmetric bromo-phens is presented herein, where the reaction temperature is found to be the key parameter to generate oxidation or oxidation-bromination products. The regioselective C3-brominated compounds are produced in moderate yields in the cases of 2-bromo-phen and 4-bromo-phen. Subsequent hydroxylation and decarbonylation for bromo-phds are also studied, where a series of bromo-diazafluorenones and phen-triones have been isolated. Furthermore, various chlorination products have been obtained by treating bromo-phds or bromo-phts with excess POCl3.