3331-28-0

Basic information

• Product Name: Phenazine, 2-broMo-
• Synonyms: Phenazine, 2-broMo-
• CAS NO: 3331-28-0
• Molecular Formula: C₁₂H₇BrN₂
• Molecular Weight: 259.10138
• EINECS: -0
• Mol File: 3331-28-0.mol

Chemical Properties

• Melting Point: 150℃
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Phenazine, 2-broMo-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenazine, 2-broMo-(3331-28-0)
• EPA Substance Registry System: Phenazine, 2-broMo-(3331-28-0)

Safety Data

• Hazardous Substances Data: 3331-28-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenazine, 2-bromo-, is used as a key intermediate in the synthesis of new pharmaceuticals. Its unique chemical properties and potential biological activities make it a valuable building block for the development of novel drugs with improved therapeutic effects.
Used in Antimicrobial Applications:
Phenazine, 2-bromo-, is used as an antimicrobial agent due to its ability to inhibit the growth of various microorganisms. Its bromine atom may enhance its antimicrobial activity, making it a potential candidate for the development of new antimicrobial drugs or as a component in existing formulations.
Used in Anticancer Applications:
Phenazine, 2-bromo-, is used as an anticancer agent due to its potential to exhibit antitumor properties. Its unique chemical structure and bromine atom may contribute to its ability to target and inhibit the growth of cancer cells, making it a promising candidate for further research and development in cancer therapy.
Used in Chemical Research:
Phenazine, 2-bromo-, is used as a subject of interest in chemical research for its unique properties and potential applications. Researchers are exploring its potential uses in the development of new chemical compounds with specific biological activities, as well as its role in drug discovery and development.

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Relevant articles and documents

Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

The mixed-valence character of four bis(N,N-dihydrodimethylphenazine) radical cation derivatives with varying π-electron bridges was investigated. The electron transfer (ET) distance within these derivatives varies from ca. 12.5 A? for 1,2-bis[2-(5,10-dihydro-5,10-dimethylphenazinyl)]acetylene (1) to ca. 19.3 A? for 9,10-bis[2-(5,10-dihydro-5,10-dimethylphenazinyl)ethynyl]anthracene (4). All radical cation species show intense intervalence charge-transfer (IV-CT) bands in the NIR. The Mulliken-Hush analysis was used to derive the electronic coupling V, which ranges from 310 to 870 cm-1. Comparisons with analogous ET systems in which the dihydrodimethylphenazine redox centres have been replaced by triarylamine units show that the dihydrodimethylphenazine species have a significantly higher internal reorganisation energy associated with the ET. This behaviour is attributed to C-N stretching and C-C ring modes of the dihydrodimethylphenazine units.

Synthesis of Cyclobutadienoid-Fused Phenazines with Strongly Modulated Degrees of Antiaromaticity

The streamlined synthesis of a series of regioisomeric azaacene analogues containing fused phenazine and antiaromatic cyclobutadienoids (CBDs), using a catalytic arene-oxanorbornene annulation, followed by aromatization is reported. Controlling the fusion patterns allowed strong modulation of local antiaromaticity. Enhancing antiaromaticity in these regioisomeric azaacenes led to stabilized LUMO, reduced band gap, and quenched fluorescence. This synthetic strategy provides a facile means to fuse CBDs with variable degrees of antiaromaticity onto N-heteroarenes to tune their optoelectronic properties.

The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines

A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.

An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine

Herein, Ag(I)-promoted regioselective intramolecular radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence (TADF) materials based on phenazine exhibit emission bands from green to red with high quantum yields and moderate fluorescence lifetimes as solid films.

Preparation method of phenazine compound

To the method, a phenazine compound is prepared through continuous ortho C-H functionalization, nitroso insertion and decarboxylation processes of aryl carbamic acid, wherein a carboxyl amino group serves as a trace-free positioning group.

A polysubstituted phenazine derivative and its oxide high-efficient preparation method (by machine translation)

The invention belongs to the technical field of chemical preparation of a polysubstituted phenazine derivative and its oxide high-efficient preparation method. The preparation method is added to the reactor in the diaryl expensive Iodized salt, benzo furazane, copper-based catalyst, replacing nitrogen after three times, adding solvent, finishing feeding the heating reaction; the end of the reaction, after cooling to room temperature after treatment, separating, purifying to obtain the phenazine oxide pure product; phenazine oxide product can be further reduction, after treatment, separation, purification phenazine derivatives. The present invention provides a multi-substituted phenazine derivative and its oxide process is reasonable, can be synthesized by other method is difficult to synthesis of the asymmetric multi-substituted phenazine derivatives, the preparation method is simple, high yield, the product is easy to purification. (by machine translation)

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

A phenazine group substituted polycyclic aromatic hydrocarbon derivatives and use thereof (by machine translation)

The invention relates to a phenazine group substituted polycyclic aromatic hydrocarbon derivatives, such compounds have the formula (1) of the structure shown. The invention phenazine group substituted polycyclic aromatic hydrocarbon derivatives, is suitable for the electric light emitting display made in the ETL material. The use of the material of the present invention, the turn-on voltage of the device can be reduced, thereby improving the luminous efficiency of the device, thereby increasing the service life of the device. (by machine translation)

Hydrobromic acid-dimethyl sulfoxide reagent for dealkylation of 5,10-dialkyl-5,10-dihydrophenazines: Synthesis of 10-alkyl- 2(10H)-phenazinones

By the reaction of 5,10-dialkyl-substituted 5,10- dihydrophenazine with hydrobromic acid in dimethyl sulfoxide at 90-110°, 10-alkyl-2(10H)-phenazinone was obtained as a major product. Brominated dihydrophenazine was isolated in the case of 1,6-dichloro-5,10-dimethyl-5,10-dihydrophenazine.