148231-12-3

Basic information

• Product Name: 5,8-DibroMoquinoxaline
• Synonyms: 5,8-DibroMoquinoxaline;Quinoxaline, 5,8-dibroMo-;5,8-Dibromoquinoxaline 97%
• CAS NO: 148231-12-3
• Molecular Formula: C₈H₄Br₂N₂
• Molecular Weight: 287.93876
• Mol File: 148231-12-3.mol

Chemical Properties

• Melting Point: 198-203°C (dec.)
• Boiling Point: 352.5±37.0 °C(Predicted)
• Appearance: /
• Density: 2.022±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.28±0.30(Predicted)
• CAS DataBase Reference: 5,8-DibroMoquinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-DibroMoquinoxaline(148231-12-3)
• EPA Substance Registry System: 5,8-DibroMoquinoxaline(148231-12-3)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-39-45
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 148231-12-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,8-Dibromoquinoxaline is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of complex nitrogen-containing molecules, which are essential in the synthesis of new drugs and therapeutic agents.
Used in Chemical Research:
5,8-Dibromoquinoxaline is used as a research compound in the field of organic chemistry. Its reactivity and ability to form various nitrogen-containing molecules make it a valuable tool for studying chemical reactions and mechanisms.
Used in Material Science:
5,8-Dibromoquinoxaline is used as a building block in the synthesis of advanced materials, such as organic semiconductors and conducting polymers. Its incorporation into these materials can lead to improved properties, such as enhanced conductivity and stability.
Used in Agrochemical Industry:
5,8-Dibromoquinoxaline is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in forming nitrogen-containing molecules can contribute to the development of more effective and environmentally friendly agrochemical products.
Used in Dye and Pigment Industry:
5,8-Dibromoquinoxaline is used as a starting material in the production of dyes and pigments. Its ability to form complex molecules can lead to the creation of new colors and improved properties, such as lightfastness and stability.

Upstream product

• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 131543-46-9 Glyoxal 
• 1241375-11-0 3,6-dibromocyclohexa-3,5-diene-1,2-diamine 
• 95-54-5 1,2-diamino-benzene 
• 3476-89-9 1,2,3,4-tetrahydroquinoxaline 
• 2423-66-7 quinoxaline 1,4-di-N-oxide 
• 91-19-0 2,3-diethynylquinoxaline 
• 528852-07-5 (R,S)-5-bromo-5,6,7,8-tetrahydroquinoxaline 
• 34413-35-9 5,6,7,8-tetrahydroquinoxaline 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 69272-50-0 1,2-diamine-3,6-dibromobenzene 

Downstream Products

• 705973-29-1 N,N'-diphenyl-quinoxaline-5,8-diamine 
• 1197331-91-1 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile 
• 1197332-50-5 5-bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline 
• 1197331-90-0 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid 
• 1197332-94-7 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester 
• 1197332-49-2 8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile 
• 1197332-47-0 5-bromo-8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline 
• 1197332-48-1 8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid 
• 1197333-25-7 8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester 
• 1197332-45-8 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile 

Relevant articles and documents

Synthesis, Properties, and Reactivity of Bis-BN Phenanthrenes: Stepwise Bromination of the Main Scaffold

Two bis-BN phenanthrenes have been synthesized. Their photophysical properties are different from those of the reported mono-BN phenanthrenes. Moreover, the stepwise bromination of bis-BN phenanthrene 8 gave a series of brominated bis-BN phenanthrenes, wi

Molecular 5,8-π-extended quinoxaline derivatives as chromophores for photoluminescence applications

The 5,8-π-extended quinoxaline derivatives are widely studied due to their well-known photophysical and electrochemical properties. In order to investigate the structure-property relationship, a novel series of fluorescent calamitic liquid crystals based on the quinoxaline heterocycle was successfully synthesized and characterized. The final molecules presented calamitic mesomorphism with nematic and smectic phases. These compounds displayed intense green photoluminescence under UV light excitation in solution and in the solid state. In chloroform solution, the fluorescence quantum yields (ΦFL = 0.54–0.62) of the quinoxaline-based derivatives were significantly higher than those previously described for similar benzothiadiazoles. The maximum emission peaks were between 511 and 520 nm with singlet excited-state lifetimes in the nanosecond timescale. The solvatochromism studies showed a significant dependence of the emission on the polarity of the solvent. Doping of the quinoxalines with fullerene C60 suggests a charge transfer process, this being dependent on the π-conjugate core. The energy band gaps predicted with DFT calculations are in excellent agreement with the experimental data.

Are molecular 5,8-π-extended quinoxaline derivatives good chromophores for photoluminescence applications?

The synthesis of a new series of photoluminescent compounds, namely 5,8-diaryl quinoxaline derivatives (aryl = phenyl, 4-fluorophenyl, 4-methoxyphenyl, and 4-cyanophenyl), was achieved by a direct Suzuki cross-coupling reaction with the employment of a NCP-pincer palladacycle. The electrochemical and photophysical properties of these compounds were also investigated. Four new 4,8-diaryl-2,1,3-benzothiadiazoles were also synthesized in order to enable a comparison between the two types of nitrogen-containing π-extended heterocycles. The substitution of a hydrogen atom at the 4-position of the aryl that is groups attached to the quinoxaline or benzothiadiazole base by either electron-donating or -withdrawing groups results in an increase in the bandgap energy (from 2.21 to 2.52 eV) of π-extended 5,8-quinoxaline derivatives and a decrease in the bandgap energy (from 2.65 to 2.40 eV) of π-extended 2,1,3-benzothiadiazoles. Moreover, π-extension at the 5- and 8-positions of the quinoxaline core is not essential for the photoluminescence of these compounds and 4,7-π-extended 2,1,3- benzothiadiazole derivatives are far better candidates for luminescence applications than are the quinoxaline derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

New quinoxaline derivatives as accepting units in donor-acceptor type low-band gap polymers for organic photovoltaic cells

A series of new donor-acceptor-type low-band-gap semiconducting polymers were synthesized as electron donors for organic photovoltaic cells. The polymers comprised quinoxaline derivatives as the acceptors and a benzodithiophene (BDT) derivative as the don

Preparation of new electron-accepting π-conjugated polyquinoxalines. Chemical and electrochemical reduction, electrically conducting properties, and use in light-emitting diodes

Dehalogenation polycondensation of 5,8-dibromoquinoxaline derivatives and 2,6-dibromoquinoxaline with zerovalent nickel complex affords a series of π-conjugated polyquinoxalines with a molecular weight of 6 x 103 to 260 x 103. The polymers are electrochemically reduced (or n-doped) with an E° value of -1.75 to -2.35 V vs Ag/Ag+ and converted into electrically conducting materials with a conductivity of 1 x 10-4 to 7 x 10-3 S cm-1 by chemical reduction. Poly(quinoxaline-5,8-diyl)s with aromatic substituents give strong fluorescence with emission peaks at 450-520 nm in solutions as well as in cast films. A light-emitting diode (LED), ITO/polymer/Mg(Ag) (polymer = poly(2,3-diphenylquinoxaline-5,8-diyl)), emits blue-green light (λ(max) at about 500 nm). Introduction of hole-transporting layers such as vacuum-deposited or spin-coated thin layers of poly(thiophene-2,5-diyl), poly(p-phenylene), and poly(N-vinylcarbazole) between ITO and the light-emitting layer enhances electroluminescence efficiency by about 2 orders of magnitude. Polyquinoxalines have an ionization potential of 5.83 ± 0.11 eV and a band gap of 2.56 ± 0.26 eV.

Synthesis, characterization and properties of aryl-fused bis-BN dihydropyrenes

A series of aryl-fused bis-BN dihydropyrenes were synthesized via amino-directed borylation reaction. The aryl-fused bis-BN dihydropyrenes showed blue emission, and their physical properties could be finely tuned through varying the fused aryl rings. In particular, their response towards fluoride anions was greatly dependent on the nature of the fused aryl rings.

Bromination of quinoxaline and derivatives: Effective synthesis of some new brominated quinoxalines

The synthesis of brominated quinoxaline derivatives starting from several kinds of quinoxaline by different bromination strategies was studied. First the synthesis of some brominated quinoxalines was accomplished along with the development of an alternative and effective synthesis of some known compounds. A new, clean, and effective synthetic method for selective reduction of quinoxaline to 1,2,3,4-tetrahydroquinoxaline was also developed. The products obtained were characterized by means of NMR spectroscopy, elemental analyses, and mass spectrometry.

Benzodipyrrole-based Donor–Acceptor-type Boron Complexes as Tunable Near-infrared-Absorbing Materials

Benzodipyrrole-based donor–acceptor boron complexes were designed and synthesized as near-infrared-absorbing materials. The electron-rich organic framework combined with the Lewis acidic boron co-ordination enabled us to tune the LUMO energy level and the HOMO–LUMO gap (i.e.,the absorption wavelength) by changing the organic acceptor units, the number of boron atoms, and the substituents on the boron atoms.

D-A-π-A featured sensitizers by modification of auxiliary acceptor for preventing "trade-off" effect

Four D-A-π-A motif organic sensitizers (IQ9, IQ10, IQ11 and IQ12) in the absence or presence of thiophene substituents grafted onto the auxiliary acceptor of a quinoxaline unit have been developed for dye sensitized solar cells (DSSCs). Upon changing the

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