52431-30-8

Basic information

• Product Name: 2,5-DIBROMO-3,4-DINITROTHIOPHENE
• Synonyms: 2,5-DIBROMO-3,4-DINITROTHIOPHENE;AKOS 92299;2,5-Dibromo-3,4-dinitrthiphene;2,5-DIBROMO-3,4-DINITROTHIOPHENE 98+%;2,5-DibroMo-3,4-dinitrothiophene 98%;NSC 84661;DibroMo-3,4-dinitrothio;2,5-Dibromo-3,4-dinitrothiophene,95%
• CAS NO: 52431-30-8
• Molecular Formula: C₄Br₂N₂O₄S
• Molecular Weight: 331.93
• EINECS: -0
• Product Categories: Thiophenes;Metal Isotopes;Sulfur & Selenium Compounds;Thiophene Series
• Mol File: 52431-30-8.mol

Chemical Properties

• Melting Point: 137°C
• Boiling Point: 341.2°Cat760mmHg
• Flash Point: 160.2°C
• Appearance: /
• Density: 2.459g/cm³
• Vapor Pressure: 0.000161mmHg at 25°C
• Refractive Index: 1.716
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetone, Methanol
• Water Solubility: Insoluble in water.
• BRN: 218219
• CAS DataBase Reference: 2,5-DIBROMO-3,4-DINITROTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBROMO-3,4-DINITROTHIOPHENE(52431-30-8)
• EPA Substance Registry System: 2,5-DIBROMO-3,4-DINITROTHIOPHENE(52431-30-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37
• WGK Germany: 3
• Hazardous Substances Data: 52431-30-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,5-DIBROMO-3,4-DINITROTHIOPHENE is used as a reagent in the synthesis of bromodinitro compounds and polymers. Its application is particularly relevant in the formation of conjugated thiophene oligomers or co-oligomers, which are essential components in the development of advanced materials for various industries.
Used in Pd-Catalyzed Stille Coupling:
In the field of organic chemistry, 2,5-DIBROMO-3,4-DINITROTHIOPHENE is used as a monomer in the Pd (palladium) catalyzed Stille coupling process. This reaction is crucial for creating conjugated thiophene oligomers or co-oligomers, which have potential applications in electronic devices, photovoltaics, and other areas.
Used in Material Science:
2,5-DIBROMO-3,4-DINITROTHIOPHENE is also utilized in material science for the development of novel materials with specific properties. Its role in the synthesis of polymers and thiophene-based materials makes it a valuable component in the advancement of materials with potential applications in various industries, such as electronics, energy, and pharmaceuticals.
Used in Pharmaceutical Applications:
2,5-DIBROMO-3,4-DINITROTHIOPHENE can be used as a starting material for the synthesis of pharmaceutical compounds. The reduction of this compound yields 3,4-diaminothiophene, which can be further utilized in the development of therapeutic agents.

InChI:InChI=1/C4Br2N2O4S/c5-3-1(7(9)10)2(8(11)12)4(6)13-3

Upstream product

• 3141-27-3 2,5-dibromothiophen 
• 3141-24-0 2,3,5-tribromothiophene 
• 188290-36-0 thiophene 

Downstream Products

• 78637-85-1 thiophene-3,4-diamine 
• 69723-91-7 2-bromo-3,4-dinitrothiophene 
• 205170-72-5 3’,4’-dinitro-2,2’:5’,2’’-terthiophene 
• 851233-21-1 4,4'-(3,4-dinitrothiophene-2,5-diyl)bis(N,N-diphenylaniline) 
• 90069-81-1 thiophene-3,4-diamine dihydrochloride 
• 1247952-42-6 C₁₆H₈Br₂N₂O₄S 
• 1190213-32-1 3,4-dinitro-2,5-bis(4-trifluoromethylphenyl)thiophene 
• 30548-83-5 (5-bromo-3,4-dinitro-thiophen-2-yl)-(4-nitro-phenyl)-amine 

Relevant articles and documents

Small band gap oligothieno[3,4-b]pyrazines

(Chemical Equation Presented) (Graph Presented) The synthesis and the optical and electrochemical properties of thiophene end capped oligo(2,3-alkylthieno[3,4-b]pyrazine)s are presented. The optical absorption rapidly shifts to lower energies with increasing chain length, caused in almost equal amounts by a rise of the HOMO and a lowering of the LUMO levels. The optical band gap of the polymer is estimated to be 1.13 ± 0.07 eV. Extrapolated redox potentials indicate that the polymer is a small band gap p-type material.

The effect of changes in π-conjugated terthienyl systems using thienyl and ethylenedioxybenzene functionalized thieno[3,4-b]pyrazine precursors: Multicolored low band gap polymers

New classes of thieno[3,4-b]pyrazines containing thienyl and ethylenedioxy phenyl units on electron-withdrawing moieties of π-conjugated terthienyl were synthesized. The effect of structural differences on electrochemical and optoelectronic properties of the resulting polymers was investigated. Changes in the electronic nature of the functional groups enable to tune the electrochemical properties of the π-conjugated terthienyl monomers by lowering oxidation potential from 0.62 V (DTTP) to 0.56 V (DBTP). Spectroelectrochemical analyses revealed that the neutral polymer (PDBTP) is dark green in its neutral state revealing π-π* transitions in two well-separated bands at 410 and 751 nm. The electronic band gap of polymer, defined as the onset of the π-π* transition, is found to be 1.0 eV. Using the thienyl unit instead of ethylenedioxy phenyl, a red shift in the band gap (0.95 eV) is observed. The polymer, PDTTP, exhibits multicolor electrochromism and can be switched between a dark yellow neutral state, a green intermediate state, and a brown oxidized state. PDBTP also shows a multicolored electrochromic behavior with three distinct states: dark green at the neutral state, a brown intermediate state, and a brown-violet oxidized state.

Donor-Acceptor-Donor Thienopyrazines via Pd-Catalyzed C-H Activation as NIR Fluorescent Materials

A series of thienopyrazine-based donor-acceptor-donor (D-A-D) near-infrared (NIR) fluorescent compounds were synthesized through a rapid, palladium-catalyzed C-H activation route. The dyes were studied through computational analysis, electrochemical prope

Nitration method of simple and efficient aromatic heterocyclic compound

The invention provides a nitration method of a simple and efficient aromatic heterocyclic compound, which is large in width, easy to operate and good in repeatability. By means of the method, high-efficiency nitration of common aromatic compounds is realized, the nitration efficiency is greatly improved, and the simple synthesis of the organic photoelectric material intermediate is realized.

Donor-Acceptor-Donor Thienopyrazine-Based Dyes as NIR-Emitting AIEgens

Organic Near-Infrared luminophores have found broad application as functional materials, but the development of efficient NIR emitters is still a challenging goal. Here we report on a new class of thieno[3,4-b]pyrazine-based NIR emitting materials with Aggregation Induced Emission (AIE) properties. The dyes feature a donor–acceptor–donor (D?A?D) structure, with a thienopyrazine acceptor core connected to two triarylamine donor groups bearing a tetraphenylethylene (TPE) moiety. Fast and efficient synthesis allowed the modular preparation of three dyes of tunable absorption and emission profiles. These constructs were extensively characterized by spectroscopic studies in different solvents, which revealed intense light-harvesting ability and emissions in the deep-red and NIR region with large Stokes shift values. Remarkably, the dyes exhibited AIE properties, retaining emissive ability in the aggregate state, thus emerging as attractive materials for their potential application in the development of luminescent devices.

Photocontrolled Synthesis of n-Type Conjugated Polymers

Current approaches to synthesize π-conjugated polymers (CPs) are dominated by thermally driven, transition-metal-mediated reactions. Herein we show that electron-deficient Grignard monomers readily polymerize under visible-light irradiation at room temperature in the absence of a catalyst. The product distribution can be tuned by the wavelength of irradiation based on the absorption of the polymer. Conversion studies are consistent with an uncontrolled chain-growth process; correspondingly, chain extension produces all-conjugated n-type block copolymers. Preliminary results demonstrate that the polymerization can be expanded to donor–acceptor alternating copolymers. We anticipate that this method can serve as a platform to access new architectures of n-type CPs without the need for transition-metal catalysis.

TRIPHENYLAMINE COMPOUNDS, POLYMERS MADE THEREFROM AND ELECTROCHROMIC DEVICE COMPRISING THE SAME

The present invention relates to a triphenylamine compound, to a polymer thereof and to an electrochromic device comprising the same, and specifically, to a triphenylamine compound represented by the chemical formula (1), to a polymer thereof and to an electrochromic device comprising the same. In the chemical formula (1), R, R1, R2, R3, R4, and R5 are as defined in claim 1. The present invention also provides a triphenylamine-based polymer capable of forming a thin film having uniform surface and exhibiting excellent reversibility in the electrochromic characteristics.COPYRIGHT KIPO 2018

In Situ Oxidation Synthesis of p-Type Composite with Narrow-Bandgap Small Organic Molecule Coating on Single-Walled Carbon Nanotube: Flexible Film and Thermoelectric Performance

Although composites of organic polymers or n-type small molecule/carbon nanotube (CNT) have achieved significant advances in thermoelectric (TE) applications, p-type TE composites of small organic molecules as thick surface coating layers on the surfaces of inorganic nanoparticles still remain a great challenge. Taking advantage of in situ oxidation reaction of thieno[3,4-b]pyrazine (TP) into TP di-N-oxide (TPNO) on single-walled CNT (SWCNT) surface, a novel synthesis strategy is proposed to achieve flexible films of TE composites with narrow-bandgap (1.19 eV) small molecule coating on SWCNT surface. The TE performance can be effectively enhanced and conveniently tuned by poly(sodium-p-styrenesulfonate) content, TPNO/SWCNT mass ratio, and posttreatment by various polar solvents. The maximum of the composite power factor at room temperature is 29.4 ± 1.0 μW m?1 K?2. The work presents a way to achieve flexible films of p-type small organic molecule/inorganic composites with clear surface coating morphology for TE application.

Synthesis and characterization of triphenylamine-based polymers and their application towards solid-state electrochromic cells

Four novel triphenylamine-based polymers, PJK1, PJK2, PJK3 and PJK4 were successfully synthesized and fully characterized by 1H NMR, UV-VIS spectroscopy, cyclic voltammetry (CV), GPC and spectroelectrochemistry. These polymers are easily soluble in many common organic solvents, which make them appropriate for film deposition via spray-coating. We fabricated electrochromic cells comprising ITO-coated glass/polymer/gel electrolyte/ITO-coated glass and patterned the color change by applying direct current with different voltages. We report herein color changes, from the neutral to oxidized form as follows: for PJK1, orange to dark green; for PJK2, light yellow to reddish brown; for PJK3, light blue to grey; and for PJK4, green to bluish green. The majority of the copolymers exhibited very good thermal stabilities, as evidenced by less than a 5% weight loss in temperatures exceeding 400 °C. To further characterize, we simulated the electrochemical and optical properties, which are good agreement with the experimental data.

π-electron conjugated compound, manufacturing method therefor, and π-electron conjugated polymer obtained using same

Provided are a π-electron conjugated polymer having a constitutional unit represented by general formula (2) that is suitable as an electrochromic material that changes from a desired colored state to a decolored state, a new compound that is a raw materi