3958-03-0

Basic information

• Product Name: Tetrabromothiophene
• Synonyms: 2,3,4,5-TETRABROMOTHIOPHENE;AKOS 93380;TETRABROMOTHIOPHENE, 99+%;Thiophene, tetrabromo-;2,3,4,5-TETRABROMOTHIOPHENE 98.0%MIN;Tetrabromothiophene ,98%;Tetrabromothiophene3;Tetrabromothiophene ReagentPlus(R), 99%
• CAS NO: 3958-03-0
• Molecular Formula: C₄Br₄S
• Molecular Weight: 399.72
• EINECS: 223-554-7
• Product Categories: Thiophenes;Thiophene&Benzothiophene;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiophenesBuilding Blocks;Building Blocks;C4 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-oher series
• Mol File: 3958-03-0.mol

Chemical Properties

• Melting Point: 116-118 °C(lit.)
• Boiling Point: 326 °C(lit.)
• Flash Point: 324-327°C
• Appearance: Cream to brown/Crystalline Powder
• Density: 2.836 (estimate)
• Vapor Pressure: 0.000422mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water. Soluble in organic solvents.
• BRN: 383664
• CAS DataBase Reference: Tetrabromothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabromothiophene(3958-03-0)
• EPA Substance Registry System: Tetrabromothiophene(3958-03-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: LIGHT SENSITIVE
• Hazardous Substances Data: 3958-03-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics and Photonics:
Tetrabromothiophene is used as a crucial component in the development and manufacturing of organic electronics and photonics. Its chemical properties make it a valuable addition to these fields, enhancing the performance and efficiency of the devices and systems.
Used in Organic Synthesis:
In the realm of organic synthesis, Tetrabromothiophene serves as an essential raw material and intermediate. Its unique structure and properties allow for the creation of a variety of complex organic compounds, contributing to the advancement of chemical research and development.
Used in Pharmaceuticals:
Tetrabromothiophene is also utilized in the pharmaceutical industry, where it plays a vital role in the synthesis of various drugs and medications. Its chemical properties enable the development of new and innovative pharmaceutical compounds, potentially leading to breakthroughs in medical treatments.
Used in Agrochemicals:
In the agrochemical sector, Tetrabromothiophene is employed as a key ingredient in the formulation of various agricultural chemicals. Its properties contribute to the effectiveness of these chemicals, helping to improve crop yields and protect plants from pests and diseases.
Used in Dyestuff:
Lastly, Tetrabromothiophene is used in the dyestuff industry, where it is an important component in the production of various dyes and pigments. Its unique properties allow for the creation of vibrant and long-lasting colors, enhancing the quality and appeal of the final products.

InChI:InChI=1/C4Br4S/c5-1-2(6)4(8)9-3(1)7

Upstream product

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• 7726-95-6 bromine 
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Downstream Products

• 872-31-1 3-Bromothiophene 
• 3141-26-2 3,4-dibromothiophene 
• 3141-25-1 2,3,4-tribromothiophene 
• 53317-05-8 3,4,5-tribromo-2-thiophene carboxylic acid 
• 608-37-7 dibromomaleic acid 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 106550-53-2 ethyl N-(3,4,5-tribromo-2-thienyl)-carbamate 
• 59-49-4 2-Benzoxazolinone 
• 90454-57-2 phenyl N-(3,4,5-tribromo-2-thienyl)-carbamate 
• 118012-98-9 1-(3,4,5-tribromothien-2-yl)-(1R,2S,5R)-menthol 
• 3141-24-0 2,3,5-tribromothiophene 
• 25373-20-0 3,4-dibromo-2,5-thiophenedicarboxaldehyde 
• 175658-90-9 3,4-dibromo-2,5-bis(trimethylsilanyl)thiophene 
• 30319-06-3 2,3,4-tribromo-5-methylthiophene 

Relevant articles and documents

Synthesis and mesomorphic behavior of novel liquid-crystalline thiophene derivatives

A new class of thiophene-based cholesteryl and ferrocenyl derivatives was synthesized and characterized by common analytical techniques. Liquid-crystalline properties were investigated by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). Thiophene-based cholesteryl derivatives show homeotropic liquid-crystalline phase sequence crystal → smectic A → cholesteric → isotropic, whereas the ferrocenyl derivative is nonmesomorphic. The effects of thiophene ring, terminal group, and length of the polymethylene spacers on the mesomorphic behavior are discussed. Copyright Taylor & Francis Group, LLC.

Design and Applications of a SO2 Surrogate in Palladium-Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines

A new SO2 surrogate is reported that is cheap, bench-stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two-chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.

Isomeric effect of fluorene-based fused-ring electron acceptors to achieve high-efficiency organic solar cells

Acceptor-donor-acceptor (A-D-A) non-fullerene electron acceptors (NFEAs) using ladder-type donor structures have become the dominant n-type materials for achieving high-efficiency OSCs. In this work, two isomeric fluorene-based ladder-type structures FCTT (TT-C-F-C-TT) and FTCT (T-C-TFT-C-T) have been designed and synthesized. These two isomeric donors with the different fused-ring arrangement, molecular geometry, and side-chain placement were end-capped with the FIC acceptors to form two NFEAs FCTT-FIC and FTCT-FIC isomeric materials. Compared to FTCT-FIC using the thiophene (T)-terminal donor, FCTT-FIC with the thienothiophene (TT)-terminal donor has more evenly distributed side chains on both sides of the backbone and less steric hindrance near the FIC acceptors, which enables stronger antiparallel π-π packing among the end-groups to create a channel for efficient electron transport, as evidenced by the thin-film GIWAXS measurements. FCTT-FIC displayed a larger optical bandgap and deeper-lying energy levels than its FTCT-FIC isomer. Compared to the PBDB-T:FTCT-FIC device, the PBDB-T:FCTT-FIC device showed a higher PCE of 10.32% with an enhanced Jsc of 19.63 mA cm-2 and an FF of 69.14%. A PM6:FCTT-FIC device using PM6 as a p-type polymer achieved the highest PCE of 12.23%. By introducing PC71BM as the second acceptor to enhance the absorption at shorter wavelengths, optimize the morphology and facilitate electron transport, the ternary-blend PM6:FCTT-FIC:PC71BM (1 : 1 : 0.5 in wt%) device yielded the highest PCE of 13.37% with a Voc of 0.92 V, a higher Jsc of 19.86 mA cm-2, and an FF of 73.2%. This result demonstrated that the TT-terminal ladder-type donor is generally a better molecular design than the corresponding T-terminal ladder-type isomer for the development of new A-D-A NFEAs.

From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4- c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag-In-Zn-S Nanocrystals

A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-D-SH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (λmax = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (λmax = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.

Utilizing Difluorinated Thiophene Units to Improve the Performance of Polymer Solar Cells

While there are numerous approaches to functionalize conjugated polymers for organic solar cells (OSCs), one widely adopted approach is fluorination. Of the many different locations for fluorination, one of the least studied is the conjugated linker which connects the donor and acceptor moieties; further, all existing reports primarily explore monofluorinated thiophene units. Herein, we synthesize and compare two conjugated polymers, HTAZ and DFT-HTAZ, which have different thiophene linkers. In HTAZ, a bare thiophene unit connects the donor and acceptor moieties, while DFT-HTAZ utilizes difluorinated thiophene (DFT) linkers. These polymers serve as the model system to explore the impact of DFT units in OSCs; additionally, this is the first publication to investigate polymers containing DFT units paired with non-fullerene acceptors. Compared to HTAZ, the incorporation of the DFT units maintained the optical properties while lowering the energy levels by a0.4 eV, which allowed for a much improved Voc value of a1 V. Importantly, when compared with the appropriate non-fullerene acceptor, DFT-HTAZ:ITIC-Th1 blends reached an efficiency of a10%, which is nearly 3× that of the nonfluorinated HTAZ. As most OSC polymers have thiophene linkers, using DFT units could serve as a proficient method to increase OSC performance in many polymer systems, especially those that do not have locations for functionalization on the acceptor moiety.

Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction

Derivatives of 3,4-ethylenedithiothiophene (EDTT) are reported starting from tetrabromothiophene. Selective 2,5-dilithiation followed by reaction with a range of aldehydes gives diols as mixtures of diastereomers. Only the 2 and 5 positions in thiophene react leaving the 3,4-bromides for further elaboration. The diols are oxidised to their corresponding diketones using activated MnO2. Reaction with 1,2-ethanedithiol, by addition-elimination, provides access to novel monomers for the preparation of conjugated copolymers of 3,4-ethylenedithiothiophene (EDTT). A range of these monomers can be attained by applying the synthesis of a series of ketones applicable to further synthesis of π-extended thiophene-based organic semiconductors. Finally, this new route was compared to 3,4-ethylenedioxythiophene (EDOT) dialdehyde derivatives synthesised by an alternative to literature chemistry.

Organic Dye and Dye-Sensitized Solar Cell

PURPOSE: An organic dye, photoelectric diode including the same and dye-sensitized solar battery are provided to have an absorbing band in long wavelength. CONSTITUTION: An organic dye is represented by chemical formula 1. A photoelectric diode includes porous oxide semiconductor membrane which includes the organic dye. A dye-sensitized solar cell comprises a first electrode, a second electrode which is formed on one side of the first electrode and includes a light absorptive layer, and electrolyte buried in a space between the first and second electrodes.

BLUE ELECTROCHROMIC COMPOUND, PREPARATION METHOD AND SUBASSEMBLY THEREOF

One class of blue thiophene electrochromic compounds include 3,4-(2,2-bis(2-oxo-3-phenylpropyl))propylenedioxythiophene, 3,4-(2,2-bis(2-oxo-3-phenylbutyl))propylenedioxythiophene, and 3,4-(2,2-bis(2-oxo-3-phenylamyl))propylenedioxythiophene. The thiophene electrochromic compounds can change color between blue and transparency. The thiophene compounds can be electropolymerized on the surface of the ITO glass to form a film. The film has characteristics of low driving voltage (within ±1V), fast response time, and large transmittance difference between colored-state and bleached-state (up to 77.5%). The thiophene electrochromic compounds can be used in the electrochromic window, rearview mirror, electrochomeric display, and the like.

ORGANIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE DEVICE INCLUDING THE SAME

The present invention relates to a novel organic compound and an organic light emitting device using the same, and more specifically, to a novel organic compound which has electrical stability, high electrical transport ability and light emitting ability, and high glass transition temperature, and can prevent crystallization, and to an organic light emitting device using an organic layer including the same.COPYRIGHT KIPO 2015

Plasmonic hybrid nanotubes of fullerene C60-polythiophene-silver or gold nanoparticles: Fabrication and enhancement of the Raman scattering

We determined the surface-enhanced Raman scattering of the plasmonic hybrid nanotubes of fullerene C60-polythiophene-Ag or Au nanoparticles (NPs) which were synthesized via the template-based electrocopolymerization of terthiophene-linked fullerene C60 and terthiophene-modified Ag NPs or Au NPs using a nanoporous alumina membrane as the template. The combination of plasmonic activity and chemical stability may allow for a variety of new applications.