13191-36-1

Usage

Uses

Used in Chemical Synthesis:
2,5-DIBROMO-3-METHYLTHIOPHENE is used as a building block for the chemical synthesis of various compounds. Its unique structure allows for the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-DIBROMO-3-METHYLTHIOPHENE is used as a key intermediate in the development of new drugs. Its chemical properties enable the synthesis of molecules with potential therapeutic effects, contributing to the advancement of medical treatments.
Used in Material Science:
2,5-DIBROMO-3-METHYLTHIOPHENE is also utilized in the field of material science for the development of novel materials with specific properties. Its incorporation into polymers and other materials can lead to improved performance characteristics, such as enhanced stability, reactivity, or conductivity.
Used in Agrochemical Industry:
In the agrochemical industry, 2,5-DIBROMO-3-METHYLTHIOPHENE serves as a crucial component in the synthesis of various pesticides and other agricultural chemicals. Its unique structure allows for the development of compounds with targeted effects on pests, helping to improve crop protection and yield.
Overall, 2,5-DIBROMO-3-METHYLTHIOPHENE is a versatile compound with a wide range of applications across different industries, primarily due to its unique chemical structure and its role as a building block in the synthesis of various compounds.

InChI:InChI=1/C5H4Br2S/c1-3-2-4(6)8-5(3)7/h2H,1H3

Upstream product

• 616-44-4 3-Methylthiophene 

Downstream Products

• 492-97-7 2,2'-Bithiophene 
• 113386-76-8 3'-methyl-2,2':5',2-terthiophene 
• 1193524-70-7 3,3'-[3-methylthiene-2,5-diyl]diphenol 
• 1435937-73-7 (5-bromo-4-methylthiophen-2-yl)(thiophen-2-yl)methanone 
• 1612854-92-8 C₃₁H₃₇BrN₄O₃S 
• 1612854-93-9 C₅₀H₆₀N₈O₇S 
• 40808-46-6 4-methyl-2,5-diphenylthiophene, 
• 439901-89-0 triphenyl((2,5-dibromothiophen-3-yl)methyl)phosphonium bromide 
• 1111095-99-8 2-(5-bromo-4-methylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Synthesis and properties of regioregular poly(3-substituted thiophene) bearing disiloxane moiety in the substituent. remarkably high solubility in hexane

Regioregular poly(3-substituted thiophene) derivative bearing pentamethyldisiloxane moiety at the 3-substituent is prepared by nickel-catalyzed polymerization reactions with dehydrobrominative or debrominative generation of the organometallic monomer. The monomer precursors 2-bromo-3-(4- pentamethyldisiloxybutan-1-yl)thiophene (1a) and 2,5-dibromo- 3-(4-pentamethyldisiloxybutan-1-yl)thiophene (1b) are prepared from 3-methylthiophene with 45 steps in overall good yields. Treatment of 1a with TMPMgCl￠LiCl at room temperature for 3 h forms an organometallic monomer and following the addition of a nickel catalyst affords the corresponding polythiophene bearing a disiloxane moiety in the side chain. The reaction of 1b with Grignard reagent leads to the similar monomer and addition of a catalytic amount of [NiCl2(dppe)] also affords polythiophene in highly regioregular manners. The obtained polythiophene is found to be dissolved in a hydrocarbon such as hexane.

Poly[3-(5-octyl-thienylene-vinyl)-thiophene]: A side-chain conjugated polymer with very broad absorption band

A novel polythiophene derivative, poly[3-(5-octyl-thienylene-vinyl)- thiophene] (POTVT) with conjugated thienylene vinyl side-chain, was synthesized, and the POTVT film shows a very broad absorption band-width covering from 300 nm to 700 nm after thermal annealing at 130°C for 10 min. The Royal Society of Chemistry 2006.

Control of vertical distribution of thiophene-based copolymers containing 4,7-Dithien-2-yl-benzo[C][1,2,5]thiadiazole and 3,6-Dithien-2-yl-pyrrolo[3,4-C]pyrrole-1,4(2H,5H)-dione as Side Groups for Photovoltaics

Four new D—A type copolymers with 2D-conjugated side-chain identified PfToBT, PbToBT, PfTDPP and PbTDPP, containing two acceptors 4,7-dithien-2-yl-benzo[c][1,2,5]thiadiazole (DTBT), and diketopyrrolopyrrole (DPP) linked by thiophene donors, are obtained using Pd-catalyzed Stille-coupling reaction. These polymers show a broad visible-near-infrared absorption band (Eg?=?1.79–1.66?eV) and possess a relatively low-lying HOMO level at ?5.34 to ?5.12?eV. All the polymer:PC70BM blend films showed edge-on structure and have similar dπ-spacing values. According to the structure of conjugated side-chain, the vertical distributions of polymer chains and PC70BM within the BHJ (bulk heterojunction) were different. When DPP used as an acceptor, conjugated side chains of the polymer coexisted with PC70BM in same position. The BHJ film prepared from PfToBT, PbToBT had a discontinuous network between polymer and PC70BM, whereas films from PfTDPP and PbTDPP formed continuous and evenly distributed network between them. This optimized vertical morphology promotes hole transport along respective pathways of polymers and fullerenes in the vertical direction, leading to high JSC. PbTDPP shows PCE up to 2.9% (Jsc of 9.4?mA/cm2, Voc of 0.68 V, and FF of 0.44).

New carbazole-based conjugated polymers containing pyridylvinyl thiophene units for polymer solar cell applications: Morphological stabilization through hydrogen bonding

We have synthesized two conjugated polymers (P1, P2) containing alternating electron-donating and -accepting units, based on N-alkyl-2,7-carbazole, 4,7-di(thiophen-5-yl)-2,1,3-benzothiadiazole and 3-[2-(4-pyridyl)vinyl]thiophene units. These conjugated polymers contained different contents of pyridine units, which were incorporated to form hydrogen bonds with [6,6]-phenyl-C 61-butyric acid (PCBA). When these hydrogen bonding interactions were present in the polymer thin films, their thermal stability improved; deterioration, which occurred through aggregation of PCBA methyl ester after lengthy annealing times, was also suppressed. The power conversion efficiency of a device incorporating the film featuring hydrogen bonding interactions remained at 75% of the original value after thermal annealing for 5 h at 140 °C.

Use of poly(3-methylthio)thiophene blends for direct laser tracing and bulk heterojunction solar cells

In this article we demonstrate the use of a blend made of two regioregular polythiophenic derivatives, namely poly(3-methylthio)thiophene and poly(3-hexyl)thiophene, to obtain conductive traces by the simple laser exposure of their thin films to a suitable laser source. The polymeric blend was also tested as a photoactive layer for BHJ solar cells, showing an improved surface morphology and a wider absorption spectrum, thus resulting in an enhanced photovoltaic performance. In the standard condition normally used for the cell preparation, we obtained a 3.16% power conversion efficiency. The device showed good reproducibility and stability over time.

A study on regulating the conjugate position of NLO chromophores for reducing the dipole moment and enhancing the electro-optic activities of organic materials

In order to improve the first-order hyperpolarizability (β) of the chromophore and transform it into a high macroscopic electro-optic activity, a series of novel second-order nonlinear optical chromophores with different push-pull electron groups introduced on the thiophene π-conjugate bridge for tuning the shape and dipole moment (μ) of chromophores were designed and synthesized. These chromophores are based on the same thiophene π-conjugated bridge, where the donor (N,N-diethylaniline) and acceptor (2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile or malononitrile) are linked to positions 2 and 3 of thiophene, respectively, affording a boomerang-like shape instead of a rod-like shape. Besides, an electron-poor group, Br (bromine atom), or an electron-rich group, DEA (N,N-diethylaniline), as an auxiliary acceptor or donor are linked to position 5 of thiophene. In addition, all chromophores showed good thermal stability as per the results from the DSC and TGA analysis. Through UV-vis analysis and DFT calculation, it has been concluded that chromophores with additional electron-rich groups as auxiliary donors display better intermolecular charge-transfer (ICT) absorption and lower HOMO-LUMO energy gaps (ΔE). Furthermore, the boomerang-like chromophore with the same push-pull structure shows a smaller dipole moment (μ) and β value than the traditional FTC. The poling results of guest-host EO polymers FTC/APC, FTC-H/APC, FTC-Br/APC and FTC-DEA/APC with the same number density afford r33 values of 17 pm V-1, 11 pm V-1, 10 pm V-1 and 25 pm V-1, respectively. Although the β value of FTC-DEA is smaller than that of FTC, the r33 value of FTC-DEA (25 pm V-1) is 47% greater than that of FTC (17 pm V-1) under the same number density. Hence, the above-mentioned results indicated that regulating the conjugate position of chromophores can efficiently decrease the dipole moment of the chromophores, weakening the dipole-dipole interactions and thereby enhancing the macroscopic electro-optical activity of poled polymers. These results indicate the potential application of these novel chromophores in electro-optical devices.

1,2,3-Triazolyl functionalized thiophene, carbazole and fluorene based A-: Alt -B type π-conjugated copolymers for the sensitive and selective detection of aqueous and vapor phase nitroaromatics (NACs)

A series of highly emissive π-conjugated A-alt-B type copolymers (P1-P3) appended with a 1,2,3-triazole moiety was synthesized via Suzuki polymerization. The well-defined and soluble π-conjugated copolymers were characterized via multinuclear NMR spectroscopy and tetradetector GPC studies, showing a molecular weight (Mn) in the range of 16.4-20.1 kDa with a polydispersity index in the range of 1.25-1.42. The synthesized emissive π-conjugated polymer probes were explored as fluorescent chemosensors for nitroaromatic compounds (NACs) in solution, vapor and contact mode. Detailed photophysical and sensing studies were performed to understand the polymer-NAC interaction, inducing the selective fluorescence quenching of the π-conjugated polymer probes through the photoinduced electron transfer (PET) mechanism. All the polymeric probes (P1-P3) were highly reversible in nature with NACs, and thus could be reused multiple times. The limit of detection of the probes towards nitroaromatics was found to be in the range of 120-200 ppb with a high association constant in the order of 104 M-1. Furthermore, test paper kits were also fabricated, which allowed the trace detection of picric acid by the naked eye, making it a practical means for the quick, easy and inexpensive on-site detection of NAC-based explosives.

Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling

A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity of this approach is demonstrated with the preparation of discreet oligothiophenes with up to 10 thiophene repeat units. Symmetrical oligothiophenes are prototypical organic semiconductors where their molecular electrical doping as a function of the chain length can be assessed spectroscopically. An oligothiophene critical length for integer charge transfer was observed to be 10 thiophene units, highlighting the potential use of discrete oligothiophenes as doped conduction or injection layers in organic electronics applications.

Preparation method 2, 5 - dibromo -3 - methylthiophene

The invention discloses a preparation method of 2,5-dibromo-3-thiotolene shown as a formula (II). The method comprises the followings steps that the preparation method of the 2,5-dibromo-3-thiotolene shown as the formula (II) is characterized in that the method is performed through the following steps that 3-thiotolene shown as a formula (I) is used as a raw material; a brominating agent of potassium bromide is added; the mixture is stirred and mixed uniformly in a mixed solution of acetic acid and water; a brominating agent of ZnAl-BrO3-LDHs is slowly added at 10 to 50 DEG C; continuous stirring is performed for reaction for 2h; obtained reaction liquid is subjected to aftertreatment to obtain the 2,5-dibromo-3-thiotolene shown as the formula (II); the mass quantity ratio of the 3-thiotolene shown as the formula (I) to the ZnAl-BrO3-LDHs to the potassium bromide is 1:1.3:(1.6 to 1.9). The preparation method has the advantages that the reaction conditions are mild; the used brominating reagent is a solid matter, is cheap, is easily obtained and achieves an environment-friendly effect; the reaction operation is simple; the aftertreatment is convenient; the target product yield is high; the side reactions are few. The formulas are shown in the specification.

THIOPHENE, MANUFACTURING METHOD THEREOF, AND PHARMACEUTICAL APPLICATION OF SAME

The present invention discloses a thiophene used as a uric acid transporter (URAT1) inhibitor and applicantion of the thiophene in preparing a pharmaceutical product for treating a disease related to abnormal uric acid levels, specifically in preparing a pharmaceutical product for treating hyperuricemia and gouty arthritis. The invention specifically relates to a compound as represented by formula (I) or a pharmaceutically acceptable salt thereof.