59311-27-2

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromo-5-bromomethylthiophene is utilized as a key intermediate in the production of pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical industry, 2-Bromo-5-bromomethylthiophene serves as an essential component in the synthesis of various agrochemicals. Its reactivity and structural features enable the creation of effective compounds for crop protection and pest management.
Used in Organic Material Synthesis:
2-Bromo-5-bromomethylthiophene is employed as a building block in the synthesis of organic materials. Its properties facilitate the development of new materials with potential applications in various industries, such as electronics, plastics, and coatings.
Used as a Reagent in Organic Synthesis:
2-Bromo-5-bromomethylthiophene also functions as a reagent in organic synthesis, where it can be used to modify or create new organic compounds. Its reactivity allows for a wide range of chemical reactions, expanding the scope of organic chemistry.
Used in Material Development:
2-Bromo-5-bromomethylthiophene is involved in the development of new materials with potential applications across various industries. Its unique structure and reactivity contribute to the creation of innovative materials with enhanced properties and functionalities.

Upstream product

• 1003-09-4 2-bromothiophene 
• 50-00-0 formaldehyd 
• 765-58-2 2-bromo-5-methyl thiophene 
• 79387-71-6 (5-bromothien-2-yl)methanol 
• 554-14-3 2-Methylthiophene 

Downstream Products

• 1030825-20-7 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide 
• 1188918-40-2 N-[((5S)-3-{3-fluoro-4-[5-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)-2-thienyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
• 669065-69-4 5-[2-[4-(dibutylamino)phenyl]vinyl]thiophene-2-carboaldehyde 
• 958007-17-5 4-{2,5-bis(2-ethylhexyloxy)-4-[(E)-2-(5-bromothiophen-2-yl)vinyl]styryl}-N,N-diethylphenylamine 
• 958007-19-7 5-{2,5-bis(2-ethylhexyloxy)-4-[4-(diethylamino)styryl]styryl}thiophene-2-carbaldehyde 

Relevant academic research and scientific papers

Model compounds based on poly(p-phenylenevinyleneborane) and terthiophene: Investigating the p-n junction in diblock copolymers

Conjugated block copolymers represent a class of materials with potential applications in electronics and optoelectronics. Three block copolymer model compounds were made by first synthesizing 5-ethynyl-2,2′:5′, 2″-terthiophene, 5-(2-propynyl)-2,2′:5′,2″-terthiophene and 5-(3-butynyl)-2,2′:5′,2″-terthiophene and then performing hydroboration polymerization from the alkyne of the terthiophene. The impact of the connectivity between the polymer blocks of these compounds was investigated. Theoretical and experimental studies indicated that charge transfer was occurring within the all-conjugated copolymer model compound, and that electronic coupling decreased with increasing length of the linking bridge between the n-type and p-type materials. Preliminary efforts to synthesize the related regioregular poly(3-hexylthiophene) all-conjugated diblock copolymer and use this material as the active layer in photovoltaic cells are discussed.

The A-D-A type small molecules with isomeric benzodithiophene cores: Synthesis and influence of isomers on photoelectronic properties

Two isomeric A-D-A type small molecules (SMs) of BDTx-2TVTDPP and BDTy-2TVTDPP were designed and synthesized, which contain different donor (D) center of substituted benzodithiophene (BDT) in backbone, and the same acceptor (A) and bridged units of diketopyrrolopyrrole (DPP) and thienylenevinylenethiophene (TVT), respectively. Their thermal stability, crystallinity, film morphology and photoelectronic properties were primarily investigated. It was found the BDTx-2TVTDPP with 2,6-substituted BDT unit exhibited a pronouncedly red-shifted and enhanced absorption in solid state and a better crystallinity. In contrast, the BDTy-2TVTDPP with 4,8-substituted BDT unit in backbone exhibited better solubility, deeper HOMO energy level and more smoothed blend film morphology. As a result, the solution-processing BDTy-2TVTDPP based solar cells displayed better photovoltaic properties than the BDTx-2TVTDPP based ones using fullerene derivatives (PC61BM or PC71BM) as electron acceptor. A power conversion efficiency maximum of 2.85% was obtained in the BDTy-2TVTDPP based cells, which is 1.8 times that of the BDTx-2TVTDPP based cells. This study indicates that changing the substituted positions of BDT is available to significantly improve photovoltaic properties for its resulting SMs.

Preparation method of 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene

The invention belongs to the field of chemistry, and particularly relates to a novel synthesis method of a key intermediate 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene for preparinga medicine canagliflozin for treating type 2 diabetes mellitus. Cheap and easily available 2-methylthiophene used as an initial raw material undergoes five steps of halogenation, p-nitrotoluene alkylation, coupling, nitro reduction and a Sandmeyer reaction to prepare the product. The method has the characteristics of simplicity in operation, high reaction selectivity, few byproducts and high product quality.

Fine tuning of the photovoltaic properties of triarylethylene-bridged dyes by altering the position and proportion of phenyl/thienyl groups

Four triarylethylene (TAE) π-spacers have been applied for Y-shaped dyes in dye-sensitized solar cells (DSSCs) and their effects on photovoltaic performance have been fully investigated. All photosensitizers inherit the ability of three-dimensional TAE to weaken the π-π stacking in aggregation state, while their suppression on charge recombination in electrolytes presents a high reliance on the position and proportion of phenyl/thienyl groups embedded in TAE moieties. In iodine electrolytes, benzene-rich triphenylethene-based dye JY65 achieves the best open-circuit voltage of 739 mV, sharply higher than that of 614 mV for trithienylethene (TTE)-based dye JY63. Moreover, dyes JY64 and D-1 with hetero-TAE-bridge tend to show better power convention efficiency (PCE) stemming from the higher short-circuit current density and moderate open-circuit voltage. Whereas in cobalt electrolytes, the TTE-bridged JY63 attains a superior PCE of 5.84%, inversely surpassing the value of 5.28% based on D-1 under the same condition. Therefore, tuning the TAE skeletons via altering the position and proportion of aryl groups in it would bring in a promising design for anti-stacking sensitizers to meet the varied demand in DSSCs.

Vinyl-triarylated amine conjugated charge transportation material and preparation method thereof

The invention discloses a vinyl-triarylated amine conjugated charge transportation material and a preparation method thereof. The chemical structural formula of the vinyl-triarylated amine conjugated charge transportation material is shown in the formula

Solution processable star-shaped molecules with a triazine core and branching thienylenevinylenes for bulk heterojunction solar cells

Two new star-shaped A-π-D molecules with triazine as a core and an acceptor unit, thienylenevinylene as the π bridge, and tert-butyl-substituted triphenylamine (tTPA)- or carbazole (tCz) as the end group and donor units of TTVTPA and TTVCz were synthesized for their application as donor materials in solution processed bulk heterojunction organic solar cells (OSCs). The charge transfer was convergent from peripheral groups to the central core along the conjugated branches in these star-shaped molecules (SSMs). TTVTPA and TTVCz are soluble in common organic solvents. Excellent thermal stability was observed for TTVTPA and TTVCz. OSCs were fabricated by spin-coating a blend of each SSM with the fullerene derivatives (PC61BM or PC71BM) as a composite film-type photoactive layer. The PV properties of the TTVTPA/fullerene derivative based OSCs were considerably better than those of the TTVCz/fullerene derivative blend based OSCs. A power conversion efficiency of 2.48%, a short-circuit current density of 10.57 mA cm-2, an open-circuit voltage of 0.69 V, and a fill factor of 0.34 were observed for the OSC based on the active layer of TTVTPA/PC71BM (1:7, w/w). This journal is

Amino group-containing heterocyclic derivatives and sensitizing dyes for photoelectric conversion containing the heterocyclic derivatives

It is intended to provide novel amino group-containing heterocyclic derivatives, which have a broad absorption zone in the visible region and are suitable for sensitizing dyes for photoelectric conversion having a high photoelectric conversion efficiency,

Steric effects of the initiator substituent position on the externally initiated polymerization of 2-bromo-5-iodo-3-hexylthiophene

Externally initiated polymerization of 2-bromo-3-hexyl-5-iodothiophene was attempted from four aryl and thiophene based small molecule initiators functionalized with a phosphonate moiety. Initiated poly(3-hexylthiophene) product was obtained in various yields depending on the nature of the initiating molecule. Reaction intermediates for the oxidative addition and the ligand exchange steps were analyzed utilizing both experimental and theoretical methods. It was observed that an ortho substituent plays a crucial role in the outcome of the polymerization mechanism and that aryl based initiators are generally more stable than thiophene based initiators. Density functional theory (DFT) calculations revealed the importance of the steric effects on the success of the externally initiated chain growth polymerization mechanism.

Synthesis, structures, and optical and electrochemical characteristics of novel crown-containing polythiophene systems

The synthesis, structures, and optical and electrochemical characteristics of novel crown-containing styryl mono-and polythiophenes were described. The double bonds were constructed by the Horner-Wadsworth-Emmons method. The Suzuki and Stille cross-coupling reactions were used to create polythiophene chains. Optical measurements revealed intense absorption and fluorescence of crown-containing polythiophenes; the band positions and shapes in their absorption and emission spectra depend on the structure of the polythiophene. The electrochemical characteristics of the compounds obtained were measured.

Push-pull chromophore with phenylene and thiophene as conjugation bridge for electro-optic applications

We designed and synthesized a push-pull type chromophore (PT-TCF) containing phenylene and thiophene ring as a conjugation bridge. Bulky alkyl chain was substituted into the phenylene bridge to minimize the intermolecular interaction among the neighbor mo