3140-93-0

Basic information

• Product Name: 2,3-Dibromothiophene
• Synonyms: 2,3-DibroMothiophene 98%, 3-DibroMothiophene 98%;BUTTPARK 146\50-38;2,3-DIBROMOTHIOPHENE;AKOS 91257;2,3-Dibromothiophene, 98+%;2,3-Dibromothiophene,97%;Thiophene, 2,3-dibromo-;2,3-Dibromothiophene 98%
• CAS NO: 3140-93-0
• Molecular Formula: C₄H₂Br₂S
• Molecular Weight: 241.93
• EINECS: 221-542-6
• Product Categories: Heterocycle-oher series;Thiophenes;Thiophene&Benzothiophene;Miscellaneous;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiophenesBuilding Blocks;Thiophene Series;Heterocycles;Sulfur & Selenium Compounds;Building Blocks;C4 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 3140-93-0.mol

Chemical Properties

• Melting Point: -17.5°C
• Boiling Point: 218-219 °C(lit.)
• Flash Point: 125 °F
• Appearance: /liquid
• Density: 2.137 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: n20/D 1.632(lit.)
• Storage Temp.: Flammables area
• Sensitive: Light Sensitive
• BRN: 107512
• CAS DataBase Reference: 2,3-Dibromothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromothiophene(3140-93-0)
• EPA Substance Registry System: 2,3-Dibromothiophene(3140-93-0)

Safety Data

• Hazard Codes: Xn,F,Xi,T
• Statements: 10-36/37/38-20/21/22-36-25
• Safety Statements: 23-24/25-36/37/39-26-16-36-45
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 8
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 3140-93-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-Dibromothiophene is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a versatile building block for the creation of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-Dibromothiophene is used as a starting material for the development of novel therapeutic agents. Its chemical properties enable the synthesis of new drug candidates with potential applications in treating various diseases and medical conditions.
Used in Chemical Research:
2,3-Dibromothiophene is also utilized in chemical research as a model compound for studying the reactivity and properties of thiophene derivatives. This helps researchers gain a deeper understanding of the structure-activity relationships in thiophene chemistry, which can lead to the discovery of new compounds with improved properties and applications.
Used in Material Science:
In the field of material science, 2,3-Dibromothiophene can be used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can result in products with enhanced performance characteristics, such as improved stability, conductivity, or optical properties.

InChI:InChI=1/C4H2Br2S/c5-3-1-2-7-4(3)6/h1-2H

Upstream product

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Downstream Products

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Relevant articles and documents

Synthesis, optical and electrochemical properties new donor-acceptor (D-A) copolymers based on benzo [1,2-b:3,4-b′:6,5-b″] trithiophene donor and different acceptor units: Application as donor for photovoltaic devices

Two new conjugated D-A polymers P3 (PBTT-d-BTT) and P4 (PBTT-d-TPD) based on same benzo[1,2-b:3,4-b′:6,5-b″] trithiophene (BTT) donor and different acceptors monomers 5,8-dibromo-2-dodecanoylbenzo[1,2-b:3,4-b′:6,5-b″] trithiophene (d-BTT), and 1,3-dibromo-5-(2-ethylhexyl)thieno[3,4]pyrrol-4,6-dione (d-TPD) respectively, were synthesized by Stille cross-coupling reaction and characterized by gel permeation chromatography (GPC), 1H NMR, UV-Vis absorption, thermal analysis and electrochemical cyclic voltammetry (CV) tests. Photovoltaic properties of the polymers were studied by using the polymers as donor and PC71BM as acceptor with a weight ratio of polymer:PC71BM 1:1, 1:2 and 1:2.5. The optimized photovoltaic device was fabricated with an active layer of a blend P3:PC71BM and P4:PC71BM with a blend ratio of 1:2 showed PCE 3.16% and 2.42%, respectively under illumination of AM 1.5 at 100 mW/cm2 with solar simulator. The PCE of the device based on P3:PC71BM processed with DIO/o-DCB has been further improved up to 4.64% with Jsc of 10.52 mA/cm2 and FF of 0.58 attributed to the increase in crystalline nature of active layer and more balanced charge transport in the device, induced by DIO additive.

Synthesis and photovoltaic properties of new donor-acceptor (D-A) copolymers based on benzo[1,2-b:3,4-b′:6,5-b′′] trithiophene donor and different acceptor units (P1 and P2)

Two new conjugated D-A copolymers P1 (PBTT-TQ) and P2 (PBTT-TPz) based on the same benzo[1,2-b:3,4-b′:6,5-b′′] trithiophene (BTT) donor and different acceptor monomers 4,9-bis(5-bromithiophen-2-yl)-6,7-bis(2-ethylhexyl)[1,2,5] thiadiazolo[3,4-g] quinoxaline (TQ) and 5,7-bis(5-bromothiophen-2-yl)-2,3-bis(5-octylthiophen-2-yl) thieno[3,4-b] pyrazine (TPy), respectively, were synthesized by Stille cross-coupling reaction and characterized by gel permeation chromatography (GPC), 1H NMR, UV-Vis absorption, thermal analysis and electrochemical cyclic voltammetry (CV) tests. The optical bandgaps of P1 and P2 measured from the onset of optical absorption of these copolymers in thin films were 1.14 eV and 1.38 eV, respectively. Photovoltaic properties of the bulk heterojunction (BHJ) devices were studied using P1 and P2 as the donor and PC61BM or PC71BM as the acceptor with weight ratios of polymer:PC61BM of 1:1, 1:2 and 1:3. The optimized photovoltaic devices fabricated with active blend layers of P1:PC71BM (1:2) and P2:PC71BM (1:2) cast from o-diclorobenzene (o-DCB) showed PCEs of 2.05% and 3.14%, respectively, whereas P2:PC61BM and P2:PC71BM yielded PCEs of 1.44% and 2.11%, respectively. The PCEs of BHJ solar cells based on P1:PC71BM and P2:PC71BM processed from 1-chloronapthanene (CN)/o-DCB solvent were further improved up to 5.28% and 2.6%, respectively. This journal is

BIARYL HYDROXYTHIOPHENE GROUP IV TRANSITION METAL POLYMERIZATION CATALYSTS WITH CHAIN TRANSFER CAPABILITY

Catalyst systems that include a chain transfer agent and a metal-ligand complex according to formula (I).

Sterics vs electronics: Revisiting the catalytic regioselective hydrodebromination of 2,3,5-tribromothiophene

The application of sterically hindered palladium catalysts to the regioselective hydrodebromination of 2,3,5-tribromothiophene has been studied in detail, including the effects of catalyst choice, solvent, reaction time, and temperature, as well as the method of NaBH4 addition and the role of chelating additives to effect NaBH4 solubility. Ultimately it was determined that the background reaction between NaBH4 and bromothiophenes is too facile to allow both total conversion and high selectivity. Optimized conditions finally allowed a selectivity of ca. 16:1 with overall conversion of 100%. However, complications of overdebromination under these conditions still limit the yield of the desired 2,3-dibromothiophene to 65%.

Synthesis, optical and electrochemical properties new donor-acceptor (D-A) copolymers based on benzo[1,2-b:3,4-b′:6,5-b″] trithiophene donor and different acceptor units: Application as donor for photovoltaic devices

Two new conjugated D-A polymers P3 (PBTT-d-BTT) and P4 (PBTT-d-TPD) based on same benzo[1,2-b:3,4-b′:6,5-b″] trithiophene (BTT) donor and different acceptors monomers 5,8-dibromo-2-dodecanoylbenzo[1,2-b:3,4-b′:6,5-b″] trithiophene (d-BTT), and 1,3-dibromo-5-(2-ethylhexyl)thieno[3,4]pyrrol-4,6-dione (d-TPD) respectively, were synthesized by Stille cross-coupling reaction and characterized by gel permeation chromatography (GPC), 1H NMR, UV-Vis absorption, thermal analysis and electrochemical cyclic voltammetry (CV) tests. Photovoltaic properties of the polymers were studied by using the polymers as donor and PC71BM as acceptor with a weight ratio of polymer:PC71BM 1:1, 1:2 and 1:2.5. The optimized photovoltaic device was fabricated with an active layer of a blend P3:PC71BM and P4:PC71BM with a blend ratio of 1:2 showed PCE 3.16% and 2.42%, respectively under illumination of AM 1.5 at 100 mW/cm2 with solar simulator. The PCE of the device based on P3:PC71BM processed with DIO/o-DCB has been further improved up to 4.64% with Jsc of 10.52 mA/cm2 and FF of 0.58 attributed to the increase in crystalline nature of active layer and more balanced charge transport in the device, induced by DIO additive.

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent

The green generation of X+ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alcohol, nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochemistry were very similar to reactions involving N-bromosuccinimide in tetrahydrofuran solvent.

Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives

The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay.

Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation

Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.

Synthesis of 3,4′-dibromo-2,2′-bithiophene: A useful intermediate for 3,4′-disubstituted 2,2′-bithiophenes. X-ray molecular structure of 3,4′-dibromo-2,2′-bithiophene

The first synthesis of 3,4′-dibromo-2,2′-bithiophene via metal-catalysed cross-coupling between a metallated and a halogenated thiophene derivative is described. An X-ray crystal structure of 3,4′-dibromo-2,2′-bithiophene is reported. 3,4′-Dibromo-2,2′-bithiophene was converted into corresponding bis(alkylsulfanyl) derivatives through bromine-lithium exchange, followed by reaction with two dialkyl disulfides (Me2S2 or Bu2S2). The 1H and 13C NMR data are discussed.

Regioselective Debromination of 2,3,5-Tribromothiophene: A Facile Synthesis of Isomerically Pure 2,3- and 2,4-Dibromothiophene

The regioselective preparative debromination of 2,3,5-tribromothiophene to isomerically pure 2,3- and 2,4-dibromothiophene was effected by the use of sodium borohydride in the presence and absence of transition metal catalyst using predetermined optimum conditions from GC trials.