930-96-1

Basic information

• Product Name: 3-Bromothiophene-2-carbaldehyde
• Synonyms: BUTTPARK 43\57-52;3-BROMOTHIOPHENE-2-CARBOXALDEHYDE;3-BROMOTHIOPHENE-2-CARBALDEHYDE;3-BROMO-2-FORMYLTHIOPHENE;3-BROMO-2-THIOPHENECARBALDEHYDE;3-Bromothiophene-2-carboxaldehyde, 95%+;3-Bromo-2-Formylthophene;3-Bromothiophene-2-carboxaldehyde, GC 97%
• CAS NO: 930-96-1
• Molecular Formula: C₅H₃BrOS
• Molecular Weight: 191.05
• EINECS: -0
• Product Categories: Azoles;blocks;Bromides;Thiophene&Benzothiophene;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Aldehydes;Building Blocks;C1 to C6;C4 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Thiophenes
• Mol File: 930-96-1.mol

Chemical Properties

• Melting Point: 25 °C
• Boiling Point: 77-79°C 0,2mm
• Flash Point: 110-113°C/10mm
• Appearance: /
• Density: 1,8 g/cm3
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.6377
• Storage Temp.: Refrigerator
• Water Solubility: Not miscible in water.
• Sensitive: Air Sensitive
• BRN: 109757
• CAS DataBase Reference: 3-Bromothiophene-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromothiophene-2-carbaldehyde(930-96-1)
• EPA Substance Registry System: 3-Bromothiophene-2-carbaldehyde(930-96-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-22-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 930-96-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromothiophene-2-carbaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its reactivity and functional groups make it a versatile building block for creating a wide range of molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Bromothiophene-2-carbaldehyde is used as a starting material for the development of new drugs. Its unique structure allows for the creation of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemicals:
3-Bromothiophene-2-carbaldehyde is utilized in the agrochemical industry for the production of pesticides, herbicides, and other crop protection agents. Its chemical properties enable the development of effective and targeted solutions for managing pests and diseases in agriculture.
Used in Dye Industry:
In the dye industry, 3-Bromothiophene-2-carbaldehyde is employed as a precursor for the synthesis of various dyes and pigments. Its ability to form stable chromophores makes it a valuable component in the creation of vibrant and long-lasting colorants for textiles, plastics, and other materials.

InChI:InChI=1/C5H3BrOS/c6-4-1-2-8-5(4)3-7/h1-3H

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Relevant articles and documents

A convenient preparation of thieno[3,2-c]pyrazole 1

A practical synthesis of multigram quantities of 1H-thi-eno[3,2-c]pyrazole is presented in which the Jacobson reaction serves as the key step. Georg Thieme Verlag Stuttgart · New York.

INDACENO DERIVATIVES AS ORGANIC SEMICONDUCTORS

The present invention provides compounds comprising at least one unit of formula (1) or (1') as well as a process for the preparation of the compounds, intermediates of this process, electronic devices comprising the compounds, and the use of the compounds as semiconducting materials.

Convergent Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/Alkene Isomerization Sequence

A convergent synthetic method for the synthesis of fluorene derivatives has been developed by devising a rhodium-catalyzed stitching reaction/alkene isomerization sequence. The reactions proceed smoothly under mild conditions for a variety of substrate combinations, and extended π-conjugation systems are also readily accessible by utilizing this synthetic method. Optical properties of the obtained fluorene derivatives have also been examined.

The Effect of Ring Expansion in Thienobenzo[ b]indacenodithiophene Polymers for Organic Field-Effect Transistors

A fused donor, thienobenzo[b]indacenodithiophene (TBIDT), was designed and synthesized using a novel acid-promoted cascade ring closure strategy, and then copolymerized with a benzothiadiazole (BT) monomer. The backbone of TBIDT is an expansion of the well-known indacenodithiophene (IDT) unit and was expected to enhance the charge carrier mobility by improving backbone planarity and facilitating short contacts between polymer chains. However, the optimized field-effect transistors demonstrated an average saturation hole mobility of 0.9 cm2 V-1 s-1, lower than the performance of IDT-BT (～1.5 cm2 V-1 s-1). Mobilities extracted from time-resolved microwave conductivity measurements were consistent with the trend in hole mobilities in organic field-effect transistor devices. Scanning tunneling microscopy measurements and computational modeling illustrated that TBIDT-BT exhibits a less ordered microstructure in comparison to IDT-BT. This reveals that a regular side-chain packing density, independent of conformational isomers, is critical to avoid local free volume due to irregular packing, which can host trapping impurities. DFT calculations indicated that TBIDT-BT, despite containing a larger, planar unit, showed less stabilization of planar backbone geometries in comparison to IDT-BT. This is due to the reduced electrostatic stabilizing interactions between the peripheral thiophene of the fused core and the BT unit, resulting in a reduction of the barrier to rotation around the single bond. These insights provide a greater understanding of the general structure-property relationships required for semiconducting polymer repeat units to ensure optimal backbone planarization, as illustrated with IDT-type units, guiding the design of novel semiconducting polymers with extended fused backbones for high-performance field-effect transistors.

Small isomeric push-pull chromophores based on thienothiophenes with tunable optical (non)linearities

Fourteen new D-π-A push-pull chromophores based on two isomeric thienothiophene donors and seven acceptors of various electronic natures have been designed and conveniently synthesized. In contrast to known thienothiophene push-pull molecules, the prepared small chromophores proved to be organic materials with easily tunable thermal, electrochemical and (non)linear optical properties. It has also been shown that small structural variation may result in significantly improved/varied fundamental properties. Very detailed structure-property relationships were elucidated within the systematically developed series of push-pull molecules, which may serve as a useful guide in designing new D-π-A molecules based on fused thiophene scaffolds.

Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling

A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

Organic semiconducting compounds, manufacturing method thereof, and organic electronics devices containing the same

The present invention relates to an organic semiconductor compound of an organic thin film transistor comprising a thiophene vinylene monomer into which a cyano substituent is introduced at the position 3; a method for producing the same; and an organic electronic device containing the same. The organic semiconductor compound of the present invention has low LUMO energy level, and high thermal stability and solubility, and exhibits excellent n-type electron transfer characteristics in an organic electronic device including the same, particularly an organic thin film transistor device.COPYRIGHT KIPO 2018

Enhanced electrochromic performances of Polythieno[3,2-b]thiophene with multicolor conversion via embedding EDOT segment

A heterocyclic oligomer, thieno[3,2-b]thiophene (TT) end-capped famous 3,4-ethylenedioxythiophene (EDOT) unit and their electrosynthesized polymer P(TT-EDOT-TT) have been facilely achieved. To in-depth understand the effects of structural modification on physico-chemical properties and electrochromic performances of monomers and/or polymers, the absorption spectroscopy, electrochemistry, micromorphology, and spectroelectrochemistry were systematically studied. In contrast to TT and EDOT, TT-EDOT-TT possessed extended π-conjugation and narrowed band gap in molecular level. Through carefully comparison with PTT, it has been found that the electrochromic performances of P(TT-EDOT-TT) film exhibited much higher optical contrast (69%, while 3% for PTT in the near-infrared region) and superior coloring efficiency (255.3 cm2 C?1, while 36.8 cm2 C?1 for PTT), and switching times (within 1 s, while more than 9 s for PTT). Notably, P(TT-EDOT-TT) film can achieve the mutual conversion between RGB primary colors (red–green–blue) under variable voltages, which hold quite promising for display applications.

A new alkyl substituted and method for the synthesis of polythiophene

The invention provides a method for replacing multi-thiophthene with beta-dialkyl in a synthesis formula I. The method comprises the following steps of: (f) reacting an intermediate in a formula 10 to obtain an intermediate in a formula 11; (g) reacting the intermediate in the formula 11 to obtain an intermediate in a formula 12; (h) reacting the intermediate in the formula 12 to obtain an intermediate in a formula 13; (i) reacting the intermediate in the formula 13 to obtain an intermediate in a formula 8; (j) reacting the intermediate in the formula 8 to obtain an intermediate in a formula 9; and (k) reacting the intermediate in the formula 9 to obtain a compound in a formula I. The invention further relates to the intermediate in the formula 9. The method disclosed by the invention is low in cost, simple in process, high in yield and low in pollution. The formulas 10, 11, 12, 13, 8 and 9 are shown in the description.

Synthesis, Fluorescence, and Two-Photon Absorption Properties of Push–Pull 5-Arylthieno[3,2-b]thiophene Derivatives

Three series of novel push–pull 5-arylthieno[3,2-b]thiophene derivatives functionalized with potent electron-withdrawing terminal moieties have been synthesized in moderate to excellent yields by Suzuki coupling followed by Knoevenagel condensation. These novel chromophores show intense absorption in the near-UV region through to the orange visible region, related to a strong intramolecular charge-transfer transition. By combining a strong donor and acceptor, large fluorescence quantum yields were achieved as well as large two-photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (as compared with the bithiophene unit), higher one- and two-photon brightness values have been achieved. As a result, several new fluorescent dyes showing enhanced brightness and tunable fluorescence (ranging from the blue to the NIR region) have been obtained that have potential for bioimaging applications.