155954-63-5

Basic information

• Product Name: 4-Bromo-2-hexylthiophene
• Synonyms: 4-BROMO-2-HEXYLTHIOPHENE
• CAS NO: 155954-63-5
• Molecular Formula: C10H15BrS
• Molecular Weight: 247.2
• Mol File: 155954-63-5.mol

Chemical Properties

• Boiling Point: 276.1 °C at 760 mmHg
• Flash Point: 120.8 °C
• Appearance: Colorless liquid
• Density: 1.274 g/cm³
• Vapor Pressure: 0.00822mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 4-Bromo-2-hexylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-hexylthiophene(155954-63-5)
• EPA Substance Registry System: 4-Bromo-2-hexylthiophene(155954-63-5)

Safety Data

• Hazardous Substances Data: 155954-63-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
4-Bromo-2-hexylthiophene is used as a key component in the synthesis of organic electronic materials for its electronic properties. It is particularly utilized in the development of organic field-effect transistors and organic photovoltaic devices, contributing to their performance and efficiency.
Used in Organic Chemistry Research:
4-Bromo-2-hexylthiophene serves as a building block for the synthesis of more complex organic molecules in the field of organic chemistry. Its unique chemical structure and properties make it an essential component for creating innovative compounds and advancing scientific understanding in organic chemistry.

InChI:InChI=1/C10H15BrS/c1-2-3-4-5-6-10-7-9(11)8-12-10/h7-8H,2-6H2,1H3

Upstream product

• 155954-62-4 2-(n-Hex-1-enyl)-4-bromo thiophene 
• 18791-75-8 4-Bromothiophen-2-aldehyde 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 211737-28-9 2-bromo-5-hexylthiophene 
• 3140-92-9 2,4-dibromothiophene 
• 638-45-9 1-Iodohexane 
• 18794-77-9 2-hexylthiophene 
• 111-25-1 1-bromo-hexane 

Relevant articles and documents

Cata-Condensed Heteroannulated Coronenes via Selective Bromination of Diarenoperylenes as the Key Step

A facile three-step synthetic route to heteroannulated extended coronenes via a selective bromination of diarenoperylenes as the key step is presented. The heteroannulated coronenes were characterized by X-ray crystallography and by photophysical and electrochemical means.

Regiocontrolled Halogen Dance of Bromothiophenes and Bromofurans

The LDA (lithium diisopropylamide)-promoted regiocontrolled halogen dance of α-bromothiophenes and α-bromofurans is described. Bromothiophenes bearing a diethyl acetal moiety undergo selective deprotonation at the β-position adjacent to the bromo group. In contrast, oxazoline, ester, and amide groups act as directing groups in the initial lithiation step to generate a carbanion at the β-position neighboring the directing group to exclusively give the other regioisomer. These results can be applied to the regiocontrolled halogen dance of bromofuran derivatives.

5-Hexylthiophene-fused porphyrazines: New soluble phthalocyanines for solution-processed organic electronic devices

5-Hexylthiophene-fused porphyrazines were designed and synthesized as novel soluble phthalocyanine derivatives. Single-crystal X-ray structural analyses indicated that they have a well-ordered structure in the solid state in spite of the existence of diso

A containing oxygen race element and five fused ring conjugated molecule with the synthetic method of derivative thereof and use

The invention relates to an oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and a purpose thereof. A structure of the oxygen family element-containing penta-condensed ring conjugated molecule is shown as follows, and a structure of the derivative of the oxygen family element-containing penta-condensed ring conjugated molecule is shown as follows.

Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes

Over the past 20 years, ruthenium(II)-based dyes have played a pivotal role in turning dye-sensitized solar cells (DSCs) into a mature technology for the third generation of photovoltaics. However, the classic I3-/I- redox couple limits the performance and application of this technique. Simply replacing the iodine-based redox couple by new types like cobalt(3+/2+) complexes was not successful because of the poor compatibility between the ruthenium(II) sensitizer and the cobalt redox species. To address this problem and achieve higher power conversion efficiencies (PCEs), we introduce here six new cyclometalated ruthenium(II)-based dyes developed through ligand engineering. We tested DSCs employing these ruthenium(II) complexes and achieved PCEs of up to 9.4% using cobalt(3+/2+)-based electrolytes, which is the record efficiency to date featuring a ruthenium-based dye. In view of the complicated liquid DSC system, the disagreement found between different characterizations enlightens us about the importance of the sensitizer loading on TiO2, which is a subtle but equally important factor in the electronic properties of the sensitizers.

METHOD OF PRODUCING DITHIENOBENZO DITHIOPHENE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a simple and efficient production method for a dithienobenzo dithiophene derivative that can give high carrier mobility and makes it possible to form an organic semiconductor layer easily and efficiently. SOLUTION: A dithi

PRODUCTION METHOD OF DITHIENOBENZOTHIOPHENE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a production method of dithienobenzothiophene derivatives. SOLUTION: A production method of dithienobenzothiophene derivatives includes a step of reacting 2-bromo-5-alkylthiophene compound with lithium diisopropylamide to produce 3-bromo-5-alkylthiophene compound, monolithiating with a lithiating agent and reacting with sulfur and then with an oxidant to produce a disulfide compound, a step of subjecting 1,2,4,5-tetrahalobenzene dimetallation with a metallation agent and reacting with the disulfide compound to produce 1,4-bis(2-alkylthiophene-4-thioyl)-2,5-halobenzene and a step of tetralithiating with a lithiating agent and subjecting the resultant product to intramolecular cyclization with an oxidant to produce a compound of formula (1). In formula (1), R1 is H, a 1-20C alkyl group, a 3-10C cycloalkyl group, a 6-14C aryl group, a cycloheteroalkyl group of a 3- to 12-membered ring, etc. COPYRIGHT: (C)2016,JPOandINPIT

End-capping of conjugated thiophene-benzene aromatic systems

The synthesis of end-capped thieno[3,2-f:4,5-f′]bis[1]benzothiophene was achieved from thiophene and 2,5-thiophenedicarboxaldehyde. Specifically, hexyl and dodecyl end-capping groups conferred reversible redox behavior as evidenced by cyclic voltammetry with oxidation potentials of 0.73 V versus Fc/Fc+ couple. An extensive spectrophotometric analysis is reported.

NOVEL PORPHYRAZINE DERIVATIVE AND INTERMEDIATE THEREOF, METHOD FOR PRODUCTION OF NOVEL PORPHYRAZINE DERIVATIVE AND INTERMEDIATE THEREOF, AND USE OF PORPHYRAZINE DERIVATIVE

A porphyrazine derivative in which porphyrazine forms a condensed ring with thiophene and a skeleton of the thiophene has a functional group such as an alkyl group at position 2 has a high solubility in an organic solvent and exhibits a high crystallinity. Therefore, the porphyrazine derivative is suitably used in crystalline thin-film formation using a solution process. This provides a novel porphyrazine derivative and an intermediate thereof, which porphyrazine derivative has a high solubility in an organic solvent and is excellent in molecular orientation, a method for production of the porphyrazine derivative and the intermediate, and use of the porphyrazine derivative and the intermediate.

5-Substituted 3-thiophenesulfonamides as carbonic anhydrase inhibitors

A series of 5-substituted 3-thiophenesulfonamides was prepared from 4-bromo-2-thiophene carboxaldehyde. Several of these compounds inhibited carbonic anhydrase II in vitro at concentrations of less than 10 nM. In the ex vivo assay, these compounds have inhibitory values in the 25-81% range. Additionally, none of these compounds exhibit sensitization potential as determined by in vitro measurement of cysteine reactivity.