25373-20-0

Basic information

• Product Name: 3,4-Dibromothiophene-2,5-dicarboxaldehyde
• Synonyms: 3,4-Dibromothiophene-2,5-dicarboxaldehyde;3,4-Dibromo-2,5-dicarboxaldehyde;3,4-Dibromo-2,5-thiophenedicarboxaldehyde
• CAS NO: 25373-20-0
• Molecular Formula: C₆H₂Br₂O₂S
• Molecular Weight: 297.95
• Product Categories: Thiophen;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 25373-20-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 227 °C
• Boiling Point: 376.3°C at 760 mmHg
• Flash Point: 181.4°C
• Appearance: /
• Density: 2.213g/cm³
• Vapor Pressure: 7.34E-06mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4-Dibromothiophene-2,5-dicarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dibromothiophene-2,5-dicarboxaldehyde(25373-20-0)
• EPA Substance Registry System: 3,4-Dibromothiophene-2,5-dicarboxaldehyde(25373-20-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 25373-20-0(Hazardous Substances Data)

Usage

General Description

3,4-Dibromothiophene-2,5-dicarboxaldehyde is a chemical compound with the molecular formula C8H4Br2O2S. It is a heterocyclic organic compound containing a thiophene ring with two bromine atoms and two aldehyde groups. 3,4-Dibromothiophene-2,5-dicarboxaldehyde is used in the synthesis of various pharmaceuticals, agrochemicals, and materials. It possesses unique properties that make it useful for its application in organic synthesis and as a building block in the production of complex molecules. 3,4-Dibromothiophene-2,5-dicarboxaldehyde is also employed in the development of organic light emitting materials, polymers, and organic electronic devices due to its potential for optoelectronic applications. Additionally, it is utilized in the creation of fluorescent dyes and organic semiconductors, making it an important component in the field of organic chemistry and materials science.

InChI:InChI=1/C6H2Br2O2S/c7-5-3(1-9)11-4(2-10)6(5)8/h1-2H

Upstream product

• 3958-03-0 Tetrabromothiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 2591-86-8 N-Formylpiperidine 
• 25373-19-7 3,4-dibromo-2,5-bis(dibromomethyl)thiophene 

Downstream Products

• 3141-26-2 3,4-dibromothiophene 
• 38319-52-7 (3,4-dibromo-thiophen-2-yl)-methanol 
• 64-18-6 formic acid 
• 7311-66-2 3,4-dibromo-2-thiophenecarboxylic acid 
• 854626-59-8 3,4-dibromo-thiophene-2-carboxylic acid-(3,4-dibromo-[2]thienylmethyl ester) 
• 502764-53-6 dithieno[3,2-b;20,30-d]-thiophene-2,6-dicarboxylic acid 
• 1425018-27-4 C₇₀H₅₆Br₂N₄S₃ 
• 67061-69-2 2,6-dibromodithieno[3,2-b:2',3'-d]thiophene 

Relevant articles and documents

Improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and derivatives for cross coupling

An improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and its 2,6- and 3,5-dibromo derivatives has been devised; Stille cross coupling of 2,5-(bistrimethylstannyl)-DTT afforded the oligomer 12.

Effect of the π-linker on the performance of organic photovoltaic devices based on push-pull D-π-A molecules

Two push-pull D-π-A molecules, 3T and DTT as donor materials, were synthesized and characterized for solution-processed bulk heterojunction (BHJ) organic photovoltaic (OPV) devices. The π-linker plays a vital role not only in electrochemical and thermal p

Efficient Synthesis of Bis(dibromomethyl)arenes as Important Precursors of Synthetically Useful Dialdehydes

This work presents an efficient synthesis of bis(dibromomethyl)benzenes and a bis(dibromomethyl)thiophene as precursors of aromatic dialdehydes by bromination of dimethyl-substituted arenes under various reaction conditions (yields up to 99%). Several new variants of this reaction, including the use of N-bromosuccinimide (NBS) and bromine, and various solvents to replace carbon tetrachloride, benzene and carbon disulfide, were also tested. In the optimised protocols, the inconvenient solvents were replaced by 1,2-dichloroethane (DCE) and/or acetonitrile. In the DCE protocols, we reduced reaction times 24-32-fold, reduced the amount of NBS a fewfold and lowered power consumption relative to the literature protocols. The procedures also allowed elimination of long-lasting incandescent irradiation (100-500 W). The replacement of NBS by bromine led to a further reduction in the amount of brominating agent. The obtained bromo derivatives were efficiently converted into the corresponding dialdehydes (90-96%), which in turn are useful in materials chemistry.