3140-92-9

Usage

Uses

Used in Organic Synthesis:
2,4-Dibromothiophene is used as an important intermediate in organic synthesis, playing a crucial role in the formation of various complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-Dibromothiophene is utilized as a key intermediate for the development of new drugs. Its chemical properties enable it to be incorporated into the structures of various medicinal compounds, potentially leading to the creation of novel therapeutic agents.
Used in Agrochemicals:
2,4-Dibromothiophene is also employed in the agrochemical sector as an intermediate for the synthesis of various pesticides and other agricultural chemicals. Its incorporation into these products can enhance their effectiveness in protecting crops and managing pests.
Used in Dye Industry:
In the dye industry, 2,4-Dibromothiophene serves as a vital intermediate for the production of different types of dyes. Its unique chemical structure contributes to the development of dyes with specific color properties and improved performance characteristics.
Overall, 2,4-Dibromothiophene is a versatile compound with applications across multiple industries, including organic synthesis, pharmaceuticals, agrochemicals, and the dye industry. Its chemical properties and structural features make it an essential component in the development of various products and materials.

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

Upstream product

• 3141-24-0 2,3,5-tribromothiophene 
• 925-90-6 ethylmagnesium bromide 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 696-62-8 para-iodoanisole 
• 3141-27-3 2,5-dibromothiophen 
• 100-52-7 benzaldehyde 

Downstream Products

• 16694-18-1 4-bromo-thiophene-2-carboxylic acid 
• 7311-68-4 3,5-dibromothiophene-2-carboxylic acid 
• 80775-52-6 1-(3,5-dibromo-[2]thienyl)-ethanone 
• 18791-75-8 4-Bromothiophen-2-aldehyde 
• 499769-92-5 (4-bromothiophen-2-yl)boronic acid 
• 73882-42-5 4-bromo-2-methoxythiophene 
• 78282-35-6 2-bromo-4-methoxythiophene 
• 117366-86-6 (3,5-Dibrom-2-thienyl)phenylmethanon 
• 153143-05-6 2,4-diethynylthiophene 
• 3172-56-3 3,3'-bithiophene 
• 105124-99-0 4-bromo-2,3'-bithienyl 
• 105124-97-8 3,2':4',3-terthiophen 
• 932-93-4 thiophene-2,4-dicarbaldehyde 
• 87310-65-4 4-bromo-2-(methylthio)thiophene 

Relevant academic research and scientific papers

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%.

Trapping of Transient Thienyllithiums Generated by Deprotonation of 2,3-or 2,5-Dibromothiophene in a Flow Microreactor

Selective trapping of (4,5-dibromo-2-thienyl)lithium, known to undergo halogen dance, was achieved in a flow microreactor. This transient thienyllithium, generated by mixing 2,3-dibromothiophene and lithium diisopropylamide at-78 °C for 1.6 seconds, react

One-Pot Halogen Dance/Negishi Coupling of Dibromothiophenes for Regiocontrolled Synthesis of Multiply Arylated Thiophenes

One-pot halogen dance/Negishi cross-coupling of readily available 2,5-dibromothiophenes is described. A lithium diisopropylamide (LDA)-mediated halogen dance reaction resulted in the formation of thermodynamically stable α-lithiodibromothiophenes, which w

Sterics versus electronics: Regioselective cross-coupling of polybrominated thiophenes

Methods for the regioselective cross-coupling of 2,3,5-tribromothiophene have been developed in which selective aryl-aryl coupling occurs at the 5-position with yields up to 63%. The difference in reactivity of the α- and β-positions then allows sequential regioselective couplings first at the 2-position, followed by the 3-position. Such regioselective cross-coupling allows unprecedented control in the generation of trifunctionalized thiophenes. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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.