40032-81-3

Basic information

• Product Name: 2-Chloro-3-bromomethylthiophene
• Synonyms: 2-CHLORO-3-BROMOMETHYLTHIOPHENE;3-bromomethyl-2-chlorothiophene;Thiophene, 3-(bromomethyl)-2-chloro-
• CAS NO: 40032-81-3
• Molecular Formula: C₅H₄BrClS
• Molecular Weight: 211.51
• Product Categories: Thiophene&Benzothiophene
• Mol File: 40032-81-3.mol

Chemical Properties

• Boiling Point: 225.062 °C at 760 mmHg
• Flash Point: 89.914 °C
• Appearance: /
• Density: 1.757 g/cm³
• Vapor Pressure: 0.132mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-Chloro-3-bromomethylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-bromomethylthiophene(40032-81-3)
• EPA Substance Registry System: 2-Chloro-3-bromomethylthiophene(40032-81-3)

Safety Data

• Hazardous Substances Data: 40032-81-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-bromomethylthiophene serves as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Chloro-3-bromomethylthiophene is utilized as a precursor in the production of pesticides and other crop protection agents. Its incorporation into these chemicals can enhance their effectiveness in controlling pests and diseases, thereby improving agricultural yields.
Used in Fine Chemicals Industry:
2-Chloro-3-bromomethylthiophene is also employed in the synthesis of fine chemicals, which are high-purity chemicals used in various applications such as fragrances, dyes, and specialty chemicals. Its versatility and reactivity make it a valuable component in creating complex and high-value chemical products.

InChI:InChI=1/C5H4BrClS/c6-3-4-1-2-8-5(4)7/h1-2H,3H2

Upstream product

• 14345-97-2 2-chloro-3-methylthiophene 
• 34241-39-9 azobisisobutyronitrile 

Relevant articles and documents

Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides

The first examples of efficient and general palladium-catalyzed intramolecular C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K 2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodology. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochemistry control.

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