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
• Article Data: 2

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

General Description

2-Chloro-3-bromomethylthiophene is a chemical compound with the molecular formula C5H4BrClS. It is a heterocyclic organic compound containing chlorine, bromine, and sulfur atoms. 2-Chloro-3-bromomethylthiophene is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It is also known for its strong odor and can be potentially harmful if inhaled or ingested. 2-Chloro-3-bromomethylthiophene is a highly reactive compound and must be handled with caution in laboratory settings.

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.