(2,4,5-Trimethylthiophen-3-yl)boronic acid pinacol ester

Name: (2,4,5-Trimethylthiophen-3-yl)boronic acid pinacol ester 

Molecular Formula: C₁₃H₂₁BO₂S 

CAS#: 2064117-97-9 

SMILES: CC1=C(C)C(B2OC(C)(C)C(C)(C)O2)=C(C)S1 

MDL#: MFCD26404006 

Catalog#: T36115 

Molecular weight: 252.18 g/mol

Other names: 

• 4,4,5,5-Tetramethyl-2-(2,4,5-trimethylthiophen-3-yl)-1,3,2-dioxaborolane 

Fields of Interest: Organic Synthesis, Suzuki-Miyaura coupling reactions  

Background & Applications:  Sulfur-containing heterocycles like (2,4,5-Trimethylthiophen-3-yl)boronic acid pinacol ester are a crucial class of compounds in organic chemistry due to their diverse structures and wide-ranging applications in various fields such as medicinal chemistry, agrochemicals, and materials science. These heterocycles incorporate sulfur atoms into their ring structures, which can significantly influence the chemical properties and biological activities of the compounds.

The most common catalysts used in Suzuki coupling reactions are palladium based; however, palladium is expensive, rare, and its presence in APIs is limited to a very low ppm by stringent regulatory requirements. New discoveries are making it possible to replace palladium with other less toxic and more available transition metals such as cobalt when the boronic acid is used as its neopentyl ester.

Appearance: Clear liquid 

Purity: 98% 

Storage: Store @ 3-5 °C under inert atmosphere 

Solubility:  

• Soluble in organic solvents such as ethyl ether or dioxane

Literature:  

1. Kotha, S.; Khedkar, P. Design of Synthetic Strategies towards Sulfur Containing Scaffolds. Synthesis 2024. https://doi.org/10.1055/s-0043-1775393.