Tert-Butyl Mesylate (CAS 16427-41-1) is a valuable reagent in the field of organic chemistry, widely used as an intermediate in the synthesis of more complex molecules. For chemists and chemical engineers, a thorough understanding of its chemical properties, synthesis methods, and reactivity is essential for effective utilization. This technical overview aims to provide detailed insights into this important compound.

With the molecular formula C5H12O3S and a molecular weight of 152.21 g/mol, Tert-Butyl Mesylate is typically presented as a liquid. Its chemical structure features a tert-butyl group attached to the methanesulfonate ester. This structure imbues it with specific reactivity, making it a useful methylsulfonating agent. The presence of the bulky tert-butyl group can also influence reaction stereochemistry and regioselectivity, offering advantages in certain synthetic routes.

Synthesis Pathways for Tert-Butyl Mesylate

The common synthesis of Tert-Butyl Mesylate involves the reaction between methanesulfonyl chloride and tert-butanol. This esterification reaction typically proceeds under basic conditions, often utilizing a tertiary amine base such as triethylamine or pyridine to scavenge the hydrochloric acid byproduct. The reaction is generally carried out in an inert solvent at controlled temperatures to maximize yield and purity.

Key Chemical Properties and Reactivity

  • Methylsulfonating Agent: The methanesulfonate group (-OSO2CH3) is a good leaving group, making Tert-Butyl Mesylate an effective agent for transferring this group to nucleophiles. This is particularly useful for converting alcohols into their corresponding mesylates, which are more reactive in subsequent nucleophilic substitution reactions.
  • Stability: Tert-Butyl Mesylate is generally stable when stored properly, usually under dry conditions at room temperature. However, like most esters, it can be susceptible to hydrolysis in the presence of strong acids or bases, especially at elevated temperatures.
  • Solubility: It is typically soluble in common organic solvents, which facilitates its use in various reaction media.

Applications in Organic Synthesis

Tert-Butyl Mesylate finds broad application in organic synthesis:

  • Formation of Alkyl Mesylates: It serves as a convenient reagent to convert tert-butyl alcohols into tert-butyl mesylates, which can then undergo further transformations.
  • Intermediate in Pharmaceutical Synthesis: Its structure makes it a valuable building block for creating complex pharmaceutical intermediates and active pharmaceutical ingredients (APIs).
  • Reagent in Specialty Chemical Production: It is utilized in the synthesis of various fine chemicals where the controlled introduction of a methanesulfonate ester is required.

For researchers and manufacturers looking to procure Tert-Butyl Mesylate, understanding its technical specifications and reactivity profile ensures optimal use in their synthetic endeavors. Engaging with reputable suppliers who can provide detailed product information and competitive pricing is a key step in acquiring this versatile chemical intermediate.