In the intricate world of organic chemistry, certain molecules serve as foundational building blocks, enabling the synthesis of complex and valuable compounds. Tert-Butyl 5-Bromopentanoate, identified by CAS number 88987-42-2, is one such indispensable intermediate. Known for its specific structural features and reactivity, it finds widespread use across research and industrial applications, particularly within the pharmaceutical and agrochemical sectors.

Chemical Profile of Tert-Butyl 5-Bromopentanoate

Tert-Butyl 5-Bromopentanoate, also referred to as tert-butyl 5-bromovalerate or 5-bromopentanoic acid tert-butyl ester, is a chemical compound characterized by its distinct molecular structure. It features a five-carbon chain with a bromine atom at the alpha position relative to the ester, and a tert-butyl group protecting the carboxyl function. Its physical state is typically a liquid, appearing as colorless to light yellow. Key physical properties include a boiling point of approximately 93 °C at 1.6 Torr and a density around 1.223 g/cm³.

The compound's chemical reactivity stems from the presence of the alkyl bromide, which is susceptible to nucleophilic substitution reactions. This makes it an excellent alkylating agent. The tert-butyl ester group provides protection for the carboxylic acid, allowing for selective reactions elsewhere in the molecule, and can be removed under acidic conditions when needed.

Synthetic Pathways and Reactivity

The synthesis of Tert-Butyl 5-Bromopentanoate often involves the esterification of 5-bromovaleric acid. A common method described in literature involves reacting 5-bromovaleric acid with tert-butanol in the presence of a coupling agent like dicyclohexylcarbodiimide (DCC) and a catalyst such as 4-(dimethylamino)pyridine (DMAP). Alternative methods may utilize other dehydrating agents or catalysts to achieve the desired esterification. Yields are typically reported in the range of 60-70%, with purification often performed using silica gel column chromatography.

As a building block in organic synthesis, Tert-Butyl 5-Bromopentanoate participates in a variety of reactions:

  • Nucleophilic Substitution: The primary bromide can be displaced by nucleophiles (e.g., amines, thiols, alkoxides) to form new carbon-heteroatom bonds.
  • Grignard Reagent Formation: It can be converted into a Grignard reagent, which is a powerful tool for carbon-carbon bond formation.
  • Further Functionalization: The ester group can be hydrolyzed to the free acid or reduced to an alcohol, providing further synthetic avenues.

Procurement Considerations for Research & Industry

For research scientists and procurement managers, sourcing high-quality Tert-Butyl 5-Bromopentanoate is critical. When looking to buy this intermediate, consider partnering with reliable manufacturers and suppliers who can guarantee purity and consistency. Key factors include:

  • Purity Levels: Aim for products with 99% or higher purity to ensure predictable reaction outcomes.
  • Supplier Reliability: Choose manufacturers with a proven track record in fine chemical production, especially those in China offering competitive pricing.
  • Technical Documentation: Ensure availability of CAS details, MSDS, and CoAs.
  • Sample Availability: Requesting samples is recommended for preliminary testing.

Engaging with suppliers to obtain quotes for various quantities, from grams to kilograms, is standard practice. Understanding the lead times and shipping logistics is also important for project planning.

In conclusion, Tert-Butyl 5-Bromopentanoate (CAS 88987-42-2) is a cornerstone reagent in modern organic synthesis. Its versatile reactivity and utility in creating complex molecules make it an essential item for any chemical laboratory or manufacturing process. Identifying and partnering with reputable suppliers is key to unlocking its full potential.