For chemists engaged in organic synthesis, a thorough understanding of their starting materials is fundamental to successful project outcomes. 1-Bromopinacolone (CAS 5469-26-1) is one such compound that offers significant synthetic potential. Its unique structural features dictate its reactivity and suitability for various chemical transformations. This article aims to provide a detailed look at its chemical properties, aiding researchers and procurement specialists in making informed decisions when planning their synthetic routes and sourcing strategies.

Molecular Structure and Key Properties

1-Bromopinacolone, also known by IUPAC name 1-bromo-3,3-dimethylbutan-2-one, possesses the molecular formula C6H11BrO and a molecular weight of approximately 179.06 g/mol. The molecule features a ketone functional group at the second carbon position and a bromine atom attached to the first carbon. The presence of a tert-butyl group (three methyl groups attached to a central carbon) imparts steric bulk around the ketone and the adjacent methylene group. This steric hindrance can influence reaction kinetics and regioselectivity in certain transformations.

The compound is typically described as a clear, pale yellow to yellow-brown liquid. Its melting point is reported to be around -10°C, indicating it remains liquid under standard laboratory conditions. The boiling point is in the range of 188-194°C. Crucially for many synthetic procedures, 1-Bromopinacolone is insoluble in water but soluble in common organic solvents, facilitating its integration into various reaction media. Its flash point is around 195°F (90.6°C), indicating moderate flammability.

Reactivity in Organic Transformations

The primary synthetic utility of 1-Bromopinacolone stems from the reactivity of the alpha-bromoketone moiety. The bromine atom is a good leaving group, making the adjacent methylene carbon susceptible to nucleophilic attack. This allows for a range of nucleophilic substitution reactions, where the bromine can be replaced by various nucleophiles such as amines, thiols, alkoxides, or carbanions. These reactions are foundational for building more complex molecular structures.

Furthermore, alpha-bromoketones are known to participate in reactions like the Favorskii rearrangement under basic conditions, leading to the formation of carboxylic acid derivatives. They can also be utilized in the synthesis of heterocycles, such as oxazoles and imidazoles, through condensation reactions with appropriate bifunctional nucleophiles. The tert-butyl group can influence the stereochemical outcome of reactions and provide a degree of stability to certain intermediates.

Procurement Considerations for Chemists

When considering 1-Bromopinacolone for your next synthesis, understanding these chemical properties will guide your choices. For example, if a reaction requires precise control over stereochemistry or is sensitive to steric bulk, the tert-butyl group might be a strategic advantage or consideration. When searching to buy 1-Bromopinacolone, it is vital to consult supplier specifications regarding purity and physical form. Reliable manufacturers will clearly list properties such as melting point, boiling point, density (around 1.331 g/mL at 25°C), and refractive index (n20/D 1.466). Engaging with knowledgeable suppliers and requesting detailed technical data sheets will ensure you procure the right material for your specific research and development objectives. For bulk quantities, inquiring about '1-Bromopinacolone price' from established manufacturers in China offers a cost-effective solution.

In summary, the chemical properties of 1-Bromopinacolone, particularly its alpha-bromoketone functionality and steric features, make it a valuable tool in the synthetic chemist's arsenal. A clear understanding of these properties, coupled with informed sourcing from reliable manufacturers, paves the way for successful and efficient chemical synthesis.