Potassium tert-butoxide CAS: 865-47-4
Catalog Number | XD94245 |
Product Name | Potassium tert-butoxide |
CAS | 865-47-4 |
Molecular Formula | C4H9KO |
Molecular Weight | 112.21 |
Storage Details | Ambient |
Product Specification
Appearance | White powder |
Assay | 99% min |
Potassium tert-butoxide (KOC(CH3)3), also known as potassium tert-butanolate, is a strong and versatile base commonly used in organic synthesis and chemical reactions. It is a white, crystalline solid that readily dissolves in polar solvents like alcohols and ethers.One of the primary uses of potassium tert-butoxide is as a base in organic chemistry reactions. It is often employed for deprotonation reactions, where it abstracts a proton (H+) from a molecule, resulting in the formation of a corresponding alkoxide ion. This deprotonation is useful in many organic transformations, such as the synthesis of alcohols, ethers, esters, and carboxylic acids.Potassium tert-butoxide is particularly useful in reactions that involve hindered or weakly acidic protons. Its steric bulkiness (due to the presence of bulky tert-butyl groups) provides it with a greater ability to deprotonate acidic compounds compared to smaller bases like sodium hydroxide or sodium methoxide. This makes it useful in reactions that involve sterically hindered substrates or weakly acidic hydrogen atoms.Another important application of potassium tert-butoxide is its role as a strong base in elimination reactions. It is commonly used in reactions like the E2 (elimination bimolecular) mechanism, where it facilitates the removal of a leaving group and the formation of a double bond. This is particularly useful in the formation of alkenes from alkyl halides or sulfonates through reactions like the dehydrohalogenation of alkyl halides.Potassium tert-butoxide also finds use as a catalyst in various chemical reactions. It can be used in the synthesis of ethers through Williamson ether synthesis, where it promotes the reaction between an alkoxide ion and an alkyl halide. Additionally, it can be employed in coupling reactions, such as the Suzuki-Miyaura coupling, where it helps in the formation of carbon-carbon bonds.Furthermore, potassium tert-butoxide has been used for various other functional group transformations, including nucleophilic substitutions, rearrangements, and condensations. Its strong basicity and nucleophilic nature make it a valuable reagent in a wide range of organic transformations.Overall, potassium tert-butoxide is a versatile base and catalyst that finds widespread use in organic synthesis. Its strong basicity and steric bulkiness make it particularly useful in reactions involving hindered protons or sterically demanding substrates. Its applications in deprotonations, eliminations, and coupling reactions contribute to its importance in the field of organic chemistry.