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Lithium Tri-tert-butoxyaluminum Hydride (LTBA): A Selective Reducing Agent

Lithium Tri-tert-butoxyaluminum Hydride (LTBA), identified by its Chemical Abstracts Service (CAS) number 17476-04-9, stands as a cornerstone reagent in modern organic synthesis. This versatile compound is primarily valued for its role as a highly selective reducing agent, a critical attribute in the precise construction of complex organic molecules across various industries. Unlike stronger, non-selective hydrides, LTBA offers unparalleled control, making it indispensable for specific transformations.


Chemically, LTBA possesses the molecular formula C12H28AlLiO3 and a molecular weight of approximately 254.27 g/mol. In its pure form, it typically appears as a white powder or chunks. Key physical properties include a melting point ranging from 300-319℃ (with decomposition) and a density of 0.942 g/mL at 25℃. It is known to react vigorously with water, underscoring the importance of anhydrous conditions during its handling and storage. LTBA is soluble in various organic solvents at low temperatures, such as tetrahydrofuran (THF) and diglyme, which are often used for its commercial presentation as a solution. For optimal stability and to maintain its high purity of 97% minimum, LTBA should be stored in a tightly closed container at a temperature of 2-8℃, ideally under an inert atmosphere like Argon to protect it from moisture and air.


The remarkable selectivity of LTBA is attributed to its unique steric bulk. The three large tert-butoxy groups attached to the aluminum center create a "fat suit" around the aluminum hydride, effectively modulating and slowing down its reactivity. This steric hindrance ensures that the hydride can only access less hindered functional groups, thus preventing over-reduction. Furthermore, having only one hydride to donate, in contrast to the four hydrides of lithium aluminum hydride (LiAlH4), allows for more controlled stoichiometry and a cleaner reaction profile, significantly simplifying reaction management and product purification.


LTBA's most significant application lies in the partial reduction of acid halides to aldehydes. This transformation is exceptionally valuable because aldehydes are highly reactive intermediates that are easily over-reduced to primary alcohols by less selective reducing agents. By using LTBA, synthetic chemists can convert carboxylic acids (after conversion to acid chlorides) directly into aldehydes in a single, controlled step. This avoids the need for a two-step process involving full reduction to an alcohol followed by an oxidation step, thereby increasing overall yield and efficiency. The mechanism typically involves a nucleophilic acyl substitution: hydride addition to the carbonyl, forming a tetrahedral intermediate, followed by the elimination of the halide leaving group to yield the aldehyde.


Beyond acid halides, LTBA also demonstrates utility in reducing aldehydes and ketones to their corresponding alcohols. However, it exhibits a notable lack of reactivity towards other common functional groups such as esters, lactones, epoxides, nitriles, and alkyl halides. This differentiated reactivity makes LTBA an indispensable tool when working with poly-functionalized molecules, allowing chemists to target specific carbonyl groups without affecting other sensitive functionalities within the same molecule. Its precision is vital in the synthesis of complex active pharmaceutical ingredients, fine fragrances, specialized pesticides, and high-performance dyes, where specific aldehyde or alcohol functionalities are required.


The consistent availability of high-quality Lithium Tri-tert-butoxyaluminum Hydride is crucial for advancing research and development in these critical areas. NINGBO INNO PHARMCHEM CO.,LTD. is a dedicated manufacturer and trusted supplier of this sophisticated reagent, upholding rigorous quality control standards to ensure exceptional purity and performance for every batch. We offer competitive price options and support seamless logistics for your global procurement needs. To buy Lithium Tri-tert-butoxyaluminum Hydride or to inquire about our comprehensive product range, please visit our website or contact our sales team. Your purchase of this selective reducing agent from NINGBO INNO PHARMCHEM CO.,LTD. guarantees a product engineered for success in your most demanding synthetic challenges.

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