3,5-Di-tert-butylsalicylaldehyde CAS 37942-07-7

3,5-Di-tert-butylsalicylaldehyde, also known as 3,5-Di-tert-butyl-2-hydroxybenzaldehyde, is an organic intermediate, which can be prepared from 2, 4-di-tert-butylphenol through one-step reaction. It has been reported that it can be used to prepare dimethyl ethyl#enediamine tert-butylphenol and (S,S)-salenCo (II) catalyst.

3,5-Di-tert-butylsalicylaldehyde is used in the synthesis of Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose, chiral Schiff base ligand for an enantioselective copper-catalyzed addition of phenyl acetylene to imines, chiral oxazolidine ligand for the enantioselective addition of diethyl zinc to aldehydes and tin Schiff base complexes with histidine analogues. 

3,5-Di-tert-butylsalicylaldehyde is a salicylaldehyde derivative with antibacterial activity used in the preparation nickel complexes. 3,5-Di-tert-butylsalicylaldehyde is structurally related to 3,5-di-t-butylcatechol (DTCAT) but is not as potent an activator of rat skeletal muscle ryanodine receptor Ca2+ channel (RyRC).

❶ Steric Hindrance: 3,5-Di-tert-butylsalicylaldehyde contains two bulky tert-butyl groups attached to the phenolic ring. This steric hindrance restricts molecular interactions, making it challenging for other molecules or metal ions to access specific reactive sites.

❷ Antibacterial Activity: The compound exhibits antibacterial properties, which can be beneficial in various applications, such as antimicrobial coatings or additives in certain products.

❸ Coordination Chemistry: 3,5-Di-tert-butylsalicylaldehyde can serve as a ligand in coordination complexes with various metal ions. Its steric hindrance influences the geometry and stability of the resulting metal complexes.

❹ Chirality: Due to its steric configuration, 3,5-Di-tert-butylsalicylaldehyde can serve as a chiral building block for the synthesis of chiral catalysts and ligands. This property is significant in asymmetric catalysis and organic synthesis.

❺ Electronic and Photophysical Properties: The tert-butyl groups' presence can influence the electronic and photophysical properties of 3,5-Di-tert-butylsalicylaldehyde and its derived compounds, making them interesting for optoelectronic and materials research.

❻ Applications in Chemical Research: 3,5-Di-tert-butylsalicylaldehyde is widely used in chemical research and the development of new materials, particularly in the synthesis of complex organic molecules.

❼ Precursor in Nickel Complexes: The compound is often employed in the preparation of nickel complexes, which can have diverse applications in catalysis and materials science.

❽ Structural Similarity: While structurally related to 3,5-di-t-butylcatechol (DTCAT), 3,5-Di-tert-butylsalicylaldehyde does not possess the same potent activating properties of rat skeletal muscle ryanodine receptor Ca2+ channel (RyRC).