3,5-Di-tert-butylsalicylaldehyde

3,5-Di-tert-butylsalicylaldehyde is white to yellow powder or chunks or crystal or crystalline powder

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).

3,5-Di-tert-butyl-2-hydroxybenzaldehyde 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. It has antibacterial activity and is used in the preparation nickel complexes. It 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).

3,5-Di-tert-butyl-2-hydroxybenzaldehyde was 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 phenylacetylene to imines
• chiral oxazolidine ligand for the enantioselective addition of diethylzinc to aldehydes
• tin Schiff base complexes with histidine analogues

ChEBI: 3,5-di-tert-butyl-2-hydroxybenzaldehyde is a hydroxybenzaldehyde.

The Journal of Organic Chemistry, 59, p. 1939, 1994 DOI: 10.1021/jo00086a062
Tetrahedron, 46, p. 793, 1990 DOI: 10.1016/S0040-4020(01)81362-4
Tetrahedron Letters, 13, p. 4205, 1972 DOI: 10.1016/S0040-4039(01)94276-5

3,5-Di-tert-butyl-2-hydroxybenzaldehyde undergoes condensation reaction with

• methyl-2-{N-(2′-aminoethane)}-amino-1-cyclopentenedithiocarboxylate to yield Schiff base ligand
• N,N-diethyl-2-methyl-1,4-phenylenediamine during the synthesis of copper(II) and cobalt(II) complexes of salicylaldimine

500mL cigar-shaped bottle was added 2,4-di-tert-butylphenol 50mmol, paraformaldehyde 500mmol, sodium hydroxide 150mmol, triethylamine 100mmol, tetrahydrofuran 100mL, 90 C heating reflux stirring reaction, TLC tracking the reaction process, the reaction was completed and reduced to room temperature. Hydrochloric acid was added to the reaction solution, stirring, until the reaction solution was clarified, layered, the aqueous phase was extracted with ethyl acetate, the organic phases were combined and washed with saturated brine, dried with anhydrous sodium sulfate, filtered, the solvent was spun off, and purified by column chromatography (n-hexane:ethyl acetate = 30:1) to obtain the product 10.56 g, yield 90.16%.