37942-07-7

Basic information

• Product Name: 3,5-Di-tert-butylsalicylaldehyde
• Synonyms: 3,5-DI-TBUTYLSALICYLALDEHYDE;3,5-DI-TERT-BUTYL-2-HYDROXYBENZALDEHYDE;3,5-DI-T-BUTYL-2-HYDROXYBENZALDEHYDE;3,5-DI-TERT-BUTYLSALICYLALDEHYDE;3,5-bis(1,1-dimethylethyl)-2-hydroxy-benzaldehyde;BENZALDEHYDE, 3,5-BIS(1,1-DIMETHYLETHYL)-2-HYDROXY-;3,5-di-tert-Butyl Salicylaldehtde;Ditert-butyl-2-hydroxybenzaldehyde
• CAS NO: 37942-07-7
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33
• EINECS: -0
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Building Blocks;C13-C60;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Achiral Oxygen
• Mol File: 37942-07-7.mol
• Article Data: 60

Chemical Properties

• Melting Point: 59-61 °C(lit.)
• Boiling Point: 277.6 °C at 760 mmHg
• Flash Point: 116.1 °C
• Appearance: straw yellow to white crystal /powder
• Density: 1.006 g/cm³
• Vapor Pressure: 0.00266mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO and methanol.
• PKA: 9.78±0.23(Predicted)
• Sensitive: Air Sensitive
• BRN: 1877810
• CAS DataBase Reference: 3,5-Di-tert-butylsalicylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Di-tert-butylsalicylaldehyde(37942-07-7)
• EPA Substance Registry System: 3,5-Di-tert-butylsalicylaldehyde(37942-07-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 37942-07-7(Hazardous Substances Data)

Usage

Description

3,5-Di-tert-butylsalicylaldehyde is a salicylaldehyde derivative characterized by its white to yellow powder, chunk, or crystalline powder appearance. It is structurally related to 3,5-di-t-butylcatechol (DTCAT) and exhibits antibacterial activity. 3,5-Di-tert-butylsalicylaldehyde is also known for its use in the preparation of nickel complexes and its involvement in various chemical reactions, such as condensation reactions to yield Schiff base ligands.

Uses

Used in Chemical Synthesis:
3,5-Di-tert-butylsalicylaldehyde is used as a key compound in the synthesis of various complexes and ligands, including Mn(III)-salen complex, chiral Schiff base ligand for 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.
Used in Antibacterial Applications:
Due to its antibacterial activity, 3,5-Di-tert-butylsalicylaldehyde is utilized in the development of nickel complexes, which can be applied in various industries for their antimicrobial properties.
Used in Pharmaceutical Industry:
3,5-Di-tert-butylsalicylaldehyde is used as an intermediate in the synthesis of pharmaceutical compounds, particularly those involving the creation of Schiff base ligands and other complex molecules with potential therapeutic applications.
Used in Material Science:
3,5-Di-tert-butylsalicylaldehyde is also employed in material science for the development of novel complexes with potential applications in catalysis and other advanced material technologies.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 1939, 1994 DOI: 10.1021/jo00086a062Tetrahedron, 46, p. 793, 1990 DOI: 10.1016/S0040-4020(01)81362-4Tetrahedron Letters, 13, p. 4205, 1972 DOI: 10.1016/S0040-4039(01)94276-5

InChI:InChI=1/C15H22O2/c1-14(2,3)11-7-10(9-16)13(17)12(8-11)15(4,5)6/h7-9,17H,1-6H3

Upstream product

• 16373-02-7 2,4-di-tert-butyl-6-hydroxymethylphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 100-97-0 hexamethylenetetramine 
• 102519-99-3 2,4-Di-tert-butyl-6-(2-methyl-propenyl)-phenol 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 1428241-63-7 2,4-ditert-butyl-6-{4-[2-(6,8-ditert-butyl-4H-benzo[e][1,3]oxazin-3-yl)-ethyl]piperazin-1-ylmethyl}phenol 
• 75-05-8 acetonitrile 
• 188713-26-0 2,4-di-tert-butyl-6-([(2-dimethylaminoethyl)-(2-hydroxybenzyl)-amino]-methyl)-phenol 
• 354160-03-5 6,6′-(2-(pyridin-2-yl)ethylazanediyl)bis(methylene)bis(2,4-ditert-butylphenol) 
• 188713-27-1 N,N-bis(3,5-di-t-butyl-2-hydroxybenzyl)-N',N'-dimethylethylenediamine 
• 615553-86-1 (3,5-di-tert-butyl-2-hydroxyphenyl)bis(3,5-dimethyl-pyrazolyl)methane 
• 50-00-0 formaldehyd 
• 2934-05-6 2,4-diisopropylphenol 
• 32857-07-1 2,4-di-tert-butyl-6-(1,1-dimethylaminomethyl)phenol 

Downstream Products

• 103627-63-0 3-[1-(3,5-Di-tert-butyl-2-hydroxy-phenyl)-meth-(Z)-ylidene]-dihydro-furan-2-one 
• 155052-31-6 2,4-di-tert-butyl-6-({[(1S)-1-(hydroxymethyl)-2-methylpropyl]imino}methyl)phenol 
• 153034-24-3 3,5-di-tert-butyl-2-(propen-3-yloxy)benzaldehyde 
• 171775-14-7 (+/-)-3,5-di(tert-butyl)-2-hydroxy-α-methylbenzenemethanol 
• 38946-25-7 N-(3,5-di-t-butyl-2-hydroxybenzyl)-N',N'-dimethylenediamine 
• 214976-78-0 ((1S,2S)-(-)-1,2-diphenylethanediyl)bis(nitrilomethylidyne)bis(2,4-di-tert-butyl)phenol 
• 143560-44-5 2-(bis(2-hydroxy-3,5-di-tert-butylphenyl)methyl)-4,6-di-tert-butylphenol 

Relevant articles and documents

The solid-phase catalytic oxydation of 2-hydroxy-3,5-di-tert-butylbenzyl alcohol

The solid-phase catalytic oxidation in the 2-hydroxy-3,5-di-tert-butylbenzyl alcohol-MnO2-NaOH system to yield 2-hydroxy-3,5-di-tert-butylbenzaldehyde was carried out.Gaseous oxygen participates in the regeneration of the active form of the oxidant. - Key words: oxidation, benzyl alcohol, salicylic aldehyde, catalysis, synthesis, solid phase, liquid phase.

Optical and electrochemical properties of hydrogen-bonded phenol-pyrrolidino[60]fullerenes

We report the photophysical and electrochemical properties of phenol-pyrrolidino[60]fullerenes 1 and 2, in which the phenol hydroxyl group is ortho and para to the pyrrolidino group, respectively, as well as those of a phenyl-pyrrolidino[60]fullerene model compound, 3. For the ortho analog 1, the presence of an intramolecular hydrogen bond is supported by 1H NMR and FTIR characterization. The redox potential of the phenoxyl radical-phenol couple in this architecture is 240 mV lower than that observed in the associated para compound 2. Further, the C60 excited-state lifetime of the hydrogen-bonded compound 1 in benzonitrile is 260 ps, while the corresponding lifetime for 2 is identical to that of the model compound 3 at 1.34 ns. Addition of excess organic acid to a benzonitrile solution of 1 gives rise to a new species, 4, with an excited-state lifetime of 1.40 ns. In nonpolar aprotic solvents such as toluene, all three compounds have a C60 excited-state lifetime of a??1 ns. These results suggest that the presence of an intramolecular H-bond in 1 poises the potential of phenoxyl radical-phenol redox couple at a value that it is thermodynamically capable of reducing the photoexcited fullerene. This is not the case for the para analog 2 nor is it the case for the protonated species 4. This work illustrates that in addition to being used as light activated electron acceptors, pyrrolidino fullerenes are also capable of acting as built-in proton-accepting units that influence the potential of an attached donor when organized in an appropriate molecular design.

PROCESS FOR MAKING BIARYL-BRIDGED CYCLIC PEPTIDES

The invention provides a method of preparing a biaryl-bridged cyclic peptide compound of Formula (I), where R1, R2, R3, R4, R5, R8, R7, R8, R9, R10, R11, R12, n and m are as defined in the specification. The biaryl-bridged cyclic peptides of Formula (I) are used in the preparation of pharmaceutically active substances, such as, for example, arylomycin and arylomycin analogues.

Phosphasalalen Rare-Earth Complexes for the Polymerization of rac-Lactide and rac-β-Butyrolactone

A series of new phosphasalalen pro-ligands, analogues of salalen but with an iminophosphorane replacing the imine functionality, and their corresponding rare-earth alkoxide and siloxide complexes were synthesized. The multinuclear NMR spectra and X-ray diffraction analyses revealed that, for the tert-butoxide and ethoxide complexes, the resulting phosphasalalen rare-earth product was composed of a mononuclear alkoxide and a binuclear complex containing bridged alkoxo and hydroxo groups, while an analogous binuclear complex was isolated as the sole product for the siloxide complex. All the complexes could catalyze the heteroselective ring-opening polymerization (ROP) of rac-lactide (Pr up to 0.77) with high catalytic activities and a controlled polydispersity. Remarkably, the yttrium and lutetium phosphasalalen complexes could also efficiently catalyze the ROP of rac-β-butyrolactone to produce syndiotactic polymers (Pr up to 0.73) while their salalen analogues were inert, revealing the special effects of the iminophosphorane moiety. Detailed end-group analyses and kinetic investigations suggested that the alkoxo-hydroxo-bridged complexes maintained their binuclear structures in the polymerization.