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

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

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

• 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 
• 96-76-4 2,4-di-tert-Butylphenol 
• 1557174-82-9 3,5-di-tert-butyl-2-((4-methoxybenzyl)oxy)benzaldehyde 
• 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 
• 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 
• 108-95-2 phenol 
• 32857-07-1 2,4-di-tert-butyl-6-(1,1-dimethylaminomethyl)phenol 
• 864066-01-3 2,4-di-tert-butyl-6-(1-hydroxy-2-methylpropyl)phenol 
• 128203-42-9 N-methyl-2,3-dihydro-1H-6,8-bis(1,1-dimethylethyl)benz[1,2-e][1,3]oxazine 

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 
• 151433-25-9 (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 
• 864066-01-3 2,4-di-tert-butyl-6-(1-hydroxy-2-methylpropyl)phenol 
• 135616-40-9 (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 
• 40473-49-2 3,5-di-tert-butyl-2-hydroxydiphenylcarbinol 
• 153034-24-3 3,5-di-tert-butyl-2-(propen-3-yloxy)benzaldehyde 
• 153034-28-7 3,5-di-tert-butyl-2-[(prop-2-yn-1-yl)oxy]benzaldehyde 
• 143569-55-5 methyl(2-hydroxy-3,5-di-tert-butyl)benzylimine 
• 171775-14-7 (+/-)-3,5-di(tert-butyl)-2-hydroxy-α-methylbenzenemethanol 
• 173030-55-2 3,5-di-tert-butylacetylsalicylic aldehyde 
• 188713-27-1 N,N-bis(3,5-di-t-butyl-2-hydroxybenzyl)-N',N'-dimethylethylenediamine 
• 38946-25-7 N-(3,5-di-t-butyl-2-hydroxybenzyl)-N',N'-dimethylenediamine 

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.

Cobalt(II) phenoxy-imine complexes in radical polymerization of vinyl acetate: The interplay of catalytic chain transfer and controlled/living radical polymerization

A series of cobalt(II) phenoxy-imine complexes (CoII(FI)2) have been synthesized to mediate the radical polymerization of vinyl acetate (VAc) and methyl acrylate (MA) to evaluate the influence of chelating atoms and configuration to the control of polymerization. The VAc polymerizations showed the properties of controlled/living radical polymerization (C/LRP) with complexes 1a and 3a, but the catalytic chain transfer (CCT) behaviors with complexes 2a, 1b, 2b, and 3b. The control of VAc polymerization mediated by complex 1a could be improved by decreasing the reaction temperature to approach the molecular weights that not only linearly increased with conversions but also matched the theoretical values and relatively narrow molecular weight distributions. The catalytic chain transfer polymerizations (CCTP) mediated by complexes 2a, 1b, 2b, and 3b were characterized by Mayo plots and the polymer chain end double bonds were observed by 1H NMR spectra. The tendency toward C/LRP or CCTP in VAc polymerization mediated by CoII(FI)2 could be determined by the ligand structure. Cobalt complex coordinated by the ligand with more steric hindered and less electron-donating substituents favored the controlled/living radical polymerization. In contrast, the efficiency of CCT process could be enhanced by less steric hindered, more electron-donating ligands. The controlled/living radical polymerization of MA, however, could not be achieved by the mediation of these cobalt(II) phenoxy-imine complexes. Associated with the results of polymerization mediated by other cobalt complexes, this study implied that the configuration and spin state of cobalt complexes were more critical than the chelating atoms to the control behavior of radical polymerization.

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.

Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands

Six novel chiral rare-earth-metal complexes bearing the phenoxy-functionalized TsDPEN ligand H3L1 (H3L1 = N-((1R,2R)-2-((3,5-di-Tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide) were synthesized successfully and well characterized. The solid-state structures of four tetranuclear rare-earth-metal complexes [RE2L13]2 (RE = Nd (1), Sm (2), Eu (3), Gd (4)) and the dual-core yttrium complex Y2L13 (5) were determined by X-ray diffraction, respectively. The structure of lanthanum complex 6 was speculated by the 1H DOSY spectroscopy in THF-d8 together with DFT calculations. Complexes 1-5 were employed to catalyze the enantioselective hydroboration of ketones and α,β-unsaturated ketones using pinacolborane (HBpin) as a reductant, and complex 1 gave better outcomes in comparison to the others. The corresponding secondary alcohols were obtained in excellent yields and moderate ee values. The same results were also achieved using the combined catalyst system of the neodymium amide Nd[N(SiMe3)2]3 with the phenoxy-functionalized TsDPEN ligand H3L1 in a 1:1.5 molar ratio.

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.

Synthesis of 6-tert-octyl and 6,8-ditert-butyl coumarins, two coumarins of biological interest

In this study, the synthesis of new coumarins with aliphatic chains is discussed. The incorporation of the 6-tert-octyl and 6,8-ditert-butyl chains into a coumarin structure from alkylphenols, allows obtaining hydrophobic coumarins with good yields. These coumarins can be potential modulators of TRPV1 receptors. Synthesis and spectroscopic data of these new coumarins are analyzed.

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.

ALPHAvBETA1 INTEGRIN ANTAGONISTS

The present disclosure provides pharmaceutical agents, including those of the formula: (I) wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such pharmaceutical agents. Methods of using the pharmaceutical agents are also provided. The compounds may be used for the inhibition or antagonism of integrins ανβ1 and/or α5β1. In some embodiments, the compounds provided herein exhibit reduced inhibitory or antagonistic activity of integrins ανβ3, ανβ5, ανβ6, ανβ8, and/or αIIbβ3.

Mononuclear Salen-Sodium Ion Pairs as Catalysts for Isoselective Polymerization of rac-Lactide

A series of mononuclear salen-sodium anions, as the first examples, were synthesized with tetra-alkyl ammonium as a counterpart cation. These complexes are efficient catalysts for the isoselective ring-opening polymerization of rac-lactide; the molecular weights of polymers are under control and molecular weight distributions are narrow when five equivalents of BnOH is used as an initiator. The best isoselectivity value of Pm = 0.82 was achieved at -70 °C. The experimental results together with a density functional theory calculation show that a ligand-assisted activated monomer mechanism is more reasonable than an activated monomer mechanism for this system.

Cobalt(II)[salen]-Catalyzed Selective Aerobic Oxidative Cross-Coupling between Electron-Rich Phenols and 2-Naphthols

A selectivity-driven catalyst design approach was adopted to address chemoselectivity issues in the oxidative coupling of phenols. This approach was utilized for developing a Co(II)[salen]-catalyzed aerobic oxidative cross-coupling of phenols in a recyclable 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) solvent. The waste-free conditions offer a sustainable entry to nonsymmetric biphenols via a mechanistic scheme that involves coupling of a liberated phenoxyl radical with a ligated 2-naphthoxyl radical.