2,6-Di-tert-butyl-4-nitrophenol

• CAS: 728-40-5
• Catalog Number: ACM728405
• Category: Main Products
• Molecular Weight: 251.32
• Molecular Formula: C14H21NO3
• Synonyms: 2,6-bis(1,1-Dimethylethyl)-4-nitrophenol
• Melting Point: 156 - 158 °C
• Appearance: Light Yellow to Yellow Solid

Case Study

2,6-Di-tert-butyl-4-nitrophenol as a Key Monomer Precursor for Low-Dielectric Tert-Butyl Polyimide Films in Microelectronics

Li, X., et al. (2024). Polymers, 16, 984.

2,6-Di-tert-butyl-4-nitrophenol acts as a critical starting material for synthesizing 4,4'-diamino-3,5-ditert butyl biphenyl ether, a bulky aromatic diamine monomer that introduces sterically demanding tert-butyl side chains into polyimide backbones to reduce dielectric constants for advanced microelectronic applications.
Experimental Protocol: 2,6-Di-tert-butyl-4-nitrophenol (0.50 g, 19.89 mmol) was reacted with p-chloronitrobenzene and potassium carbonate in methanol-dichloromethane at 80 degrees C for 24 hours to yield 4,4'-dinitro-3,5-ditert butyl biphenyl ether (80.5 percent yield). Catalytic hydrogenation with Pd/C and ammonium formate in 1,4-dioxane produced the diamine monomer (82.3 percent yield). Four distinct tert-butyl polyimide films (PI-1 through PI-4) were prepared via low-temperature polymerization with different aromatic dianhydride monomers.
Performance Evaluation: The optimized PI-4 film, synthesized using 3,3',4,4'-benzophenone tetracarboxylic anhydride, achieved the lowest dielectric constant of 2.90 at 1 MHz, substantially below the 3.6 value of a traditional non-tert-butyl polyimide control. PI-4 also exhibited a 5 percent weight loss temperature of 454 degrees C, tensile strength of 117.40 MPa, and a maximum water contact angle of 80.16 degrees, outperforming most reported low-dielectric polyimide films in the literature.

2,6-Di-tert-butyl-4-nitrophenol as a Sterically Demanding Pro-Ligand for Generating Unusual Copper(II) and Zinc(II) Nitronate Complexes with Hydrogen Atom Transfer Reactivity

Porter, T.R., et al. (2017). Dalton Transactions, 46, 2555-2564.

2,6-Di-tert-butyl-4-nitrophenol functions as a sterically encumbered pro-ligand that enforces an unusual nitronato-quinone binding mode upon deprotonation and coordination to bulky metal fragments, enabling stoichiometric hydrogen atom transfer chemistry at the resulting copper(II) complex.
Experimental Protocol: Treatment of a copper(II) trifluoroethoxide precursor with one equivalent of 2,6-di-tert-butyl-4-nitrophenol in benzene effected protolytic ligand exchange to yield the five-coordinate kappa²-nitronate complex. The zinc(II) analogue was obtained via reaction of a zinc triflate precursor with the phenol and DBU base in dichloromethane. The unsubstituted 4-nitrophenol analog formed a conventional O-bound phenoxide complex for structural comparison. X-band EPR spectroscopy and cyclic voltammetry were used to characterize electronic properties.
Performance Evaluation: The five-coordinate copper(II) nitronate complex reacted with one equivalent of TEMPO-H via hydrogen atom abstraction to quantitatively regenerate free 2,6-di-tert-butyl-4-nitrophenol and the copper(I) dimer, with TEMPO radical formed in near-quantitative yield. The balanced reaction stoichiometry established that the Gibbs free energy change for the net hydrogen atom transfer process is negative under experimental conditions. The same metal fragment bound unhindered 4-nitrophenol through the phenolate oxygen, confirming that steric clash between the tert-butyl substituents and the supporting hydrotris(3-tert-butyl-pyrazol-1-yl)borate ligand enforces the unusual nitronate coordination mode.

2,6-Di-tert-butyl-4-nitrophenol as a Lubricant Contaminant for Dermal Pharmacokinetic Assessment in Vascularized Human Skin Grafts

Pershing, L.K., et al. (2006). Journal of Applied Toxicology, 26, 402-409.

2,6-Di-tert-butyl-4-nitrophenol (DBNP), the nitrated metabolite of an antioxidant lubricant additive, serves as a model dermal contaminant for quantifying percutaneous uptake, disposition, and elimination kinetics in living vascularized human skin.
Experimental Protocol: A single topical dose of 75 micrograms DBNP in corn oil was applied to 1.33 cm² sites on human abdominal skin grafted onto athymic mice. Stratum corneum was harvested non-invasively using 20 sequential adhesive discs at 0.5, 1, 2, 4, 8, and 24 hours post-application. Punch biopsies were sectioned into epidermis (approximately 110 micrometers) and dermis (approximately 390 micrometers) compartments. DBNP concentrations in all skin layers were quantified by isocratic HPLC with UV detection at 325 nm. Pharmacokinetic parameters including C_max, T_max, AUC, and elimination half-life were calculated via non-compartmental analysis.
Performance Evaluation: The maximum DBNP concentration in stratum corneum was 1663 plus-minus 602 micrograms per cm³, approximately 30-fold and 300-fold greater than peak concentrations in epidermis and dermis, respectively. The time to maximum concentration was 1.0 hour in stratum corneum and dermis, and 0.5 hour in epidermis. The elimination half-life was 11 hours from stratum corneum and 9 hours from both viable epidermis and dermis. Over 24 hours, 77 percent of the applied dose remained on the skin surface, 15 percent was retained within the skin layers, and only 0.2 percent reached systemic circulation, establishing a steep concentration gradient.

Custom Q&A

What is the molecular formula of 2,6-Di-tert-butyl-4-nitrophenol?

The molecular formula is C14H21NO3.

What are the synonyms for 2,6-Di-tert-butyl-4-nitrophenol?

The synonyms are 2,6-ditert-butyl-4-nitrophenol, Bayer 4889, and Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitro.

What is the molecular weight of 2,6-Di-tert-butyl-4-nitrophenol?

The molecular weight is 251.32 g/mol.

When was 2,6-Di-tert-butyl-4-nitrophenol created?

It was created on March 26, 2005.

When was 2,6-Di-tert-butyl-4-nitrophenol last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 2,6-Di-tert-butyl-4-nitrophenol?

The IUPAC name is 2,6-ditert-butyl-4-nitrophenol.

What is the InChI of 2,6-Di-tert-butyl-4-nitrophenol?

The InChI is InChI=1S/C14H21NO3/c1-13(2,3)10-7-9(15(17)18)8-11(12(10)16)14(4,5)6/h7-8,16H,1-6H3.

What is the InChIKey of 2,6-Di-tert-butyl-4-nitrophenol?

The InChIKey is FCGKUUOTWLWJHE-UHFFFAOYSA-N.

What is the CAS number of 2,6-Di-tert-butyl-4-nitrophenol?

The CAS number is 728-40-5.

What is the XLogP3-AA value of 2,6-Di-tert-butyl-4-nitrophenol?

The XLogP3-AA value is 4.7.