20039-94-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,4-Di(tert-butyl)-6-nitrophenol is utilized as an intermediate in the synthesis of a range of pharmaceuticals and agrochemicals. Its chemical structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a reagent, 2,4-di(tert-butyl)-6-nitrophenol plays a crucial role in organic synthesis, facilitating the formation of various organic compounds through its reactive functional groups.
Used in Polymer Production:
In the polymer industry, 2,4-di(tert-butyl)-6-nitrophenol serves as a stabilizer, enhancing the durability and performance of the final polymer products by preventing degradation and maintaining structural integrity.
Used in Medicine:
Due to its antibacterial and antifungal properties, 2,4-di(tert-butyl)-6-nitrophenol has potential applications in the medical field, where it could be used in the development of new antimicrobial agents to combat resistant infections.
Used in Agriculture:
Similarly, in agriculture, the compound's antimicrobial properties could be harnessed to develop new fungicides and bactericides, contributing to crop protection and yield enhancement.
It is essential to handle 2,4-di(tert-butyl)-6-nitrophenol with caution due to its potential health and environmental hazards, ensuring proper management and safety measures are in place during its use and disposal.

Upstream product

• 16373-02-7 2,4-di-tert-butyl-6-hydroxymethylphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 5470-11-1 hydroxylamine hydrochloride 
• 12030-88-5 potassium superoxide 
• 7722-84-1 dihydrogen peroxide 
• 162257-76-3 tetrakis(2,6-difluorophenyl)porphyrinate^(2-)iron(II) 
• 873055-54-0 carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester 
• 873055-55-1 carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester 
• 873055-56-2 carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester 
• 122422-38-2 2-(N,N-dimethylamino)-4,6-di-tert-butylphenol 
• 15515-54-5 2-methoxy-4,6-di-tert-butylphenol 

Downstream Products

• 94037-79-3 2,4-di-tert-butyl-4,6-dinitrocyclohexa-2,5-dienone 
• 55649-30-4 2,4,6,8-tetra-tert-butylphenoxazin-1-one 
• 1643-39-6 2-amino-4,6-di-tertbutylphenol 
• 99758-42-6 1,5-di-tert-butyl-2-methoxy-3-nitrobenzene 
• 328105-09-5 2,4-di-tert-butyl-6-{[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]amino}phenol 
• 1420-07-1 2-tert-butyl-4,6-dinitrophenol 

Relevant academic research and scientific papers

Conversion of {Fe(NO)2}10 dinitrosyl iron to nitrato iron(iii) species by molecular oxygen

A new {Fe(NO)2}10 dinitrosyl iron complex possessing a 2,9-dimethyl-1,10-phenanthroline ligand has been prepared. This complex exhibits dioxygenase activity, converting NO to nitrate (NO3 -) anions. During the o

Phenol Reduces Nitrite to NO at Copper(II): Role of a Proton-Responsive Outer Coordination Sphere in Phenol Oxidation

In the view of physiological significance, the transition-metal-mediated routes for nitrite (NO2-) to nitric oxide (NO) conversion and phenol oxidation are of prime importance. Probing the reactivity of substituted phenols toward the nitritocopper(II) cryptate complex [mC]Cu(κ2-O2N)(ClO4) (1a), this report illustrates NO release from nitrite at copper(II) following a proton-coupled electron transfer (PCET) pathway. Moreover, a different protonated state of 1a with a proton hosted in the outer coordination sphere, [mCH]Cu(κ2-O2N)(ClO4)2 (3), also reacts with substituted phenols via primary electron transfer from the phenol. Intriguingly, the alternative mechanism operative because of the presence of a proton at the remote site in 3 facilitates an unusual anaerobic pathway for phenol nitration.

Chromium(IV)-peroxo complex formation and its nitric oxide dioxygenase reactivity

The O2 and NO reactivity of a Cr(II) complex bearing a 12-membered tetraazamacrocyclic N-tetramethylated cyclam (TMC) ligand, [Cr II(12-TMC)(Cl)]+ (1), and the NO reactivity of its peroxo derivative, [CrIV(12-TM

A Peroxynitrite Dicopper Complex: Formation via Cu-NO and Cu-O2 Intermediates and Reactivity via O-O Cleavage Chemistry

A mixed-valent Cu(I)Cu(II) complex, [CuI,II2(UN-O-)]2+ (1), reacts with NO(g) at -80 °C to form [CuI,II2(UN-O-)(NO)]2+ (2), best described as a mixed-valent nitrosyl complex that has a ?(N-O) band at 1670 cm-1 in its infrared (IR) spectrum. Complex 2 undertakes a one-electron oxidation via the addition of O2(g) to generate a new intermediate, best described as a superoxide and nitrosyl adduct, [CuII2(UN-O-)(NO)(O2-)]2+ (3), based on its distinctively blue-shifted ?(N-O) band at 1853 cm-1. Over the course of 20 min at -80 °C, 3 is converted to the peroxynitrite (PN) complex [CuII2(UN-O-)(-OON=O)]2+ (4), which was characterized by low-temperature electrospray ionization mass spectrometry (ESI-MS) and IR spectroscopy; ?(N-O) absorptions at 1520 and 1640 cm-1 have been assigned as cis- and trans-conformers of the PN ligand in 4. Alternatively, the superoxide complex [CuII2(UN-O-)(O2?-)]2+ (5) is found to react with NO(g) to generate the same intermediate superoxide and nitrosyl adduct 3 (based on IR criteria), which likewise converts to the same PN complex 4. The O-O bond in 4 undergoes heterolysis in dichloromethane solvent and is postulated to produce nitronium ion, leading to ortho-nitration of 2,4-di-tert-butylphenol (DTBP). However, in 2-methyltetrahydrofuran as solvent, the O-O bond undergoes homolysis to generate ?NO2 (detected spectrophotometrically) and a putative higher-valent complex, [CuII,III2(UN-O-)(O2-)]2+, that abstracts a H-atom from DTBP to give [CuII2(UN-O-)(OH)]2+ and a phenoxyl radical. The latter may dimerize to form the bis-phenol observed experimentally or couple with the ?NO2 present, leading to o-phenol nitration.

Reactions of a chromium(III)-superoxo complex and nitric oxide that lead to the formation of chromium(IV)-oxo and chromium(III)-nitrito complexes

The reaction of an end-on Cr(III)-superoxo complex bearing a 14-membered tetraazamacrocyclic TMC ligand, [CrIII(14-TMC)(O2)(Cl)] +, with nitric oxide (NO) resulted in the generation of a stable Cr(IV)-oxo species, [CrIV(14-TMC)(O)(Cl)]+, via the formation of a Cr(III)-peroxynitrite intermediate and homolytic O-O bond cleavage of the peroxynitrite ligand. Evidence for the latter comes from electron paramagnetic resonance spectroscopy, computational chemistry and the observation of phenol nitration chemistry. The Cr(IV)-oxo complex does not react with nitrogen dioxide (NO2), but reacts with NO to afford a Cr(III)-nitrito complex, [CrIII(14-TMC)(NO2)(Cl)] +. The Cr(IV)-oxo and Cr(III)-nitrito complexes were also characterized spectroscopically and/or structurally.

Stable M(II)-Radicals and Nickel(III) Complexes of a Bis(phenol) N-Heterocyclic Carbene Chelated to Group 10 Metal Ions

The tetradentate ligand based on (1-imidazolium-3,5-ditert-butylphenol) units was prepared and chelated to group 10 metal ions (Ni(II), Pd(II), and Pt(II)), affording complexes 1, 2, and 3, respectively. The X-ray crystal structures of 1-3 show a square p

An isoelectronic NO dioxygenase reaction using a nonheme iron(iii)-peroxo complex and nitrosonium ion

Reaction of a nonheme iron(iii)-peroxo complex, [FeIII(14-TMC) (O2)]+, with NO+, a transformation which is essentially isoelectronic with that for nitric oxide dioxygenases [Fe(iii)(O2?-) +

REGIOCONTROLLED NITRATION OF DI(TERT-BUTYL)PHENOLS

The nitration of 2,4-di(tert-butyl)phenol and 2,6-di(tert-butyl)phenol is accoompanied by ooxidative processes, leading to products of the oxidative coupling of the starting di(tert-butyl)phenols.On the other hand, the corresponding nitrophenols are formed in quantitative yield in the substitutive nitration of 6-XCH2- and 4-XCH2-di(tert-butyl)phenols (X=OH, OR, NR2).

Phenol nitration induced by an {Fe(NO)2}10 dinitrosyl iron complex

Cellular dinitrosyl iron complexes (DNICs) have long been considered NO carriers. Although other physiological roles of DNICs have been postulated, their chemical functionality outside of NO transfer has not been demonstrated thus far. Here we report the unprecedented dioxygen reactivity of a N-bound {Fe(NO)2}10 DNIC, [Fe(TMEDA)(NO)2] (1). In the presence of O2, 1 becomes a nitrating agent that converts 2,4,-di-tert-butylphenol to 2,4-di-tert-butyl-6-nitrophenol via formation of a putative iron-peroxynitrite [Fe(TMEDA)(NO)(ONOO)] (2) that is stable below -80 C. Iron K-edge X-ray absorption spectroscopy on 2 supports a five-coordinated metal center with a bound peroxynitrite in a cyclic bidentate fashion. The peroxynitrite ligand of 2 readily decays at increased temperature or under illumination. These results suggest that DNICs could have multiple physiological or deleterious roles, including that of cellular nitrating agents.

Reaction of a Co(III)-Peroxo Complex and NO: Formation of a Putative Peroxynitrite Intermediate

A Co(II) complex, [Co(L)2]Cl2, 1 of the ligand L (L = bis(2-ethyl-4-methylimidazol-5-yl)methane) upon reaction with H2O2 in methanol solution at ?40 °C resulted in the formation of the corresponding Co(III)-peroxo complex [Co(L)2(O2)]+ (2). The addition of NO gas to the freshly generated solution of the complex 2 led to the formation of the Co(II)-nitrato complex 3 through the putative formation of a Co(II)-peroxynitrite intermediate, 2a. The intermediate 2a was found to mediate the nitration of the externally added phenol resembling the nitration of tyrosine in biological systems.