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

Base Information

• Chemical Name: 2,6-Di-tert-butyl-4-nitrophenol
• CAS No.: 728-40-5
• Molecular Formula: C14H21 N O3
• Molecular Weight: 251.326
• NSC Number: 81682
• UNII: R4V8VYQ7XL
• DSSTox Substance ID: DTXSID4021559
• Nikkaji Number: J6.951E
• Wikidata: Q63441408
• ChEMBL ID: CHEMBL224869
• Mol file: 728-40-5.mol

Synonyms:2,6-di-tert-butyl-4-nitrophenol;DBNP cpd

Chemical Property of 2,6-Di-tert-butyl-4-nitrophenol

Chemical Property:

• Vapor Pressure: 0.000423mmHg at 25°C
• Melting Point: 154-156℃
• Refractive Index: 1.5774 (estimate)
• Boiling Point: 307℃
• PKA: 7.17±0.40(Predicted)
• Flash Point: 118℃
• PSA: 66.05000
• Density: 1.078
• LogP: 4.41860
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 251.15214353
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

97% ^*data from raw suppliers

2,6-Di-tert-butyl-4-nitrophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)[N+](=O)[O-]
• General Description: DI-TERTBUTYLNITROPHENOL (DBNP) is a potent uncoupler of oxidative phosphorylation, characterized by its high lipophilicity and a pKa of 6.8, which enhances its passive diffusion across biological membranes at physiological pH. This property suggests it may be more effective than 2,4-dinitrophenol in disrupting ATP synthesis. DI-TERTBUTYLNITROPHENOL was synthesized from 2,6-di-tert-butylphenol via electrophilic aromatic substitution with NO2, achieving high purity and a 75% yield, though excessive NO2 leads to its decomposition. Analytical techniques confirmed its structural and thermal properties, supporting its potential use in toxicity studies.

Technology Process of 2,6-Di-tert-butyl-4-nitrophenol

There total 20 articles about 2,6-Di-tert-butyl-4-nitrophenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2,6-di-tert-butyl-anisole (1516-95-6) → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Guidance literature:

With sodium nitrite; In acetic acid;

DOI:10.1007/BF00963511

Reference yield: 94.0%

(2,6-Di-tert-butyl-phenyl)-methanol → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Guidance literature:

With sodium nitrite; In acetic acid;

DOI:10.1007/BF00963511

Reference yield: 94.0%

(2,6-Di-tert-butyl-phenyl)-dimethyl-amine → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Guidance literature:

With sodium nitrite; In acetic acid;

DOI:10.1007/BF00963511

upstream raw materials:

2,6-di-tert-butylphenol

Difluoroacetic acid

2,6-Di-tert-butyl-4-nitro-phenol anion

dichloro-acetic acid

Downstream raw materials:

C₂₂H₃₇NO₃

4-(methyl-aci-nitro)-2,6-di-t-butylcyclohexa-2,5-dienone

C₁₉H₃₁NO₄

C₁₆H₂₄N₄O₉

Refernces

10.1021/ja00846a035

The study investigates the impact of cationic micelles, specifically hexadecyltrimethylammonium bromide (CTABr), on the acidity of carbon acids and phenols, as well as the electronic and 'H nuclear magnetic resonance (NMR) spectral characteristics of nitro carbanions in micelles. The researchers found that CTABr micelles significantly enhance the acid dissociation of various carbon acids and phenols, with the effect being most pronounced for nitro carbanions. The study involved several chemicals, including 4-nitrophenylacetonitriles, 1-nitroindene, 4-nitrophenol, and 2,6-di-tert-butyl-4-nitrophenol, which were used to examine the changes in their acid dissociation constants (pKa values) in the presence of CTABr micelles. Additionally, the visible and 'H NMR spectra of these nitro carbanions were analyzed to understand the interactions between the carbanions and CTABr molecules. The results showed that CTABr micelles cause a red shift in the visible spectra of nitro carbanions and induce upfield shifts in the 'H NMR signals of the aromatic protons of the carbanions and the N+(CH3)3 protons of the surfactant, indicating tight interactions. The study concludes that the presence of CTABr micelles enhances the acidity of carbon acids and phenols by stabilizing the anionic form through tight association with the surfactant molecules, and the spectral changes observed are attributed to the unique interactions within the micelle environment rather than chemical reactions.