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Basic information

• Product Name: 2,6-Di-tert-butyl-4-nitrophenol
• Synonyms: DI-TERTBUTYLNITROPHENOL;2,6-Bis(1,1-dimethylethyl)-4-nitrophenol;B-28589;BAY-28589;Bayer-28589;ENT-25569;4-Nitro-2,6-bis-(1,1-dimethylethyl)phenol;4-Nitro-2,6-di-tert-butylphenol
• CAS NO: 728-40-5
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.33
• Mol File: 728-40-5.mol

Chemical Properties

• Melting Point: 154-156℃
• Boiling Point: 307℃
• Flash Point: 118℃
• Appearance: /
• Density: 1.078
• Vapor Pressure: 0.000423mmHg at 25°C
• Refractive Index: 1.5774 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.17±0.40(Predicted)
• CAS DataBase Reference: 2,6-Di-tert-butyl-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Di-tert-butyl-4-nitrophenol(728-40-5)
• EPA Substance Registry System: 2,6-Di-tert-butyl-4-nitrophenol(728-40-5)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 728-40-5(Hazardous Substances Data)

Usage

Uses

Used in Propellants and Explosives Industry:
DI-TERTBUTYLNITROPHENOL is used as a stabilizer for enhancing the shelf life of explosives and propellants. It inhibits the breakdown of these materials, ensuring their stability and safety over time.
Used in Fuel Industry:
As a fuel additive, DI-TERTBUTYLNITROPHENOL is utilized to improve the performance and efficiency of fuels, contributing to better combustion and reduced emissions.
Used in Pharmaceutical Industry:
In the production of certain pharmaceuticals, DI-TERTBUTYLNITROPHENOL serves as an essential component, playing a role in the synthesis of specific medications.

InChI:InChI=1/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

Synthetic route

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

Conditions	Yield
With sodium nitrite In acetic acid	94%

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

Conditions	Yield
With sodium nitrite In acetic acid	94%

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

Conditions	Yield
With sodium nitrite In acetic acid	94%

2,6-di-tert-butylphenol (128-39-2) → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
With aluminum(III) nitrate nonahydrate; oxalic acid at 20℃; for 0.5h; Grinding; neat (no solvent);	92%
With tert.-butylnitrite In tetrahydrofuran at 20℃; for 12h;	72%
With nitric acid In cyclohexane; acetic acid at 10 - 20℃; for 0.25h;	65%

2,6-di-tert-butylphenol (128-39-2) + Nitrogen dioxide (10102-44-0) → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
In hexane at 28℃; for 1h; Nitration;	75%

2,6-di-tert-butylphenol (128-39-2) → 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
With sodium nitrite In acetic acid	A 30% B 58%
With Nitrogen dioxide In methanol at 20℃; for 1h;

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
With nitric acid; sodium nitrite In tetrachloromethane Ambient temperature;	A 37% B 31%

2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide (105654-11-3) → 4-nitro-2,6-di-tert-butylphenol (728-40-5) + 2,4,5,5-tetramethyl-2-<2-(1-hydroxy-3,5-di-tert-butylcyclohexadien-2,5-onyl)-1-ethyl>-3-imidazoline 3-oxide (105654-17-9) + 1-nitroso-2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide + 1-nitroso-2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide

Conditions	Yield
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature; Yields of byproduct given;	A 7% B 18% C n/a D n/a
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature;	A 7% B 18% C n/a D n/a
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature; Yield given;	A 7% B 18% C n/a D n/a

Difluoroacetic acid (381-73-7) + 2,6-Di-tert-butyl-4-nitro-phenol anion (56577-75-4) → 4-nitro-2,6-di-tert-butylphenol (728-40-5) + 2,2-difluoroacetate (83193-04-8)

Conditions	Yield
In dimethyl sulfoxide at 20℃; Rate constant; Equilibrium constant;

dichloro-acetic acid (79-43-6) + 2,6-Di-tert-butyl-4-nitro-phenol anion (56577-75-4) → 4-nitro-2,6-di-tert-butylphenol (728-40-5) + 2,2-difluoroacetate (83193-04-8)

Conditions	Yield
In dimethyl sulfoxide at 20℃; Equilibrium constant; Rate constant;

2,6-di-tert-butylphenol (128-39-2) → 2-tert-butyl-4,6-dinitrophenol (1420-07-1) + 4-nitro-2,6-di-tert-butylphenol (728-40-5) + 2,6-di-tert-butyl-6-nitrocyclohexa-2,4-dienone + 2,6-di-tert-butyl-4-nitrocyclohexa-2,5-dienone (94037-77-1) + 2,6-di-tert-butyl-4,6-dinitrocyclohexa-2,4-dienone (94037-78-2)

Conditions	Yield
With nitric acid In acetic anhydride at -60 - 0℃; Product distribution; Mechanism; ratio of product depending on temperature and time, other solvents; also 2,4 and 3,5 substituted derivatives, other product;

N,N-dimethylbenzylammonium ion (54061-38-0) + 2,6-Di-tert-butyl-4-nitro-phenol anion (56577-75-4) → N,N'-dimethylbenzylamine (103-83-3) + 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
In dimethyl sulfoxide at 20℃; Equilibrium constant; Rate constant;

4-Nitro-2,6-di-tert-butyl-phenoxyl (10452-78-5) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 4-nitro-2,6-di-tert-butylphenol (728-40-5) + 2,6-di-tert-butyl-4-formyl-phenyloxyl (14446-91-4)

Conditions	Yield
In benzene at 21℃; relative equilibrium constants; other 2,6-di-tert-butylphenols and bicyclic phenols;

3,5-Di-tert-butyl-4-hydroxybenzoic acid (1421-49-4) → 4-nitro-2,6-di-tert-butylphenol (728-40-5)

Conditions	Yield
With nitric acid In acetic acid

Upstream product

• 128-39-2 2,6-di-tert-butylphenol 
• 381-73-7 Difluoroacetic acid 
• 56577-75-4 2,6-Di-tert-butyl-4-nitro-phenol anion 
• 79-43-6 dichloro-acetic acid 
• 1516-95-6 2,6-di-tert-butyl-anisole 
• 54061-38-0 N,N-dimethylbenzylammonium ion 
• 105654-11-3 2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide 
• 10452-78-5 4-Nitro-2,6-di-tert-butyl-phenoxyl 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 1421-49-4 3,5-Di-tert-butyl-4-hydroxybenzoic acid 
• 88-26-6 3,5-di-tert-butyl-4-hydroxybenzyl alcohol 
• 10102-44-0 Nitrogen dioxide 

Downstream Products

• 71671-13-1 C₂₄H₃₉NO₃ 
• 71671-15-3 C₂₀H₃₃NO₄ 
• 15052-30-9 4-(isopropyl-aci-nitro)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 71671-12-0 C₂₂H₃₇NO₃ 
• 75958-94-0 C₁₈H₂₉NO₄ 
• 72005-52-8 C₁₈H₂₉NO₄ 
• 71671-11-9 2-phenylethyl aci-nitronate 
• 4610-03-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenylimino)-2,5-cyclohexadien-1-one 
• 15052-27-4 4-(methyl-aci-nitro)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 15052-29-6 4-(ethyl-aci-nitro)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 71671-14-2 C₁₉H₃₁NO₄ 
• 54061-38-0 N,N-dimethylbenzylammonium ion 
• 56577-75-4 2,6-Di-tert-butyl-4-nitro-phenol anion 
• 75958-87-1 C₂₂H₃₇NO₃ 

Relevant articles and documents

Facile synthesis and physical and spectral characterization of 2,6-di-tert-butyl-4-nitrophenol (DBNP): a potentially powerful uncoupler of oxidative phosphorylation

The compound 2,6-di-tert-butyl-4-nitrophenol (DBNP), a potentially powerful uncoupler of ATP-generating oxidative phosphorylation, has been physically and spectroscopically characterized using X-ray crystallography, differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), GC-MS spectrometry, Fourier-transformed IR (FTIR) spectrophotometry, UV-VIS spectrophotometry, and FT (1)H- and (13)C-NMR spectroscopy. However, DBNP is not commercially available; therefore, it had to be synthesized in the laboratory prior to toxicity studies. The DBNP was prepared from 2,6-di-tert-butylphenol (DBP) precursor in hexane through an electrophilic aromatic substitution process using NO2. A collective yield of 75 percent was obtained by using two empirically determined end points that prevented the coprecipitation of reaction by-products and resulted in the formation of DBNP in high purity. Excessive amounts of NO2 in reaction mixtures resulted in the decomposition of preformed DBNP. With a pKa value of 6.8 and a higher degree of lipophilicity, DBNP may prove to be a stronger uncoupler of oxidative phosphorylation than 2,4-dinitrophenol (pKa=4.09) due to the expected enhancement of passive-diffusion kinetics across biological membranes at the physiological pH of 7.4. The present study is intended to provide analytical toxicologists, industrial hygiene monitors, and other professionals involved in chemical health and safety with a comprehensive source of basic information on the synthesis and analytical chemistry of DBNP.

Phenolic amine compound and preparation method and application thereof

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The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Highly efficient nitration of phenolic compounds using some nitrates and oxalic acid under solvent-free conditions

Nitrophenols can be obtained by direct nitration of phenols with some nitrates and oxalic acid at room temperature in moderate to high yields under solvent-free conditions. A small amount of water proved to be important in the initial period of the reaction.

Chemoselective nitration of phenols with iert-butyl nitrite in solution and on solid support

test-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononltro derivatives of phenolic substrates In the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nltrosyl Intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method Is compatible with tyroslne-containlng peptides on solid support In the synthesis of fluorogenic substrates for characterization of proteases.

TETRAHYDROISOQUINOLINE COMPOUND AND MEDICINAL USE THEREOF

The present invention provide a tetrahydroisoquinoline compound having a superior ACAT-inhibitory activity and/or anti-oxidation action, particularly, novel compound represented by the formula (I) (wherein each symbol is as described in the specification) and a pharmaceutically acceptable salt thereof.

New insights into the reactivity of nitrogen dioxide with substituted phenols: A solvent effect

Various alkyl-substituted phenols react readily with nitrogen dioxide (.NO2) in different solvents at room temperature. In all cases nitration is the major reaction and leads to the formation of mono- and dinitrophenols and 4-nitrocyclohexa-2,5-dienones from 2,4,6-tri-substituted phenols. Oxidation, dimerisation and, in one case, nitrosation are also observed. The reaction pathway followed changes according to the solvent and to the nature and the number of substituents on the phenolic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.

Derivatives of 2-aminopyridines, their use as medicaments and pharmaceutical compositions containing them

A compound of the formula wherein the substituents are defined as in the specification and their pharmaceutically acceptable salts having NOS and ROS activity.

New derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.