2423-71-4

Basic information

• Product Name: 2,6-DIMETHYL-4-NITROPHENOL
• Synonyms: 2,6-DIMETHYL-4-NITROPHENOL 98+%;2,6-Dimethyl-4-nitrophenol,4-Nitro-2,6-xylenol;2,6-DIMETHYL-4-NITROPHENOL FOR SYNTHESIS;4-Nitro-2,6-xylenol, 3,5-Dimethyl-4-hydroxynitrobenzene;2,6-Dimethyl-4-nitrophenol 98%;NSC 2990;2,6-Xylenol, 4-nitro-;4-Nitro-2,6-dimethylphenol
• CAS NO: 2423-71-4
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 219-353-9
• Mol File: 2423-71-4.mol

Chemical Properties

• Melting Point: 168 °C (dec.)(lit.)
• Boiling Point: 285.73°C (rough estimate)
• Flash Point: 145.3°C
• Appearance: /
• Density: 1.1820 (estimate)
• Vapor Pressure: 0.000145mmHg at 25°C
• Refractive Index: 1.5774 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: pK1:7.190 (25°C)
• Water Solubility: Insoluble in water.
• BRN: 1873275
• CAS DataBase Reference: 2,6-DIMETHYL-4-NITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYL-4-NITROPHENOL(2423-71-4)
• EPA Substance Registry System: 2,6-DIMETHYL-4-NITROPHENOL(2423-71-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: ZE8225000
• Hazardous Substances Data: 2423-71-4(Hazardous Substances Data)

Usage

Uses

Used in Bio-oil Production:
2,6-DIMETHYL-4-NITROPHENOL is used as a production compound for the creation of bio-oil from hardwood and softwood lignin. Its role in this process aids in the efficient conversion of lignin into a valuable energy source.
Used in Binding Studies:
2,6-DIMETHYL-4-NITROPHENOL is used as a study compound to investigate the disposition requirement for binding of p-nitrophenol and sodium p-nitrophenolate-like substrates with cyclohexaamylaose. This application helps in understanding the interaction between these substrates and the cyclohexaamylaose, which can be crucial for various chemical and biological processes.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2,6-DIMETHYL-4-NITROPHENOL is used as an internal standard in the determination of 4-nitrophenol and 3-methyl-4-nitrophenol in human urine by liquid chromatography combined with tandem mass spectrometry. Its use as an internal standard ensures accurate and reliable measurements of these compounds in urine samples, which can be significant for medical and toxicological assessments.

InChI:InChI=1/C8H9NO3/c1-5-3-7(9(11)12)4-6(2)8(5)10/h3-4,10H,1-2H3/p-1

Upstream product

• 123-75-1 pyrrolidine 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 96-22-0 pentan-3-one 
• 576-26-1 2.6-dimethylphenol 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 329770-09-4 (2,6-dimethyl-4-nitro-phenoxy)-acetone 
• 71-43-2 benzene 
• 181294-58-6 N-tert-butyl-β-formyl-β-nitroenamine 
• 1736-85-2 2-fluoro-1,3-dimethyl-5-nitrobenzene 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 1004-66-6 2-methoxy-1,3-dimethylbenzene 
• 60-29-7 diethyl ether 
• 4919-37-3 3,5-dimethyl-4-hydroxybenzoic acid 

Downstream Products

• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 156740-97-5 4-(4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene 
• 156740-77-1 3,5-dimethyl-4-(3'-isopropyl-4'-methoxyphenoxy)-nitrobenzene 
• 928790-01-6 1,3-dimethyl-5-nitro-2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxy)-benzene 
• 927267-41-2 1-(2,6-dimethyl-4-nitro-phenoxymethyl)-octahydro-quinolizine 
• 1231749-64-6 4-(6-chloro-pyrimidin-4-ylamino)-2,6-dimethyl-phenol 
• 1231748-53-0 3-{1-[6-(4-hydroxy-3,5-dimethyl-phenylamino)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one 
• 53906-84-6 2-bromo-1,3-dimethyl-5-nitrobenzene 
• 59557-90-3 4-bromo-3,5-dimethylaniline 
• 78668-13-0 dibromo-3,4 dimethyl-2,6 anisole 
• 25528-30-7 6-(2,6-dimethyl-phenoxy)-3-methoxy-2,4-dimethyl-aniline 
• 39785-37-0 4-amino-2,6-dimethylanisole 
• 25528-27-2 1-(2,6-dimethyl-phenoxy)-4-methoxy-3,5-dimethyl-2-nitro-benzene 
• 25528-31-8 3-Amino-4-(2,6-dimethyl-phenoxy)-2,6-dimethyl-phenol 

Relevant articles and documents

One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry

Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

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.

Improved Protocol for Mononitration of Phenols with Bismuth(III) and Iron(III) Nitrates

A simple and efficient multigram procedure was developed for the selective mononitration of various activated phenols. The reaction proceeded smoothly with 0.5 equivalents of Bi(NO3)3 · 5H2O or Fe(NO3)3 · 9H2O in acetone at ambient temperature or at reflux. The desired products were isolated in 62-93% total yield and essentially no overnitrated compounds were detected.

Nitration of phenolic compounds and oxidation of hydroquinones using tetrabutylammonium chromate and dichromate under aprotic conditions

In this work, we have reported a mild, efficient and selective method for the mononitration of phenolic compounds using sodium nitrite in the presence of tetrabutylammonium dichromate (TBAD) and oxidation of hydroquinones to quinones with TBAD in CH2Cl2. Using this method, high yields of nitrophenols and quinones were obtained under neutral aprotic conditions. Tetrabutylammonium chromate (TBAC) can also be used as oxidant at same conditions. Indian Academy of Sciences.

Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions

A mild, efficient and regioselective method for the mononitration of phenolic compounds is described using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid in CH2Cl2 at room temperature.

A convenient method for synthesizing modified 4-nitrophenols

β-Nitroenamine having a formyl group behaves as the synthetic equivalent of unstable nitromalonaldehyde upon treatment with ketones under basic conditions and leads to 2,6-disubstituted 4-nitrophenols. The present method is safer than the conventional one using sodium nitromalonaldehyde and enables the preparation of hitherto unknown nitrophenols.

Nitration of aromatic compounds by Zn(NO3)2· 2N2O4 and its charcoal-supported system

Zn(NO3)2·N2O4 and its charcoal supported system were found to be efficient nitrating agents. Mononitration of aromatic compounds such as benzene, alkyl benzenes, halobenzenes, nitrobenzene, anisol, and the highly selective mono-, di-, and trinitration of phenol, and dinitraion of substituted phenols were also performed in the presence of these reagents.

Silica-acetate complex of N2O4: A heterogeneous reagent for the selective nitration of phenols and nitrosation of thiols

Complexation of gaseous N2O4 with acylated silica gel affords an addition compound, which is an efficient heterogeneous reagent for the selective mono- and dinitration of phenol, substituted phenols and nitrosation of thiols.

Silica-polyethyleneglycols/N2O4 complexes as heterogeneous nitrating and nitrosating agents

Silica-chloride was reacted with different quantities of H(OCH2CH2)nOH (n = 2-4) to furnish silica-based linear polyethylene glycols and cyclic polyethylene glycolic ethers. The N2O4 complex of silica-tetraethylene glycolic ether (III) was selected and used as a stable, cheap, and heterogeneous silica-based reagent for the selective mono- and dinitration of phenols and nitrosation of thiols.

A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite

The reactivity of different phenol substrates with nitric oxide and peroxynitrite was investigated. In general, nitration is the major reaction with peroxynitrite, while reactions with aqueous solutions of nitric oxide led to mixtures of nitro and nitroso derivatives depending upon the phenol. Nitrosation occurs on phenol substrates bearing a free para- position with respect to the OH group with the exception of 1-naphthol, which afforded a 1:1 mixture of the 2- and the 4-nitroso derivatives. Chromans 7 and 8 showed the highest reactivity with peroxynitrite, which suggests that they can act as efficient scavengers of this toxic intermediate. In both cases the corresponding 5-nitro derivative was the only reaction product detected. Finally, the fact that chroman 8 reacts with nitric oxide to afford the p- quinone derivative 22a in 90% yield suggests that this antioxidant could also be of potential use as specific nitric oxide tracer in biological tissues.