609-93-8

Usage

Uses

Used in Various Industries:
2,6-Dinitro-p-cresol is used as a chemical intermediate for the synthesis of various compounds and products. Its applications are similar to those of its isomer, 4,6-dinitro-o-cresol, which include its use in the production of dyes, pesticides, and other chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Dinitro-p-cresol is utilized as an antimicrobial agent, particularly for its antifungal and antibacterial properties. It can be found in the formulation of certain medications and topical ointments to combat infections.
Used in Dye Industry:
2,6-Dinitro-p-cresol is employed as a key component in the production of dyes, specifically for its ability to impart color to various materials. Its chemical properties make it suitable for use in the synthesis of a range of dyestuffs.
Used in Pesticide Industry:
In the pesticide industry, 2,6-Dinitro-p-cresol is used as an active ingredient in the development of certain pesticides. Its biocidal properties contribute to the control of pests and diseases in agriculture.
Used in Chemical Synthesis:
2,6-Dinitro-p-cresol serves as a valuable chemical intermediate in the synthesis of various organic compounds. Its unique structure allows for further modification and reaction with other chemicals, leading to the creation of new compounds with specific applications.

Safety Profile

Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other dinitrocresol entries.

Purification Methods

Recrystallise the cresol from EtOH. It is steam volatile. The piperidine salt has m 195o. [Beilstein 6 H 414, 6 II 391, 6 III 1390, 6 IV 2152.] TOXIC IRRITANT.

InChI:InChI=1/C7H6N2O5/c1-4-2-3-5(10)7(9(13)14)6(4)8(11)12/h2-3,10H,1H3

Upstream product

• 110-86-1 pyridine 
• 106-44-5 p-cresol 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 918-37-6 hexanitroethane 
• 509-14-8 tetranitromethane 
• 67-56-1 methanol 
• 104-93-8 p-methylanizole 
• 352-32-9 p-fluorotoluene 
• 563-41-7 semicarbazide hydrochloride 
• 127-09-3 sodium acetate 
• 622-60-6 1-ethoxy-4-methylbenzene 
• 618-85-9 3,5-dinitrotoluene 
• 2236-38-6 4-Methyl-1-(4-methylphenoxy)-2-nitrobenzene 

Downstream Products

• 29455-11-6 2,6-dinitro-4-methylanisole 
• 5264-65-3 3,5-Dinitro-4-chlorotoluene 
• 45742-37-8 2,6-diamino-p-cresol 
• 6265-07-2 2-nitro-4-methyl-6-amino-phenol 
• 83757-40-8 4-(4-methyl-2,6-dinitro-anilino)-phenol 
• 6393-42-6 4-methyl-2,6-dinitroaniline 
• 5465-75-8 toluene-4-sulfonic acid-(4-methyl-2,6-dinitro-phenyl ester) 
• 408337-60-0 (2,4-dinitro-phenyl)-(4-methyl-2,6-dinitro-phenyl)-ether 
• 78805-60-4 2-isopropyl-4-(2,6-dinitro-4-methylphenoxy)anisole 
• 78805-66-0 2-isopropyl-4-(2,6-diiodo-4-methylphenoxy)anisole 
• 854053-68-2 [1,4]benzoquinone-mono-(4-methyl-2,6-dinitro-phenylimine) 
• 855403-96-2 2-chloro-4-(4-methyl-2,6-dinitro-anilino)-phenol 

Relevant academic research and scientific papers

Nitration method for aryl phenol or aryl ether derivative

The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri-nitydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Nitration of phenolic compounds by antimony nitrate

Antimony nitrate is new compound to be an efficient nitration reagent in the nitration of phenolic compounds with high yields. This producerworks efficiently onmost of the examples, as a grinding nitration reaction, proceed very fast (～1 min) and thermogenic. Copyright Taylor & Francis Group, LLC.

PEG-N2O4: An efficient nitrating agent for the selective mono- and dinitration of phenols under mild conditions

N2O4 was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N2O4 (PEG-N2O4) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N2O4 at room temperature in moderate to high yields. Copyright Taylor & Francis Group, LLC.

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.

Nitration of phenolic compounds by metal-modified montmorillonite KSF

The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.

Highly efficient catalytic nitration of phenolic compounds by nitric acid with a recoverable and reusable Zr or Hf oxychloride complex and KSF

Phenolic compounds can be nitrated with 60% nitric acid (1.2 equiv.) in the presence of catalytic amounts of a Zr or Hf oxychloride complex and montmorillonite KSF to give the corresponding nitrated products in good yields in a heterogeneous catalytic system. The co-catalyst and montmorillon ite can be easily recovered and reused in the next batch of nitration. This is a practical process for the nitration of phenolic compounds in a clean way. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

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.