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Usage

Uses

Used in Pesticide Industry:
4-Chloro-2,6-dinitrophenol is used as a pesticide for controlling pests in agricultural settings. Its high toxicity makes it effective in eliminating a wide range of pests, but also necessitates strict handling and application protocols to minimize exposure risks.
Used in Wood Preservation Industry:
In the wood preservation industry, 4-Chloro-2,6-dinitrophenol is used as a wood preservative to protect against decay, fungi, and insect infestation. Its effectiveness in preserving wood makes it a valuable component in the production of treated lumber and other wood products.
Used in Weight Loss Aids (Historically):
Although not approved for human consumption and banned by regulatory agencies, 4-Chloro-2,6-dinitrophenol has been historically used as a weight loss aid due to its ability to increase metabolism and burn fat. However, its extreme toxicity and potential for misuse make it a highly regulated and controlled substance, and it is no longer used for this purpose.

InChI:InChI=1/C6H3ClN2O5/c7-3-1-4(8(11)12)6(10)5(2-3)9(13)14/h1-2,10H

Upstream product

• 110-86-1 pyridine 
• 6302-58-5 2,6-dinitro-4-chloroanisole 
• 623-12-1 4-chloromethoxybenzene 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 89-64-5 p-chloro-o-nitrophenol 
• 609-89-2 2,4-dichloro-6-nitrophenol 
• 88-89-1 2,4,6-Trinitrophenol 
• 106-48-9 4-chloro-phenol 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 876-27-7 4-chlorophenyl acetate 
• 3229-70-7 phenolate 
• 46278-25-5 4-Chloro-2,6-dinitro-phenol anion 
• 18716-27-3 tribenzylamine; protonated form 
• 7697-37-2 nitric acid 

Downstream Products

• 2213-82-3 2,5-dichloro-1,3-dinitrobenzene 
• 14571-91-6 (4-Chloro-phenyl)-carbamic acid 4-chloro-2,6-dinitro-phenyl ester 
• 14571-84-7 Methyl-carbamic acid 4-chloro-2,6-dinitro-phenyl ester 
• 14571-86-9 Butyl-carbamic acid 4-chloro-2,6-dinitro-phenyl ester 
• 46278-25-5 4-Chloro-2,6-dinitro-phenol anion 
• 18716-27-3 tribenzylamine; protonated form 
• 123871-65-8 4-Chloro-2,4,6-trinitro-cyclohexa-2,5-dienone 
• 123871-64-7 4-Chloro-2,6,6-trinitro-cyclohexa-2,4-dienone 
• 15969-10-5 2-bromo-4-chloro-6-nitro-phenol 
• 10156-68-0 4-chloro-N,N-dimethyl-2,6-dinitroaniline 
• 39522-55-9 1-Nitro-3-chlorphenoxazin 
• 5388-62-5 4-chloro-2,6-dinitroaniline 
• 68151-95-1 Dimethyl-thiocarbamic acid S-[4-chloro-2-(5-chloro-2-dimethylcarbamoylsulfanyl-3-nitro-phenyldisulfanyl)-6-nitro-phenyl] ester 
• 16771-05-4 2'-Brom-,4-chlor-2,6-dinitro-diphenylsulfid 

Relevant academic research and scientific papers

Semiquinone-bridged bisdithiazolyl radicals as neutral radical conductors

Semiquinone-bridged bisdithiazolyls 3 represent a new class of resonance-stabilized neutral radical for use in the design of single-component conductive materials. As such, they display electrochemical cell potentials lower than those of related pyridine-bridged bisdithiazolyls, a finding which heralds a reduced on-site Coulomb repulsion U. Crystallographic characterization of the chloro-substituted derivative 3a and its acetonitrile solvate 3a·MeCN, both of which crystallize in the polar orthorhombic space group Pna21, revealed the importance of intermolecular oxygen-to-sulfur (CO...SN) interactions in generating rigid, tightly packed radical π-stacks, including the structural motif found for 3a·MeCN in which radicals in neighboring π-stacks are locked into slipped-ribbon-like arrays. This architecture gives rise to strong intra- and interstack overlap and hence a large electronic bandwidth W. Variable-temperature conductivity measurements on 3a and 3a·MeCN indicated high values of θ(300 K) (>10 -3 S cm-1) with correspondingly low thermal activation energies Eact, reaching 0.11 eV in the case of 3a·MeCN. Overall, the strong performance of these materials as f = 1/ 2 conductors is attributed to a combination of low U and large W. Variable-temperature magnetic susceptibility measurements were performed on both 3a and 3a·MeCN. The unsolvated material 3a orders as a spin-canted antiferromagnet at 8 K, with a canting angle φ = 0.14° and a coercive field Hc = 80 Oe at 2 K.

PKa values of chiral Bronsted acid catalysts: Phosphoric acids/amides, sulfonyl/sulfuryl imides, and perfluorinated TADDOLs (TEFDDOLs)

Measure what is measurable, and make measurable what is not so! This timeless quotation by Galileo forms the basis of all quantitative understanding, including asymmetric organocatalysis. We report pKa values for 15 chiral Bronsted acid catalysts in DMSO solutions (see scheme): the strongest acids were bis-sulfonyl/sulfuryl imides (pKa=1.7-1.9) followed by phosphoric acids/amides (pKa=2.4-4.2). A new class of chiral Bronsted acids, tetrakis-perfluoroalkyl analogues of TADDOLs (TEFDDOLs) have pKas from 2.4 to 5.7.

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.

Nitrogen Oxides and Nitric Acid Enable the Sustainable Hydroxylation and Nitrohydroxylation of Benzenes under Visible Light Irradiation

A new type of waste recycling strategy is described in which nitrogen oxides or nitric acid are directly employed in photocatalyzed hydroxylations and nitrohydroxylations of benzenes. Through these transformations, otherwise costly denitrification can be combined with the synthesis of valuable compounds for various applications.

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.

Synthesis of 6-aminobenzopentathiepines by reactions of 4-nitrobenzodithiol-2-ones with NaHS

The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6- aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 ? F, Cl > CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.

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.

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.

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.