619-08-9

Usage

Uses

Used in Dye Industry:
2-Chloro-4-nitrophenol is used as a building block for the synthesis of various dyes. Its chemical structure allows for the creation of a diverse array of colored compounds, making it a valuable component in the development of new dyes.
Used in Plastics Industry:
In the plastics industry, 2-Chloro-4-nitrophenol serves as a building block for the production of certain types of plastics. Its incorporation into the polymer structure can enhance specific properties, such as color, stability, or durability.
Used in Explosives Industry:
2-Chloro-4-nitrophenol is utilized as a building block in the manufacturing of explosives. Its reactivity and the presence of the nitro group make it suitable for use in the formulation of various explosive compounds.
Used as a Catalytic Agent:
2-Chloro-4-nitrophenol acts as a catalytic agent in certain chemical reactions, facilitating the conversion of reactants to products and improving the efficiency of the process.
Used as a Petrochemical Additive:
In the petrochemical industry, 2-Chloro-4-nitrophenol is employed as an additive to enhance the performance of fuels and other petrochemical products. Its addition can lead to improved combustion, reduced emissions, or increased stability.
Used in Organic Synthesis:
2-Chloro-4-nitrophenol is a key intermediate in organic synthesis, where it can be used to produce a variety of other chemicals and compounds. Its versatility and reactivity make it a valuable starting material for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
For example, 2-Chloro-4-nitrophenol can react with sulfuric acid dimethyl ester to produce 2-chloro-4-nitro-anisole. This reaction requires the use of reagents such as K2CO3 and xylene, demonstrating its utility in the synthesis of complex organic molecules.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H4ClNO3/c7-5-3-4(8(10)11)1-2-6(5)9/h1-3,9H/p-1

Upstream product

• 100-02-7 4-nitro-phenol 
• 36942-09-3 N,N-dichlorourea 
• 102-71-6 triethanolamine 
• 99-54-7 3,4-dichloronitrobenzene 
• 109-95-5 ethyl nitrite 
• 6358-09-4 2-amino-6-chloro-4-nitrophenol 
• 95-57-8 2-monochlorophenol 
• 3964-56-5 4-bromo-2-chlorophenol 
• 111-42-2 2,2'-iminobis[ethanol] 
• 88-75-5 2-hydroxynitrobenzene 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 121-73-3 3-Nitrochlorobenzene 
• 73759-23-6 Phosphoric acid 2-chloro-4-nitro-phenyl ester 2-ethylamino-ethyl ester 
• 73759-20-3 Phosphoric acid 2-chloro-4-nitro-phenyl ester 2-(2,2,2-trifluoro-ethylamino)-ethyl ester; hydrochloride 

Downstream Products

• 100388-41-8 4-[2-(2-chloro-4-nitro-phenoxy)-ethyl]-morpholine 
• 99055-00-2 6,6'-dichloro-4,4'-dinitro-2,2'-methanediyl-di-phenol 
• 127679-80-5 4-Chloro-2,6-bis<(5-nitro-2-hydroxyphenyl)methyl>phenol 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 946-31-6 2-chloro-4,6-dinitro-phenol 
• 3964-54-3 3-chloro-4-hydroxyacetanilide 
• 3964-52-1 2-chloro 4-aminophenol 
• 41350-07-6 2-chloro p-benzoquinone⁽⁴⁾ chlorimide 
• 20294-55-7 2-bromo-6-chloro-4-nitrophenol 
• 2463-84-5 dicapthon 
• 108631-20-5 diethyl-[2-(2-chloro-4-nitro-phenoxy)-ethyl]-amine; hydrochloride 
• 64165-35-1 5-chloro-6-hydroxyquinoline 
• 4920-79-0 2-chloro-4-nitroanisole 
• 5226-63-1 1,4-Bis-(2-chlor-4-nitrophenoxy)-butan 

Relevant academic research and scientific papers

Superagonist, Full Agonist, Partial Agonist, and Antagonist Actions of Arylguanidines at 5-Hydroxytryptamine-3 (5-HT3) Subunit A Receptors

Introduction of minor variations to the substitution pattern of arylguanidine 5-hydroxytryptamine-3 (5-HT3) receptor ligands resulted in a broad spectrum of functionally-active ligands from antagonist to superagonist. For example, (i) introduction of an additional Cl-substituent(s) to our lead full agonist N-(3-chlorophenyl)guanidine (mCPG, 2; efficacy % = 106) yielded superagonists 7-9 (efficacy % = 186, 139, and 129, respectively), (ii) a positional isomer of 2, p-Cl analog 11, displayed partial agonist actions (efficacy % = 12), and (iii) replacing the halogen atom at the meta or para position with an electron donating OCH3 group or a stronger electron withdrawing (i.e., CF3) group resulted in antagonists 13-16. We posit based on combined mutagenesis, crystallographic, and computational analyses that for the 5-HT3 receptor, the arylguanidines that are better able to simultaneously engage the primary and complementary subunits, thus keeping them in close proximity, have greater agonist character while those that are deficient in this ability are antagonists.

Joint X-ray crystallographic and molecular dynamics study of cellobiohydrolase i from Trichoderma harzianum: Deciphering the structural features of cellobiohydrolase catalytic activity

Aiming to contribute toward the characterization of new, biotechnologically relevant cellulolytic enzymes, we report here the first crystal structure of the catalytic core domain of Cel7A (cellobiohydrolase I) from the filamentous fungus Trichoderma harzianum IOC 3844. Our structural studies and molecular dynamics simulations show that the flexibility of Tyr260, in comparison with Tyr247 from the homologous Trichoderma reesei Cel7A, is enhanced as a result of the short side-chains of adjacent Val216 and Ala384 residues and creates an additional gap at the side face of the catalytic tunnel. T. harzianum cellobiohydrolase I also has a shortened loop at the entrance of the cellulose-binding tunnel, which has been described to interact with the substrate in T. reesei Cel7A. These structural features might explain why T. harzianum Cel7A displays higher kcat and Km values, and lower product inhibition on both glucoside and lactoside substrates, compared with T. reesei Cel7A. 2012 The Authors Journal compilation

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Kinetics and mechanism of trichloroisocyanuric acid/NaNO2-triggered nitration of aromatic compounds under acid-free and Vilsmeier-Haack conditions

Kinetics and mechanism of nitration of aromatic compounds using trichloroisocyanuric acid (TCCA)/NaNO2, TCCA-N,N-dimethyl formamide (TCCA-DMF)/NaNO2, and TCCA-N,N-dimethyl acetamide (TCCA-DMA)/NaNO2 under acid-free and Vilsmeier-Haack conditions. Reactions followed second-order kinetics with a first-order dependence on [Phenol] and [Nitrating agent] ([TCCA], [(TCCA-DMF)], or [(TCCA-DMA)] >> [NaNO2]). Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups, but did not fit well into the Hammett's theory of linear free energy relationship or its modified forms like Brown-Okamoto or Yukawa-Tsuno equations. Rate data were analyzed by Charton's multiple linear regression analysis. Isokinetic temperature (β) values, obtained from Exner's theory for different protocols, are 403.7?K (TCCA-NaNO2), 365.8?K (TCCA-DMF)/NaNO2, and 358?K (TCCA-DMA)/NaNO2. These values are far above the experimental temperature range (303-323?K), indicating that the enthalpy factors are probably more important in controlling the reaction.

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

Method for hydrolyzing nitroaniline substances into phenol

The invention discloses a method for hydrolyzing nitroaniline substances into phenol. The method comprises the following steps: mixing the nitroaniline substances, a catalyst and inorganic base whichare used as raw materials with water used as a solvent, adding the mixture to a reactor, sealing the reactor, and heating the reactor to 100-190 DEG C for a reaction for 2-8 h; cooling an obtained reaction solution to room temperature, then, adjusting pH to 1-2, and washing and drying obtained precipitates to obtain the product, namely, nitrophenol substances. The nitrophenol substances are synthesized with the method, the utilization rate of the raw materials is high, expensive catalysts are not used, emission of three wastes is reduced, the production cost is reduced, and the product has high purity, high yield and good industrial application values.

Sodium perborate/NaNO2/KHSO4-triggered synthesis and kinetics of nitration of aromatic compounds

Sodium perborate (SPB) was used as efficient green catalyst for NaNO2/KHSO4-mediated nitration of aromatic compounds in aqueous acetonitrile medium. Synthesis of nitroaromatic compounds was achieved under both conventional and solvent-free microwave conditions. Reaction times were comparatively shorter in the microwave-assisted than conventional reaction. The reaction kinetics for nitration of phenols in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [Phenol], [NaNO2], and [SPB]. Reaction rates accelerated with introduction of electron-donating groups but retarded with electron-withdrawing groups. Kinetic results did not fit well quantitatively with Hammett’s equation. Observed deviations from linearity were addressed in terms of exalted Hammett’s constants (σˉ or σeff), para resonance interaction energy (ΔΔGp) parameter, and Yukawa–Tsuno parameter (r). This term provides a measure of the extent of resonance stabilization for a reactive structure that builds up charge (positive) in its transition state. The observed negative entropy of activation (?ΔS#) suggests greater solvation and/or cyclic transition state before yielding products.

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl

Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.

UGT74AN1, a Permissive Glycosyltransferase from Asclepias curassavica for the Regiospecific Steroid 3-O-Glycosylation

A permissive steroid glycosyltransferase (UGT74AN1) from Asclepias curassavica exhibited robust capabilities for the regiospecific C3 glycosylation of cardiotonic steroids and C21 steroid precursors, and unprecedented promiscuity toward 53 structurally diverse natural and unnatural compounds to form O-, N-, and S-glycosides, along with the catalytic reversibility for a one-pot transglycosylation reaction. These findings highlight UGT74AN1 as the first regiospecific catalyst for cardiotonic steroid C3 glycosylation and exhibit significant potential for glycosylation of diverse bioactive molecules in drug discovery.