619-08-9

Basic information

• Product Name: 2-Chloro-4-nitrophenol
• Synonyms: o-Chloro-p-nitrophenol;P-NITRO-O-CHLOROPHENOL;2-chloro-4-nitro-pheno;Nitrofungin;Nitrofurgin;Phenol, 2-chloro-4-nitro-;4-NITRO-2-CHLOROPHENOL;2-CHLORO-4-NITROPHENOL
• CAS NO: 619-08-9
• Molecular Formula: C₆H₄ClNO₃
• Molecular Weight: 173.55
• EINECS: 210-578-8
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenoles and thiophenoles;Alpha sort;C;CAlphabetic;CHEnvironmental Standards;Metabolites;Pesticides&Metabolites;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 619-08-9.mol
• Article Data: 82

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 290.6 °C at 760 mmHg
• Flash Point: 129.6 °C
• Appearance: White to beige/Crystalline Powder or Crystals
• Density: 1.4914 (rough estimate)
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.43±0.22(Predicted)
• Water Solubility: slightly soluble
• BRN: 2046372
• CAS DataBase Reference: 2-Chloro-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitrophenol(619-08-9)
• EPA Substance Registry System: 2-Chloro-4-nitrophenol(619-08-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-37/39
• RIDADR: 2811
• WGK Germany: 3
• RTECS: SK5075000
• TSCA: Yes
• Hazardous Substances Data: 619-08-9(Hazardous Substances Data)

Usage

Description

2-Chloro-4-nitrophenol is an organic compound characterized by its chlorine and nitro functional groups. It is a versatile chemical intermediate with a wide range of applications across different industries due to its reactivity and functional group properties.

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

• 99-54-7 3,4-dichloronitrobenzene 
• 95-57-8 2-monochlorophenol 
• 3964-56-5 4-bromo-2-chlorophenol 
• 553-79-7 2-amino-4-nitro-1-propoxybenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 93749-97-4 2-chloro-4-nitrophenyl 4-hydroxybenzoate 
• 100-02-7 4-nitro-phenol 
• 14070-51-0 N-chlorosaccharin 
• 18855-84-0 2-chloro-4-nitrophenyl acetate 
• 109-73-9 N-butylamine 
• 163685-03-8 2-(2-Chloro-4-nitro-phenoxy)-4,6-dimethoxy-[1,3,5]triazine 
• 108-95-2 phenol 
• 110-91-8 morpholine 
• 28177-48-2 2,6-difluorophenol 

Downstream Products

• 2463-84-5 dicapthon 
• 31191-40-9 1-[2-(2-Bromo-ethoxy)-ethoxy]-2-chloro-4-nitro-benzene 
• 14571-93-8 Propyl-carbamic acid 2-chloro-4-nitro-phenyl ester 
• 31191-51-2 4-[6-(2-Chloro-4-nitro-phenoxy)-hexyloxy]-benzenesulfonyl fluoride 
• 5226-65-3 1,6-Bis-(2-chlor-4-nitrophenoxy)-hexan 
• 31191-39-6 1-(6-Bromo-hexyloxy)-2-chloro-4-nitro-benzene 
• 55560-32-2 C₁₁H₁₅Cl₂N₂O₃PS 
• 5226-66-4 1,8-Bis-(2-chlor-4-nitrophenoxy)-octan 
• 40888-27-5 2-Chloro-1-(2-chloro-1,1,2-trifluoro-ethoxy)-4-nitro-benzene 
• 28253-77-2 Thiophosphoric acid O-(2-chloro-4-nitro-phenyl) ester O'-(2-ethoxy-ethyl) ester O''-methyl ester 
• 5226-68-6 1,10-Bis-(2-chlor-4-nitrophenoxy)-decan 
• 38524-61-7 Thiophosphoric acid O-(2-chloro-4-nitro-phenyl) ester O'-ethyl ester S-propyl ester 
• 71457-70-0 2-Chlor-4-nitrophenyl-phenyl-phosphorchloridat 
• 42585-05-7 C₁₀H₁₃Cl₂N₂O₃PS 

Relevant articles and documents

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.

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.

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.

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.