609-89-2

Usage

Uses

Used in Pharmaceutical Research:
2,4-Dichloro-6-nitrophenol is used as a research chemical for studying the inhibition of sulfotransferases. Its application in this field is crucial for understanding the role of these enzymes in various biological processes and their potential as therapeutic targets.
Used in Steroid Synthesis Inhibition:
In the field of endocrinology and biochemistry, 2,4-Dichloro-6-nitrophenol is used as an inhibitor to reduce the neosynthesis of [3H] pregnenolone sulfate (Δ5PS) and [3H]dehydroepiandrosterone sulfate (DHEAS). This application aids in the study of steroid hormone synthesis and its regulation, which is essential for understanding various physiological and pathological conditions related to steroid metabolism.
Used in Spectroscopic Studies:
The chemical properties of 2,4-Dichloro-6-nitrophenol, including its FT-Raman and FTIR spectra, are of interest to researchers in the field of spectroscopy. These studies can provide valuable insights into the molecular structure and interactions of 2,4-DC6NP, which can be useful for its further development and application in various scientific and industrial contexts.

Purification Methods

Crystallise the chloronitrophenol from AcOH. [Beilstein 6 IV 1358.]

InChI:InChI=1/C6H3Cl2NO3/c7-3-1-4(8)6(10)5(2-3)9(11)12/h1-2,10H/p-1

Synthetic route

2,4-dichlorophenol (120-83-2) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With sulfuric acid; nitric acid at 40℃; for 0.0152778h; Temperature; Flow reactor;	95%
With NO+*18-crown-6*H(NO3)2- In acetone at 20℃; for 0.0833333h; Nitration;	94%
With poly(4-vinylpyridinium nitrate); silica supported sulfuric acid In dichloromethane at 20℃; for 3.33333h;	90%

tert.-butylnitrite (540-80-7) + 2,4-dichlorophenol (120-83-2) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With water In tetrahydrofuran at 25℃; for 2.5h; Schlenk technique;	75%

1,3-dichloro-4-methoxybenzene (553-82-2) → 2-methoxy-3,5-dichloronitrobenzene (37138-82-2) + 2,4-dichloro-6-nitrophenol (609-89-2) + 2,4-dicloro-5-nitroanisole (85829-14-7)

Conditions	Yield
With nitric acid In sulfuric acid at 25℃; Rate constant; Product distribution; various acid concentrations;	A 29.6% B 67.6% C 1.2%

2-hydroxynitrobenzene (88-75-5) → p-chloro-o-nitrophenol (89-64-5) + 2,4-dichloro-6-nitrophenol (609-89-2) + 2-chloro-6-nitrophenol (603-86-1)

Conditions	Yield
With oxone; potassium chloride In acetonitrile at 20℃; for 48h;	A 39% B 18% C 6%

2-Nitroanisole (91-23-6) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With aluminium trichloride; sulfuryl dichloride

p-hydoroxybenzenesulfonic acid (98-67-9) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With nitric acid nachfolgend Chlorieren;

2-methoxy-3,5-dichloronitrobenzene (37138-82-2) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With hydrogen bromide; acetic acid

2-bromo-4,6-dichlorophenol (4524-77-0) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With acetic acid; sodium nitrite

p-chloro-o-nitrophenol (89-64-5) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With chlorine

3,5-dichlorosalicylic acid (320-72-9) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With nitric acid; acetic acid

4-hydroxy-3-nitrobenzene sulfonic acid (616-85-3) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With water; chlorine

1,5-dichloro-2,3-dinitrobenzene (28689-08-9) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With potassium hydroxide

acetyl chloride (75-36-5) + phenol (108-95-2) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With cuprous nitrate

2-hydroxynitrobenzene (88-75-5) → 2,4-dichloro-6-nitrophenol (609-89-2)

Conditions	Yield
With potassium hydroxide; chlorine
With hydrogenchloride; sodium hypochlorite at 15 - 20℃;
(i) aq. KOH, (ii) Cl2, AlCl3, I2; Multistep reaction;
Multi-step reaction with 2 steps 1: beim Chlorieren 2: chlorine View Scheme

chloropicrin (76-06-2) + phenol (108-95-2) → 2,4-dichloro-6-nitrophenol (609-89-2)

Upstream product

• 91-23-6 2-Nitroanisole 
• 98-67-9 p-hydoroxybenzenesulfonic acid 
• 37138-82-2 2-methoxy-3,5-dichloronitrobenzene 
• 4524-77-0 2-bromo-4,6-dichlorophenol 
• 89-64-5 p-chloro-o-nitrophenol 
• 320-72-9 3,5-dichlorosalicylic acid 
• 616-85-3 4-hydroxy-3-nitrobenzene sulfonic acid 
• 28689-08-9 1,5-dichloro-2,3-dinitrobenzene 
• 75-36-5 acetyl chloride 
• 108-95-2 phenol 
• 120-83-2 2,4-dichlorophenol 
• 88-75-5 2-hydroxynitrobenzene 
• 76-06-2 chloropicrin 
• 553-82-2 1,3-dichloro-4-methoxybenzene 

Downstream Products

• 527-62-8 2,4-dichloro-6-aminophenol 
• 88-87-9 4-chloro-2,6-dinitrophenol 
• 46008-81-5 tribromo-chloro-[1,4]benzoquinone 
• 55202-45-4 2-acetamido-4,6-dichlorophenol 
• 32314-11-7 carbonic acid ethyl ester-(2,4-dichloro-6-nitro-phenyl ester) 
• 37169-10-1 acetic acid-(2,4-dichloro-6-nitro-phenyl ester) 
• 773-76-2 chloroxine 
• 14571-89-2 Propyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 14571-78-9 Octadecyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 14571-83-6 m-Tolyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 14571-81-4 (4-Chloro-phenyl)-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 14628-75-2 (2-Chloro-phenyl)-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 14571-87-0 Methyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 4769-91-9 Methoxymethyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 

Relevant academic research and scientific papers

Preparation method of pentachloride intermediate 2, 4 - dichloro -6 - nitrophenol (by machine translation)

To the preparation method, 2, 4 - dichlorophenol sulfuric acid solution and nitric acid solution are respectively added to a continuous flow micro-channel reactor, and subjected to preheating, mixing, nitration reaction to obtain -6 - 2 dichloro 4 -6 - 4 - 2 -nitrophenol. The method comprises the following steps of: preheating, mixing and nitration reaction, and carrying out nitrification reaction. The method has the advantages of being convenient, safe, efficient, small in process environment pollution and the like, and can effectively avoid the generation. (by machine translation)

Copper-mediated nitrosation: 2-nitrosophenolato complexes and their use in the synthesis of heterocycles

A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature.

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert -Butyl Nitrite

A radical-radical cross-coupling reaction of phenols with tert -butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C-N bonds under an air atmosphere at room temperature, providing the ortho -nitrated phenol derivative in moderate to good yields.

A practical approach for regioselective mono-nitration of phenols under mild conditions

Cu(NO3)2.3H2O was demonstrated to be an efficient, regioselective and inexpensive nitrating reagent for the synthesis of mono-nitro substituted phenolic compounds. 12 examples of different phenols were examined. Good yields (67-90%) have been achieved. ARKAT-USA, Inc.

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes

A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.

A new method for the mononitration of phenol derivatives by poly(4-vinylpyridinium nitrate) and silica sulfuric acid under mild conditions

This procedure works efficiently for high selective mono nitration of phenol and substituted phenol to corresponding nitro compounds in moderate to high yield using poly(4-vinylpyridinium nitrate) and silica sulfuric acid in dichloromethane at room temperature.

Melamine-(H2SO4)3 and PVP-(H 2SO4)n as solid acids: Synthesis and application in the first mono- and di-nitration of bisphenol A and other phenols

Melamine and poly vinylpyrrolidone (PVP) reacted with neat sulfuric acid readily to form two new organic solid acids namely melamine-(H 2SO4)3 and PVP-(H2SO 4)n. These solid acids were used for the first nitration of bisphenol A as well as other phenols in the presence of NH4NO 3. Mono- and di-nitro bisphenol A have been characterized with IR and 1H NMR techniques.

Mononitration of phenol derivatives by guanidinium nitrate and silica sulfuric acid under mild conditions

A mixture of guanidinium nitrate and silica sulfuric acid acts as mild and heterogeneous media for the efficient mono nitration of phenolic compounds in dichloromethane at room temperature.

A mild procedure for the preparation of o-nitrophenols by nitro urea or ammonium nitrate in the presence of silica sulfuric acid (SiO 2-OSO3H)

A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature. A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature.

Highly efficient, para-selective oxychlorination of aromatic compounds using potassium chloride and Oxone

A highly efficient, regioselective method for oxychlorination of aromatic compounds is possible through electrophilic substitution of chlorine generated in situ from KCl as a chlorine source and Oxone as an oxidant for the first time.