609-89-2

Basic information

• Product Name: 2,4-Dichloro-6-nitrophenol
• Synonyms: 2,4-Dichlor-6-nitrofenol;2,4-dichloro-6-nitro-pheno;2-Nitro-4,6-dichlorophenol;2,4-DICHLORO-6-NITROPHENOL;Moistsolidcontaining20%water;2,4-Dichloro-6-nitrophenol, moist solid containing 20% water, 98%;4,6-Dichloro-2-nitrophenol;Phenol, 2,4-dichloro-6-nitro-
• CAS NO: 609-89-2
• Molecular Formula: C₆H₃Cl₂NO₃
• Molecular Weight: 208
• EINECS: 210-202-2
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 609-89-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 118-120 °C(lit.)
• Boiling Point: 242.8 °C at 760 mmHg
• Flash Point: 100.6 °C
• Appearance: Yellow/Powder
• Density: 1.5643 (rough estimate)
• Vapor Pressure: 0.0214mmHg at 25°C
• Refractive Index: 1.6390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4?+-.0.38(Predicted)
• BRN: 2050081
• CAS DataBase Reference: 2,4-Dichloro-6-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-6-nitrophenol(609-89-2)
• EPA Substance Registry System: 2,4-Dichloro-6-nitrophenol(609-89-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-41-20/21/22
• Safety Statements: 26-36/37/39-28
• RIDADR: UN 2811
• WGK Germany: 3
• RTECS: SL0350000
• F: 4.5
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 609-89-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow to orange powder

Uses

2,4-Dichloro-6-nitrophenol, a specific inhibitor of sulfotransferases, was used to reduce the neosynthesis of [3H] pregnenolone sulfate (Δ5PS) and [3H]dehydroepiandrosterone sulfate (DHEAS).

General Description

The FT-Raman and FTIR spectra of 2,4-dichloro-6-nitrophenol (2,4-DC6NP) was studied.

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 
• 320-72-9 3,5-dichlorosalicylic acid 
• 3229-70-7 phenolate 
• 7697-37-2 nitric acid 
• 120-83-2 2,4-dichlorophenol 
• 7782-50-5 chlorine 
• 88-75-5 2-hydroxynitrobenzene 
• 7647-01-0 hydrogenchloride 
• 540-80-7 tert.-butylnitrite 
• 28689-08-9 1,5-dichloro-2,3-dinitrobenzene 
• 83732-61-0 3-chloro-4-hydroxy-5-nitro-benzenesulfonic acid 
• 26281-43-6 3,5-dichloro-2-hydroxybenzenesulfonic acid 
• 4524-77-0 2-bromo-4,6-dichlorophenol 
• 64-19-7 acetic acid 

Downstream Products

• 32314-11-7 carbonic acid ethyl ester-(2,4-dichloro-6-nitro-phenyl ester) 
• 773-76-2 chloroxine 
• 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 
• 4769-91-9 Methoxymethyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 
• 46008-81-5 tribromo-chloro-[1,4]benzoquinone 
• 55202-45-4 2-acetamido-4,6-dichlorophenol 
• 88-87-9 4-chloro-2,6-dinitrophenol 
• 527-62-8 2,4-dichloro-6-aminophenol 
• 1313588-23-6 C₂₃H₁₉Cl₂F₃N₄O₂ 
• 1313588-17-8 C₂₀H₁₄Cl₃F₃N₄O₂ 
• 1313588-16-7 C₂₂H₁₉Cl₂F₃N₄O₃ 
• 1313588-15-6 C₂₁H₁₆Cl₃F₃N₄O₃ 

Relevant articles and documents

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 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.