553-82-2

Basic information

• Product Name: 2,4-DICHLOROANISOLE
• Synonyms: 2,4-dichloro-1-methoxy-benzen;2,4-Dichloro-1-methoxybenzene;2,4-Dichloro-1-methoxy-benzene;Anisole, 2,4-dichloro-;Benzene, 1,3-dichloro-4-methoxy;2,4-DICHLOROANISOLE;2,4-DICHLOROMETHOXYBENZENE;1,3-DICHLORO-4-METHOXYBENZENE
• CAS NO: 553-82-2
• Molecular Formula: C₇H₆Cl₂O
• Molecular Weight: 177.03
• EINECS: 209-051-5
• Product Categories: Aromatic Ethers;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 553-82-2.mol

Chemical Properties

• Melting Point: 24-27 °C(lit.)
• Boiling Point: 110 °C (12 mmHg)
• Flash Point: >230 °F
• Appearance: clear, colorless liquid
• Density: 1.288 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: n20/D 1.561(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1940358
• CAS DataBase Reference: 2,4-DICHLOROANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLOROANISOLE(553-82-2)
• EPA Substance Registry System: 2,4-DICHLOROANISOLE(553-82-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/22
• Safety Statements: 37/39-26-23
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 553-82-2(Hazardous Substances Data)

Usage

Uses

Used in Consumer Products Industry:
2,4-Dichloroanisole is used as a contaminant in the production of various consumer products, most notably in the wine industry. Its presence, although unintended, can significantly impact the sensory characteristics of these products, leading to off-flavors and odors that can be detrimental to the overall quality and consumer experience.
As a contaminant, 2,4-dichloroanisole poses a challenge to the wine industry, as it can lead to the development of musty, moldy, or chemical-like aromas in the final product. This can result in a negative perception of the wine and may even lead to economic losses for producers. Efforts are being made to identify and mitigate the sources of this contaminant to ensure the production of high-quality wines.

InChI:InChI=1/C7H6Cl2O/c1-10-7-3-2-5(8)4-6(7)9/h2-4H,1H3

Upstream product

• 6505-37-9 2,6-dichloro-3-methoxybenzaldehyde 
• 623-12-1 4-chloromethoxybenzene 
• 766-51-8 2-Chloroanisole 
• 36309-68-9 p-methoxyphenyltellurium trichloride 
• 100-66-3 methoxybenzene 
• 7782-50-5 chlorine 
• 7553-56-2 iodine 
• 35113-90-7 2,4-dichloro-N,N-dimethylaniline 
• 865-33-8 potassium methanolate 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 67-56-1 methanol 
• 1435-48-9 1,3-dichloro-4-fluorobenzene 
• 541-73-1 1,3-Dichlorobenzene 
• 124-41-4 sodium methylate 

Downstream Products

• 99357-09-2 5,6′-methylenebis(2,4-dichlorophenol) 
• 107922-32-7 bis-(2,4-dichloro-5-methoxy-phenyl)-methane 
• 37138-82-2 2-methoxy-3,5-dichloronitrobenzene 
• 13543-09-4 2,4-dichlorophenoxymethyl chloride 
• 104392-33-8 dichloromethyl-(2,4-dichloro-phenyl)-ether 
• 50353-36-1 2,4-dichloro-1-trichloromethoxy-benzene 
• 126644-80-2 1,3-dichloro-4-methoxy-2-<2-(phenylsulfonyl)ethyl>benzene 
• 609-89-2 2,4-dichloro-6-nitrophenol 
• 85829-14-7 2,4-dicloro-5-nitroanisole 
• 26281-43-6 3,5-dichloro-2-hydroxybenzenesulfonic acid 
• 1219804-86-0 C₇H₃⁽²⁾H₄ClO 
• 623-12-1 4-chloromethoxybenzene 
• 100-66-3 methoxybenzene 
• 2401-24-3 2-chloro-5-methoxyaniline 

Relevant articles and documents

Fabrication of La2O3/Bi2O3/silver orthophosphate Heterojunction Catalyst for the Visible Light Mediated Remediation of Refractory Pollutants

The development of silver orthophosphate based ternary composite catalyst for the augmented visible light assisted photocatalytic abatement of toxic refractory pollutants was accepted. It was confounded that the synthesized catalyst effectively degrade toxic organic dyes including methylene blue (MB), methyl orange (MO), rhodamine B (RhB) and acid red 18 (AR 18) with complete decolourisation and above 90 % mineralization. The hazardous pesticides such as 2, 4-dichlorophenoxyacetic acid (2,4-D), highly toxic insecticide acephate and the pharmaceutical antibiotic tetracycline were succesfully degraded. Here, it is the first time reporting La2O3/Bi2O3 doped silver orthophosphate ternary catalyst for the removal of toxic organic pollutants in a short time with excellent mineralization. The better reproducibility and accountable stability of the composite catalyst paved the way for making it a promising catalyst for future applications.

Organophotochemical SNAr Reactions of Mildly Electron-Poor Fluoroarenes

C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron-poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary to classical SNAr chemistry which generally requires basic reaction conditions and high temperatures, and provides products under non-basic conditions at ≈ 40 °C.

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.

Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis

Nucleophilic aromatic substitution (SNAr) is a direct method for arene functionalization; however, it can be hampered by low reactivity of arene substrates and their availability. Herein we describe a cation radical-accelerated nucleophilic aromatic substitution using methoxy- and benzyloxy-groups as nucleofuges. In particular, lignin-derived aromatics containing guaiacol and veratrole motifs were competent substrates for functionalization. We also demonstrate an example of site-selective substitutive oxygenation with trifluoroethanol to afford the desired trifluoromethylaryl ether.

Selective water-based oxychlorination of phenol with hydrogen peroxide catalyzed by manganous sulfate

An efficient method for the selective oxychlorination of phenol to 2,4-dichlorophenol catalyzed by manganous(ii) sulfate is developed using hydrogen chloride as a chlorinating source, hydrogen peroxide as an oxidant and water as a solvent. The catalyst has high activity and selectivity under mild conditions. The products are automatically isolated from aqueous solution, which also contains the catalyst at the end of the reaction, and hence product separation and catalyst recycling are both simple in this system. The performance of manganous(ii) sulfate with the oxidative chlorinating system HCl/H2O2 indicates that this is a promising synthetic method for the manufacture of various 2,4-dichlorophenol derivatives.

Benzene C-H Etherification via Photocatalytic Hydrogen-Evolution Cross-Coupling Reaction

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SELECTIVE HYDROLYSIS AND ALCOHOLYSIS OF CHLORINATED BENZENES

The present invention relates to a process for providing a compound of formula (I):, wherein R is hydrogen or R', wherein R' is –(C1-C4)alkyl, and Hal is a halogen, the process comprising the step of: reacting a compound of formula (II) wherein Hal is defined as above, with an alkali metal alkoxide of the formula XOR', wherein X is an alkali metal, and R' is defined as above.

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The present invention relates to a process for providing a compound of formula (I): wherein Hal is a halogen, the process comprising the step of: reacting a compound of formula (II) wherein Hal is defined as above, with an alkali metal sulfite of the formula X2SO3 and an alkali metal hydroxide of the formula YOH, wherein X and Y are independently selected from an alkali metal.