13673-92-2

Usage

Uses

Used in Chemical Synthesis:
3,5-Dichlorocatechol 97 is used as an intermediate in the synthesis of various organic compounds, particularly those involving the catechol structure. Its unique chloro substitution at the 3rd and 5th positions allows for specific reactivity and functional group manipulation in chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-dichlorocatechol 97 is utilized as a building block for the development of novel drugs with potential therapeutic applications. Its unique chemical structure can be exploited to design and synthesize new molecules with desired pharmacological properties.
Used in Environmental Applications:
3,5-Dichlorocatechol 97 can be employed in environmental applications, such as the degradation of pollutants or the removal of toxic substances from the environment. Its chemical properties may allow it to interact with and neutralize harmful compounds, contributing to environmental remediation efforts.
Used in Material Science:
In the field of material science, 3,5-dichlorocatechol 97 can be used to develop new materials with specific properties. Its unique structure and reactivity can be leveraged to create materials with enhanced performance characteristics, such as improved stability, strength, or conductivity.
Used in Analytical Chemistry:
3,5-Dichlorocatechol 97 can be utilized as a reference compound or a standard in analytical chemistry for the calibration of instruments and the development of new analytical methods. Its distinct chemical properties make it a valuable tool for researchers in this field.

InChI:InChI=1/C6H4Cl2O2/c7-3-1-4(8)6(10)5(9)2-3/h1-2,9-10H

Upstream product

• 90-60-8 3,5-dichlorosalicyclaldehyde 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 56-23-5 tetrachloromethane 
• 7722-84-1 dihydrogen peroxide 
• 120-83-2 2,4-dichlorophenol 
• 21405-51-6 3,5-dichlorocyclohexa-3,5-diene-1,2-dione 
• 591-35-5 3,5-dichlorophenol 
• 3380-34-5 triclosan 
• 88-06-2 2,4,6-Trichlorophenol 

Downstream Products

• 17180-85-7 2,4-Dichloro-6-hydroxyphenoxyacetic acid 
• 21405-51-6 3,5-dichlorocyclohexa-3,5-diene-1,2-dione 
• 90283-01-5 3,5-dichloro-1,2-dimethoxybenzene 
• 32558-07-9 3,5-Dichloro-2-(2-diethylamino-ethoxy)-phenol 
• 32520-85-7 2-(2-Amino-ethoxy)-4,6-dichloro-phenol 
• 32520-78-8 2-(2-Amino-ethoxy)-3,5-dichloro-phenol 
• 99847-06-0 (2,4-dichloro-6-methoxy-phenoxy)-acetic acid 
• 706808-92-6 Fe(4,7-dimethyl-1,10-phenanthroline)3⁽²⁺⁾ 
• 931-17-9 1,2-Cyclohexanediol 
• 108-94-1 cyclohexanone 
• 108-93-0 cyclohexanol 
• 108-95-2 phenol 
• 32520-80-2 3,5-Dichloro-2-(2-dimethylamino-ethoxy)-phenol 
• 151143-60-1 2,6-dichloro-3,4-dimethoxynitrobenzene 

Relevant academic research and scientific papers

A detailed kinetic study of the direct photooxidation of 2,4,6-trichlorophenol

The direct photodegradation of 2,4,6-trichlorophenol (TCP) by UV–vis light was studied in aqueous solution in order to analyze the mechanism of the photochemical process and to determine the kinetic parameters including the quantum yield. Based on initial rate studies at different overall volumes and illumination patterns, it was proved that the rate of the process is directly proportional to the intensity of irradiating light. A significant, but moderate acceleration of the reaction rate with increasing temperature was revealed between 5.0 and 35.0?°C, which could be interpreted readily by assuming that the excited state of TCP is involved in two competing processes. High pressure liquid chromatography and mass spectrometry provided us information on the nature of the intermediates and the products formed. 2,6-Dichloro-1,4-benzoquinone, 3,5-dichloro-2-hydroxy-1,4-benzoquinone and 2,6-dihclorohydroxyquinone were detected as products and/or intermediates, and there were also hints of the formation of 3,5-dichlorobenzene-1,2-diol and 3,5-dichloro-1,2-benzoquinone. A possible degradation mechanism is proposed to interpret the kinetic findings.

Enhanced catalytic activity and thermal stability of 2,4-dichlorophenol hydroxylase by using microwave irradiation and imidazolium ionic liquid for 2,4-dichlorophenol removal

Enzymatic removal of 2,4-dichlorophenol (2,4-DCP) has become more attractive recently due to its high efficiency, low cost and environmental benefits. A highly active 2,4-DCP hydroxylase for 2,4-DCP removal was obtained and used in 2,4-DCP removal by employing microwave irradiation as a heating mode and ionic liquid (IL) as an additive. Both [EMIM][PF6] (1-ethyl-3-methylimidazolium hexafluorophosphate) and microwave irradiation were found to increase the 2,4-DCP removal efficiency and the thermal stability of 2,4-DCP hydroxylase, and a further incremental effect of microwave irradiation and [EMIM][PF6] on improving the 2,4-DCP removal efficiency and enzymatic thermal stability was observed. Conditions for 2,4-DCP removal were optimized and the removal of 2,4-DCP was completed in 15 min at 25°C with 0.66 ± 0.015 U mg-1 enzyme activity under the optimum conditions, much faster than the present enzymatic removal route, which took several hours for complete 2,4-DCP removal. Only 30 min were required for complete 2,4-DCP removal by using the 2,4-DCP hydroxylase at 4°C, indicating its psychrotrophic adaptability. These results showed that the use of 2,4-DCP hydroxylase under microwave in [EMIM][PF6] is a fast, efficient and environmentally benign method for the removal of 2,4-DCP, and this method can be used over a wide temperature range.

A Simple Method for the Preparation of Dichlorocatechols.

Dichlorocatechols (DCC) are common metabolites in the aerobic degradation of dichlorobenzenes. Their synthesis is therefore possible either enzymatically, or chemically by several two-step-synthesis starting from cycloalkanones or suitable dichlorophenols. A modified ultrasonic Reimer/Tiemann reaction and subsequent Dakin oxidation was used to prepare 3,5-DCC and 4,5-DCC. A new UV-photoradical single step synthesis of 3,4-dichlorocatechol as well as 3,6-dichlorocatechol is described in detail. Mass spectral and 13C-NMR spectral data of all four dichlorocatechol isomers are presented.

Sensitized photooxidation of triclosan pesticide. A kinetic study in presence of vitamin B2

Kinetic and mechanistic aspects of Riboflavin (Rf, vitamin B2)-sensitized photochemical degradation of Triclosan (TCS) have been studied by time-resolved and stationary techniques. TCS is a broadly-used biocide, also employed in a series of industrial products as a multifunctional additive. Rf, in the presence of light and oxygen, generates singlet molecular oxygen (O2(1Δg)) and superoxide radical anion (O2[rad]–). Results indicate that TCS quenches the triplet excited state of Rf (3Rf*), O2(1Δg), and O2[rad]–. The reactive rate constant for the interaction TCS-O2(1Δg) is 62-faster in alkaline medium with respect to pH 7. Photosensitized degradation of TCS by Rf was much faster than for phenol, a model pollutant, in similar conditions of pH. Kinetic analysis indicated that the reaction of TCS with 3Rf* and/or O2[rad]– is the prevailing oxidative route. Based on the environmental importance of the TCS, the products were determined by UHPLC-MS / MS analysis.

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.

Aerobic organocatalytic oxidation of aryl aldehydes: Flavin catalyst turnover by Hantzsch's ester

The first Dakin oxidation fueled by molecular oxygen as the terminal oxidant is reported. Flavin and NAD(P)H coenzymes, from natural enzymatic redox systems, inspired the use of flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol % catalyst loading, 1 equiv of Hantzsch ester, and O2 or air as the stoichiometric oxidant source.

Influence of activated carbons on the kinetics and mechanisms of aromatic molecules ozonation

Companies have been looking for new methods for treating toxic or refractory wastewaters; which can mainly be used prior to or after or in connexion with biological treatment processes. This paper compares conventional ozone oxidation with activated carbon (AC) promoted ozone oxidation, which helps developing a mechanism involving HO{radical dot} radical. For a compound which is quite easy to oxidise, like 2,4-dichlorophenol (2,4-DCP) conventional ozonation is efficient enough to remove the initial molecule. The mechanism involved mainly consists of an electrophilic attack on the aromatic ring, which is activated by the donor effect of the -OH group, then followed by a 1,3 dipolar cycloaddition (Criegee mechanism) that leads to aliphatic species, mainly carboxylic acids. Yet, the addition of AC, through the presence of HO{radical dot} radical, enhances the removal of these species which are more refractory. For a refractory compound like nitrobenzene (NB), with a de-activated aromatic ring because of the attractive effect of -NO2, conventional ozonation is inefficient. On the contrary, this molecule can be quite easily removed with AC promoted oxidation and it is found that the mechanism (electrophilic attack followed by a 1,3 dipolar cycloaddition) is quite similar to the one corresponding to conventional ozonation, but with less selectivity. For both molecules, a mass balance has established that the by-products accounting for more than 75% of the remaining COD can be quantified. A significant part is composed of carboxylic acids (acetic, oxalic, etc.), which could afterwards be easily removed in an industrial wastewater treatment process followed by a final biological treatment step.

Kinetics of heterogeneous photocatalytic decomposition of 2,4-dichlorophenoxyacetic acid over titanium dioxide and zinc oxide in aqueous solution

The photocatalytic transformation of 2,4-D in aqueous solution containing a suspension of titanium dioxide or zinc oxide leads to the formation of intermediates which are totally mineralised to carbon dioxide and hydrogen chloride (2,4-dichlorophenol and chlorohydroquinone are the major intermediates). The products at the initial stage of the reaction were 2,4-dichlorophenol (2,4-DCP), chlorohydroquinone, 4-chloropyrocatechol, 2,4-dichloro-pyrocatechol and 1.4-chlorobenzoquinone. The initial rate of photodegradation was studied as a function of the initial concentration of reactants by the linearised form of the Langmuir-Hinshelwood equation, by which rate constants κ and equilibrium adsorption constants K were evaluated. These constants were calculated at different temperatures between 25 and 60°C. The photodegradation rate increased with increase of pH. The photocatalytic transformation of 2,4-D over titanium dioxide or zinc oxide in solution containing hydrogen peroxide was studied. The latter accelerated the reaction rate of 2,4-D significantly. It was found that chloride or bicarbonate ions slowed down the photo-degradation rate of 2,4-D by scavenging hydroxyl radicals. Partial inhibition by ethanol is attributed to scavenging of the OH radicals involved in the first step of the reaction.

Photocatalytic degradation of chlorinated phenoxyacetic acids by a new buoyant titania-exfoliated graphite composite photocatalyst

A new class of floating composite photocatalysts for water purification is introduced. The composite material is comprised of exfoliated graphite support, titania photocatalyst, and sol-gel-derived methyl silicate binder. The catalyst composition was optimized for the degradation of rhodamine B dye. The photodegradation performance of the optimized catalyst was compared with supported titania film and P-25 titania suspension for the degradation of chlorophenoxyacetic acids. The photodegradation of the coated catalyst was between 50percent and 95percent of the activity of supported photocatalyst film.