95-77-2

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dichlorophenol is used as a key intermediate in the synthesis of (Z)-5-arylmethylene rhodanines, which are compounds with anti-methicillin-resistant Staphylococcus aureus (MRSA) properties. This makes it a valuable component in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Pain Management:
3,4-Dichlorophenol is also utilized in the preparation of 2-(3,4-dichlorophenoxy)-N-(2-morpholin-4-ylethyl)acetamide, a compound with potential therapeutic applications in the treatment of inflammatory pain. This highlights its role in the development of novel pain relief medications.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3,4-Dichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents.

Fire Hazard

Flash point data for 3,4-Dichlorophenol are not available. 3,4-Dichlorophenol is probably combustible.

Purification Methods

Crystallise 3,4-dichlorophenol from pet ether/*benzene mixture and/or distil it. [Beilstein 6 IV 952.]

InChI:InChI=1/C6H4Cl2O/c7-5-2-1-4(9)3-6(5)8/h1-3,9H

Upstream product

• 1435-49-0 3,4-dichlorofluorobenzene 
• 124-41-4 sodium methylate 
• 40140-91-8 3-chloro-4-nitrosophenol 
• 20555-91-3 3,4-dichloroiodobenzene 
• 95-76-1 m,p-dichloroaniline 
• 79435-99-7 5,6-Dichlorcyclohexan-3,5-dien-1,2-diol 
• 95-50-1 1,2-dichloro-benzene 
• 7664-93-9 sulfuric acid 
• 288-32-4 1H-imidazole 
• 17847-51-7 3,4-dichlorophenyl acetate 
• 108-43-0 3-monochlorophenol 
• 402-45-9 4-hydroxybenzotrifluoride 
• 1095223-19-0 1-(2-fluoro-pyridin-3-yl)-2-(3,4-dichloro-phenoxy)-ethanone 
• 319-94-8 (36/45)-1,3,4,5,6-pentachlorocyclohexene 

Downstream Products

• 81-54-9 1,2,4-trihydroxy-9,10-anthraquinone 
• 81-53-8 2-chloro-1,4-dihydroxy-9,10-anthraquinone 
• 55-11-8 4,4',5,5'-tetrachloro-2,2'-methylenebisphenol 
• 71643-64-6 3,4-dichloro-2,6-bis-hydroxymethyl-phenol 
• 3284-81-9 3-(3,4-dichlorophenoxy)propanoic acid 
• 15950-66-0 2,3,4-trichlorophenol 
• 64673-07-0 2-(3,4-dichloro-phenoxy)-ethanol 
• 54852-69-6 1-(3,4-dichloro-phenoxy)-propan-2-ol 
• 13664-64-7 2,6-dibromo-3,4-dichloro-phenol 
• 65152-06-9 3,4-dichloro-2-nitro-phenol 
• 120161-30-0 4,5-dichloro-2-hydroxy-benzenesulfonic acid 
• 5136-30-1 4,5,4',5'-tetrachloro-2,2'-sulfanediyl-di-phenol 
• 95-95-4 2,4,5-trichlorophenol 
• 62855-72-5 ethyl 2-(3,4-dichlorophenoxy)acetate 

Relevant academic research and scientific papers

Electrophotocatalytic C?H Heterofunctionalization of Arenes

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.

A dichlorophenol synthesis method (by machine translation)

The present invention provides a kind of dichlorophenol synthetic method, comprises the following steps: S1, will be 1, 4 - dichlorobenzene alkylation reaction, to obtain the 1, 4 - dichloro - 2 - isopropyl benzene; or the 1, 3 - dichlorobenzene alkylation reaction, to obtain the 1, 3 - dichloro - 4 - cumene; or the 1, 2 - dichlorobenzene alkylation reaction, to obtain 1, 2 - dichloro - 4 - cumene; S2, to the 1, 4 - dichloro - 2 - cumene in alkyl, 1, 3 - dichloro - 4 - cumene in alkyl or 1, 2 - dichloro - 4 - alkyl in the cumene, through oxidation, the formula x structure obtained dichloro peroxide; S3, will the catalytic decomposition of the peroxide states two chlorine respectively, to obtain the dichlorophenol and acetone. The present invention provides a method for synthesizing of the dichlorophenol obtained the product content is high, the three waste less generation, mild reaction conditions, easy operation, low production cost. (by machine translation)

A new process to prepare 3,6-dichloro-2-hydroxybenzoic acid, the penultimate intermediate in the synthesis of herbicide dicamba

Glyphosate [N-(phosphonomethyl)glycine] is a broad spectrum, post-emergent herbicide that is among the most widely used agrochemicals globally. Over the past 30 years, there has been a development of glyphosate-resistant weeds, which pose a significant challenge to growers and crop scientists, resulting in lower crop yields and increased costs. 3,6-Dichloro-2-methoxybenzoic acid (dicamba) is the active ingredient in XtendiMax a standalone herbicide developed by Bayer Crop Science to control broadleaf weeds, including glyphosate-resistant species. 3,6-Dichloro-2-hydroxybenzoic acid (3,6-DCSA) is the penultimate intermediate in the synthesis of dicamba. Existing dicamba manufacturing routes utilize a high temperature, high pressure Kolbe-Schmitt carboxylation to prepare 3,6-DCSA. Described in this Letter is a new, non-Kolbe-Schmitt process to prepare 3,6-DCSA from salicylic acid in four chemical steps.

Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications

An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.

Electrochemical Hydroxylation of Arenes Catalyzed by a Keggin Polyoxometalate with a Cobalt(IV) Heteroatom

The sustainable, selective direct hydroxylation of arenes, such as benzene to phenol, is an important research challenge. An electrocatalytic transformation using formic acid to oxidize benzene and its halogenated derivatives to selectively yield aryl formates, which are easily hydrolyzed by water to yield the corresponding phenols, is presented. The formylation reaction occurs on a Pt anode in the presence of [CoIIIW12O40]5? as a catalyst and lithium formate as an electrolyte via formation of a formyloxyl radical as the reactive species, which was trapped by a BMPO spin trap and identified by EPR. Hydrogen was formed at the Pt cathode. The sum transformation is ArH+H2O→ArOH+H2. Non-optimized reaction conditions showed a Faradaic efficiency of 75 % and selective formation of the mono-oxidized product in a 35 % yield. Decomposition of formic acid into CO2 and H2 is a side-reaction.

Photocatalytic benzene and benzene derivative direct hydroxylation or amination method

The invention discloses a photocatalytic benzene and benzene derivative direct hydroxylation or amination method. The method is characterized by comprising the following steps: (1) adding a photo-sensitizer and a cobalt catalyst into a solvent to obtain a solution (A); (2) adding benzene (or benzene derivatives), water, ammonia gas, and amide derivatives (or sulfonamide derivatives) into the solution (A) to obtain a solution (B); and (3) in a N2 (or Ar) environment, radiating the solution (B) by a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, or an LED lamp to obtain phenols or amines and H2. For the first time, a photo-sensitizer and a cobalt catalyst are combined and applied to photocatalytic hydroxylation and amination of benzene. The conditions of the method are mild, light is taken as the driving energy, no oxidant is added, the only byproduct is H2, and the whole process is green, concise, and efficient. High selective benzene one-step hydroxylation to generate phenol or high selective phenol/benzene one-step amination to generate aniline is realized, and the method can be applied to the production of phenol and aniline.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C-H Amination and Hydroxylation

We present a blueprint for aromatic C-H functionalization via a combination of photocatalysis and cobalt catalysis and describe the utility of this strategy for benzene amination and hydroxylation. Without any sacrificial oxidant, we could use the dual catalyst system to produce aniline directly from benzene and ammonia, and phenol from benzene and water, both with evolution of hydrogen gas under unusually mild conditions in excellent yields and selectivities.

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.

PROCESS FOR HYDROLYZING 1,2,4-TRIHALOBENZENE

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.