877179-04-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(3,4-Dichlorophenyl)-4-fluoroaniline is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(3,4-Dichlorophenyl)-4-fluoroaniline serves as a crucial component in the production of pesticides and other crop protection agents. Its chemical properties contribute to the effectiveness of these products in managing pests and diseases.
Used in Dye and Pigment Industry:
2-(3,4-Dichlorophenyl)-4-fluoroaniline is employed as an intermediate in the manufacturing process of dyes and pigments. Its presence in these compounds enhances color intensity and stability, making it valuable for various applications in textiles, plastics, and other industries.
Used in Research and Development:
2-(3,4-Dichlorophenyl)-4-fluoroaniline is also used in research and development settings to explore its potential applications and properties. Scientists and chemists investigate its reactivity, stability, and interactions with other molecules to discover new uses and improve existing processes.

Upstream product

• 131112-05-5 bis(3,4-dichlorophenyl)borinic acid 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 877179-03-8 N-(3’,4’-dichloro-5-fluorobiphenyl-2-yl)acetamide 
• 877179-08-3 N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-2,2-dimethyl-propionamide 
• 151169-75-4 3,4-dichlophenylboronic acid 
• 1416964-70-9 C₆H₃Cl₂N₂O^(1-)*Na⁽¹⁺⁾ 
• 371-40-4 4-fluoroaniline 
• 95-76-1 m,p-dichloroaniline 
• 13124-18-0 3,4-dichlorophenylhydrazine 
• 405-02-7 1,2-dichloro-4-diazoniumbenzene tetrafluoroborate 
• 19763-90-7 3,4-dichlorophenylhydrazine hydrochloride 
• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 92449-40-6 potassium 5-fluoro-2-nitrobenzoate 
• 18282-59-2 4-bromo-1,2-dichlorobenzene 

Downstream Products

• 581809-46-3 bixafen 
• 942202-47-3 N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-ethyl-1H-pyrazole-4-carboxamide 

Relevant academic research and scientific papers

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

Method for synthesizing 3, 4-dichloro-2-amino-5-fluorobiphenyl

The invention discloses a method for synthesizing 3, 4-dichloro-2-amino-5-fluorobiphenyl. The method comprises the following steps: carrying out diazotization reaction on substrate 3, 4-dichloroaniline and nitroso sulfuric acid to prepare diazonium salt; carrying out a coupling reaction on the diazonium salt and 4-fluoroaniline to obtain the product 3, 4-dichloro-2-amino-5-fluorobiphenyl; sodium chloride needing landfill treatment is not generated in the reaction process, and the method has the characteristics of mild conditions, simple operation, high raw material conversion rate and productselectivity, low energy consumption and the like, and is suitable for industrial production; byproduct sodium sulfate generated by the reaction is a brownish yellow solid; a colorless sodium sulfate product is obtained after resin adsorption decoloration and thermal evaporation concentration crystallization combined process treatment, harmless treatment and resource utilization of sodium sulfate-containing waste salt slag are realized in the whole process, the produced sodium sulfate product reaches the industrial-grade anhydrous sodium sulfate product standard, the economic benefit is improved, and the environmental pollution is avoided.

Regiospecific Introduction of Halogens on the 2-Aminobiphenyl Subunit Leading to Highly Potent and Selective M3 Muscarinic Acetylcholine Receptor Antagonists and Weak Inverse Agonists

Muscarinic M3 receptor antagonists and inverse agonists displaying high affinity and subtype selectivity over the antitarget M2 are valuable pharmacological tools and may enable improved treatment of chronic obstructive pulmonary disease (COPD), asthma, or urinary incontinence. On the basis of known M3 antagonists comprising a piperidine or quinuclidine unit attached to a biphenyl carbamate, 5-fluoro substitution was responsible for M3 subtype selectivity over M2, while 3′-chloro substitution substantially increased affinity through a σ-hole interaction. Resultantly, two piperidinyl-and two quinuclidinium-substituted biphenyl carbamates OFH243 (13n), OFH244 (13m), OFH3911 (14n), and OFH3912 (14m) were discovered, which display two-digit picomolar affinities with Ki values from 0.069 to 0.084 nM, as well as high selectivity over the M2 subtype (46-to 68-fold). While weak inverse agonistic properties were determined for the biphenyl carbamates 13m and 13n, neutral antagonism was observed for 14m and 14n and tiotropium under identical assay conditions.

Regiospecific Introduction of Halogens on the 2-Aminobiphenyl Subunit Leading to Highly Potent and Selective M3 Muscarinic Acetylcholine Receptor Antagonists and Weak Inverse Agonists

Muscarinic M3 receptor antagonists and inverse agonists displaying high affinity and subtype selectivity over the antitarget M2 are valuable pharmacological tools and may enable improved treatment of chronic obstructive pulmonary disease (COPD), asthma, or urinary incontinence. On the basis of known M3 antagonists comprising a piperidine or quinuclidine unit attached to a biphenyl carbamate, 5-fluoro substitution was responsible for M3 subtype selectivity over M2, while 3′-chloro substitution substantially increased affinity through a σ-hole interaction. Resultantly, two piperidinyl- A nd two quinuclidinium-substituted biphenyl carbamates OFH243 (13n), OFH244 (13m), OFH3911 (14n), and OFH3912 (14m) were discovered, which display two-digit picomolar affinities with Ki values from 0.069 to 0.084 nM, as well as high selectivity over the M2 subtype (46-to 68-fold). While weak inverse agonistic properties were determined for the biphenyl carbamates 13m and 13n, neutral antagonism was observed for 14m and 14n and tiotropium under identical assay conditions.

Synthesis method of bixafen

The invention relates to a synthesis method of bixafen. The method comprises the steps that firstly, 3,4-dichloroaniline is prepared into 3,4-dichloro phenylhydrazine hydrochloride through a reductionagent, then air is introduced into the 3,4-dichloro phenylhydrazine hydrochloride under an alkaline environment, the 3,4-dichloro phenylhydrazine hydrochloride and para-fluoroaniline are subjected tooxidative coupling for obtaining an intermediate 3',4'-dichloro-5-fluorine-2-benzidine, and finally the intermediate and 1-methyl-3-difluoro methyl-4-parazole formyl chloride are subjected to an amidation reaction for preparing the bixafen. According to the adopted technology, the reaction conditions are mild and easy to control, operation is easily and conveniently conducted, the product is easyto purify, and the product can be obtained directly through recrystallization. The control method for intermediates in all steps is simple and accurate, the product yield is high, the atom economy isgood, complex aftertreatment of an old method is avoided, and the method has great competitive advantages and high industry production utilization value. Meanwhile, application of raw materials, withhigh dangerousness, such as butyllithium is avoided, generation of a large amount of solid waste of tarry substances is avoided, the content of the three wastes is extremely low, and the method accords with the concept of environment-friendly chemistry.

Preparation method of 2-(3,4)-dichlorophenyl-4-fluoroaniline

The invention discloses a preparation method of 2-(3,4)-dichlorophenyl-4-fluoroaniline, comprising the steps of (1) dissolving 2-bromo-4-fluoroaniline in dichloroethane, dropwise adding acetic anhydride to obtain the compound 2-bromo-4-fluoroacetanilide; (2) dissolving the product of step (1) and 3,4-dichlorobromobenzene in an organic solvent, and dropwise adding Rieke Zn; in another reaction vessel, dissolving CuBr Sme2 in the same organic solvent, mixing, adding an oxidant for reaction, filtering the reacted liquid via silica gel, distilling in vacuum, and carrying out column chromatographyto obtain 2-(3,4-dichlorophenyl)-4-fluoroacetanilide; (3) adding the product of step (2) into the reaction vessel, adding methanol to allow full dissolution, and dropwise adding concentrated sulfuricacid slowly; when the materials completely react, pouring the mixed solution into ice water while it is hot for the purpose of quenching. A copper reagent that is low in price and easy to obtain is used to replace toxic heavy metals such as palladium; the domestic blank of studies on bixafen is filled; the foreign monopoly for bixafen is broken; progress of leaf blight and rust disease can be controlled.

A method for preparing substituted biphenyl

The invention discloses a preparation method of substituted biphenyl. The preparation method includes the steps that under the anhydrous condition, a compound 2 and a compound 3 are subjected to a coupled reaction in solvent in the presence of Ni salt and ZnX3X4, and then substituted biphenyl is obtained, wherein Ni salt is one or more of NiX5X6(PPh3)2, NiX7X8(dppp), NiX9X10(dppf), NiX11X12(dppe) and acetylacetone nickel, the temperature of the coupled reaction is 0-30 DEG C, and ZnX3X4 is mixed with the compound 3 before the compound 2 is mixed with the compound 3. According to the method, reaction conditions are mild, the process is simple, operation is safe, requirements for equipment are low, aftertreatment is simple, pollution to the environment is small, industrial production is easy, the usage quantity of zinc halides is small, the cost is low, the yield is high, and the product purity is high.

Preparation method of 3,4-dichloro-2-amino-5-fluorobiphenyl

The invention discloses a preparation method of 3,4-dichloro-2-amino-5-fluorobiphenyl, and belongs to the field of pesticide chemistry. The method is implemented by the following steps: adding 3,4-dichlorophenylboronic acid and an organic solvent into a reaction flask under the protection of nitrogen, then sequentially adding 2-bromo-4-fluoroaniline and alkali, performing heating to 70 DEG C, introducing nitrogen for protection, adding a copper catalyst, increasing the temperature to reflux, performing reaction on raw materials for 4.0 to 6.0h, and performing a post-treatment process: performing suction filtering after cooling, pouring filtrate into water, performing extraction with dichloromethane for multiple times, and performing drying and desolvation on an organic layer to obtain 3',4'-dichloro-2-amino-5-fluorobiphenyl with the content being 95.2 percent and the yield being 87.3 percent. According to the preparation method, the raw materials are simple, readily available and easyto synthesize, convenience is brought to post-treatment, and the preparation method is small in wastewater amount, relatively high in yield, and is a method suitable for preparing an intermediate 3',4'-dichloro-2-amino-5-fluorobiphenyl.

o-aminobiphenyl compound synthesis method

The invention relates to an o-aminobiphenyl compound synthesis method, which comprises: carrying out a reaction on an o-nitroaromatic formic acid compound, an alkali and a solvent, removing water, adding substituted halobenzene, a catalyst and a ligand, carrying out a reaction, or carrying out a reaction on a pre-prepared o-nitroaromatic formate, substituted halobenzene, a catalyst, a ligand and a solvent, and carrying out post-treatment to obtain the o-aminobiphenyl compound. According to the present invention, the o-aminobiphenyl compound is synthesized by using the easily available or easily prepared o-nitroaromatic formate and the substituted halobenzene as the raw material through the one-step method without the use of hydrogen and other hazardous reducing agents, such that the coupling and nitro reduction continuous reaction is achieved, and the advantages of new reaction, safety, high efficiency, simple operation and low cost are provided.

The use of the arylhydrazine synthetic amino of the biphenyl method

The present invention describes a method for synthesising 2-aminobiphenyls and derivatives thereof. This method can be performed cost-effectively and is based on selective reactions. Functionalised biphenyl compounds are of great interest, particularly as pharmaceuticals and agricultural chemicals, and as precursors for such active ingredients. The method for producing a compound of formula 3 is characterised in that a compound of formula 1 is reacted with a compound of formula 2 in the presence of an oxidising agent.