877179-04-9

Basic information

• Product Name: 2-(3,4-Dichlorophenyl)-4-fluoroaniline
• Synonyms: 2-(3,4-Dichlorophenyl)-4-fluoroaniline;3',4'-Dichloro-5-fluorobiphenyl-2-amine;3',4'-dichloro-5-fluoro-[1,1'-biphenyl]-2-aMine;[1,1']-biphenyl-2-aMine-3',4'-dichloro-5-fluoro
• CAS NO: 877179-04-9
• Molecular Formula: C₁₂H₈Cl₂FN
• Molecular Weight: 256.1030232
• Mol File: 877179-04-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 357℃ at 101.3kPa
• Appearance: /
• Density: 1.47 at 20℃
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(3,4-Dichlorophenyl)-4-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-Dichlorophenyl)-4-fluoroaniline(877179-04-9)
• EPA Substance Registry System: 2-(3,4-Dichlorophenyl)-4-fluoroaniline(877179-04-9)

Safety Data

• Hazardous Substances Data: 877179-04-9(Hazardous Substances Data)

Usage

General Description

2-(3,4-Dichlorophenyl)-4-fluoroaniline is a chemical compound with the molecular formula C12H8Cl2FN. It is a derivative of aniline, a common precursor to many dyes and pharmaceuticals. This particular compound is a substituted aniline, with two chlorine atoms attached to the phenyl ring and a fluorine atom attached to the para position. It is commonly used in the synthesis of various pharmaceuticals and agrochemicals, and can also be used as an intermediate in the production of dyes and pigments. The compound is considered to be of moderate toxicity and should be handled with care, as prolonged or excessive exposure can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 
• 151169-75-4 3,4-dichlophenylboronic acid 
• 95-76-1 m,p-dichloroaniline 
• 371-40-4 4-fluoroaniline 
• 92449-40-6 potassium 5-fluoro-2-nitrobenzoate 
• 18282-59-2 4-bromo-1,2-dichlorobenzene 
• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 2106-02-7 2-chloro-4-fluoroaniline 
• 79175-35-2 3,4-dichlorophenylmagnesium bromide 
• 405-02-7 1,2-dichloro-4-diazoniumbenzene tetrafluoroborate 
• 13124-18-0 3,4-dichlorophenylhydrazine 
• 1416964-70-9 C₆H₃Cl₂N₂O^(1-)*Na⁽¹⁺⁾ 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 877179-08-3 N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-2,2-dimethyl-propionamide 

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 articles and documents

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.

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.