581809-46-3

Basic information

• Product Name: Bixafen|
• Synonyms: N-(3',4'-Dichloro-5-fluoro-1,1'-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
• CAS NO: 581809-46-3
• Molecular Formula: C₁₈H₁₂Cl₂F₃N₃O
• Molecular Weight: 414.2085896
• Mol File: 581809-46-3.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 474.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: 10.82±0.70(Predicted)
• CAS DataBase Reference: Bixafen|(CAS DataBase Reference)
• NIST Chemistry Reference: Bixafen|(581809-46-3)
• EPA Substance Registry System: Bixafen|(581809-46-3)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 581809-46-3(Hazardous Substances Data)

Usage

Definition

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid with the amino group of 3',4'-dichloro-5-fluorobiphenyl-2-amine. A fungicide for use in cereals for key stem and leaf disease co trol including strobilurin-resistant septoria.

Upstream product

• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 
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• 151169-75-4 3,4-dichlophenylboronic acid 
• 176969-34-9 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 151733-96-9 ethyl 3-(difluoromethyl)-1H-pyrazole-4-carboxylate 
• 877179-04-9 3′,4′-dichloro-5-fluorobiphenyl-2-amine 
• 405-02-7 1,2-dichloro-4-diazoniumbenzene tetrafluoroborate 
• 371-40-4 4-fluoroaniline 
• 1416964-70-9 C₆H₃Cl₂N₂O^(1-)*Na⁽¹⁺⁾ 
• 95-76-1 m,p-dichloroaniline 
• 141573-95-7 ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 131112-05-5 bis(3,4-dichlorophenyl)borinic acid 
• 581809-55-4 N-(2-bromo-4-fluorophenyl)-1-methyl-3-(difluoromethyl)-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.

PRODUCTION METHOD FOR PYRAZOLE-4-CARBOXAMIDE DERIVATIVE

The present invention relates to a method of producing a pyrazole-4-carboxamide derivative including subjecting a pyrazole-4-carboxylic acid ester and an amine to an aminolysis reaction in a solvent in the presence of a base, provided that the reaction is

PROCESS FOR THE MANUFACTURE OF PYRAZOLE CARBOXYLIC DERIVATIVES AND PRECURSORS THEREOF

The present invention concerns processes for the manufacture of pyrazole carboxylic derivatives and precursors thereof.