447399-55-5

Basic information

• Product Name: 3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole
• Synonyms: 447399-55-5
• CAS NO: 447399-55-5
• Molecular Formula: C₁₂H₁₄F₅N₃O₄S
• Molecular Weight: 391.3143
• Mol File: 447399-55-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 418.079°C at 760 mmHg
• Flash Point: 206.647°C
• Density: 1.598g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole(447399-55-5)
• EPA Substance Registry System: 3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole(447399-55-5)

Safety Data

• Hazardous Substances Data: 447399-55-5(Hazardous Substances Data)

Usage

General Description

3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole is a chemical compound with a complex structure that includes a sulfonyl group, a pyrazole ring, and an oxazole ring. It also contains difluoromethoxy and trifluoromethyl substituents. 3-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole is a synthetic organic molecule with potential applications in pharmaceuticals, agrochemicals, and materials science. It may have biological activity and is likely to be highly reactive due to the presence of multiple functional groups. Further research and analysis are necessary to fully understand the properties and potential uses of this chemical.

Synthetic route

3-(((5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)thio)-5,5-dimethyl-4,5-dihydroisoxazole (656825-92-2) → pyroxasulfone (447399-55-5)

Conditions	Yield
With sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide In methanol at 25℃; for 5h; Reagent/catalyst;	95%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 4h;	86%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃;	80.6%

2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol (122431-37-2) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 2.58 h / 24 °C 1.2: 16 h / 20 °C 1.3: 16 h / 14 - 20 °C 2.1: sodium hydroxide / acetonitrile / 1.67 h / 20 - 24 °C 2.2: 60.75 h / 5 - 20 °C 3.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / acetic acid / 16.33 h / 20 - 34 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 1.2: 5.33 h / 25 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 2.2: 6 h / 25 °C 3.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water; acetonitrile 2: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 0 - 25 °C 3: potassium carbonate / acetonitrile / 4 h 4: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide; formaldehyd / water / 40 °C 2: potassium hydroxide; water / acetonitrile / 25 °C 3: thionyl chloride / acetonitrile / 20 °C 4: sodium hydroxide / water / 100 °C 5: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

[5,5-dimethyl(4,5-dihydroisoxazol-3-yl)]thiocarboxamidine hydrochloride → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 2.58 h / 24 °C 1.2: 16 h / 20 °C 1.3: 16 h / 14 - 20 °C 2.1: sodium hydroxide / acetonitrile / 1.67 h / 20 - 24 °C 2.2: 60.75 h / 5 - 20 °C 3.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / acetic acid / 16.33 h / 20 - 34 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 1.2: 5.33 h / 25 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 2.2: 6 h / 25 °C 3.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

Methyl 3,3-dimethylacrylate (924-50-5) → pyroxasulfone (447399-55-5)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: N-hydroxyurea; potassium methanolate / methanol / 18.5 h / 25 °C / Inert atmosphere 2.1: phosphorus pentachloride / 1,2-dichloro-ethane / 5 h / 25 °C / Inert atmosphere 3.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 4.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 4.2: 5.33 h / 25 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 5.2: 6 h / 25 °C 6.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

5,5-dimethyl-3-isoxazolidinone (62243-00-9) → pyroxasulfone (447399-55-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: phosphorus pentachloride / 1,2-dichloro-ethane / 5 h / 25 °C / Inert atmosphere 2.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 3.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 3.2: 5.33 h / 25 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 4.2: 6 h / 25 °C 5.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

3-chloro-5,5-dimethyl-4,5-dihydroisoxazoline (326829-08-7) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 2.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 2.2: 5.33 h / 25 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 3.2: 6 h / 25 °C 4.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen bromide / isobutene / 25 - 40 °C 2: sodium hydroxide / water / 100 °C 3: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

(5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)- 1H-pyrazol-4-yl)methanol (946409-52-5) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 0 - 25 °C 2: potassium carbonate / acetonitrile / 4 h 3: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / acetonitrile / 20 °C 2: sodium hydroxide / water / 100 °C 3: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

3-bromo-5,5-dimethyl-4,5-dihydroisoxazole (882697-80-5) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide / tert-butyl alcohol 2: potassium carbonate / acetonitrile / 4 h 3: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme

4-(chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole + 5,5-dimethyl-4,5-dihydroisoxazol-3-yl carbamimidothioate hydrobromide → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 4 h 2: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme

3-[[[5-(hydroxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethylisoxazole (447402-29-1) + Chlorodifluoromethane (75-45-6) → pyroxasulfone (447399-55-5)

Conditions	Yield
Stage #1: 3-[(5-hydroxy-1-methyl-3-trifluoromethylpyrazol-4-yl)-methylthio]-4,5-dihydro-5,5-dimethylisooxazole; Chlorodifluoromethane With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Stage #2: With sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide In methanol for 6h;

potassium 4-(hydroxymethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-olate → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide; water / acetonitrile / 25 °C 2: thionyl chloride / acetonitrile / 20 °C 3: sodium hydroxide / water / 100 °C 4: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

pyroxasulfone (447399-55-5) + GLUTATHIONE (70-18-8) → C15H24N4O7S

Conditions	Yield
With TaQ8GTC1-R protein In aq. phosphate buffer; glycerol at 30℃; for 1h; pH=6.8;

Upstream product

• 924-50-5 Methyl 3,3-dimethylacrylate 
• 62243-00-9 5,5-dimethyl-3-isoxazolidinone 
• 326829-08-7 3-chloro-5,5-dimethyl-4,5-dihydroxyisoxazole 
• 447402-29-1 3-[[[5-(hydroxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethylisoxazole 
• 75-45-6 Chlorodifluoromethane 
• 882697-80-5 3-bromo-5,5-dimethyl-4,5-dihydroisoxazole 
• 946409-52-5 (5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)- 1H-pyrazol-4-yl)methanol 
• 122431-37-2 2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol 
• 656825-92-2 3-(((5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)thio)-5,5-dimethyl-4,5-dihydroisoxazole 

Relevant articles and documents

Synthesis method of sulfolazamide

The present invention discloses a method of synthesis of sulfolapriazole, 1-methyl-3-trifluoromethyl-5-hydroxy-1H-pyrazole as raw material, in the presence of an organic solvent and lye, hydroxymethylation reaction with formaldehyde to give hydroxypyrazole methanol; hydroxypyrazole methanol and difluorochloromethane for etherification reaction to give etherified pyrazole methanol; and then etherified pyrazol methanol and isoxazole urea salt and phase transfer catalyst for condensation reaction to obtain sulfur ether; the sulfur ether and hydrogen peroxide in the presence of the catalyst oxidation reaction, Get piroxazole sulfoxide. The technical route of sulfolarazole designed of the present invention is different from the existing process route, its reaction steps are short, the yield is high, the cost is low, and the hydroxymethylation, etherification and condensation reaction can be directly carried out in the same reaction flask directly in a pot reaction, more suitable for industrial production.

SOLID STATE FORM OF PYROXASULFONE

The present disclosure relates to a solid state form of Pyroxasulfone, processes for preparation thereof and agrochemical compositions thereof.

Synthesis method and application of pyroxasulfone

The invention relates to the technical field of pesticides, and provides a synthesis method of pyroxasulfone, which comprises the steps of: (1) carrying out a hydroxyalkylation reaction, a fluoromethylation reaction and a chlorination reaction on a reaction body (I) to obtain an intermediate 2; and (2) mixing an intermediate 1 and the intermediate 2, adding water to separate out an organic phase to obtain a transition intermediate, and adding a solvent and an oxidizing agent for reaction to obtain pyroxasulfone. The invention further provides application of pyroxasulfone to pesticides. The pyroxasulfone is prepared by the synthesis method. According to the invention, the overall yield of the target product can be increased, the generation of by-products can be reduced, the generation of three wastes is perfectly reduced, and the recycling of the solvent is realized.