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Basic Information
| CAS No.: | 210631-68-8 |
|---|---|
| Name: | TOPRAMEZONE |
| Article Data: | 12 |
| Molecular Structure: | |
|
|
|
| Formula: | C16H17N3O5S |
| Molecular Weight: | 363.394 |
| Synonyms: | bas 670;Hsdb 7500;TOPRAMEZONE;Topramezone [iso];[3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone; |
| Density: | 1.492g/cm3 |
| Boiling Point: | 590.491°C at 760 mmHg |
| Flash Point: | 310.918°C |
| Hazard Symbols: |
 T N
|
| Risk Codes: | 61-50/53 |
| Safety: | 53-45-60-61 |
| Transport Information: | UN3077 9/PG 3 |
| PSA: | 119.23000 |
| LogP: | 1.70940 |
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Synthetic route
- 123-91-1
1,4-dioxane
- 247922-29-8
3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole
- 33641-15-5
1-methyl-5-hydroxypyrazole
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| With carbon monoxide; potassium carbonate; triethylamine; triphenylphosphine; palladium(II) chloride In water | 100% |
| With hydrogenchloride; potassium carbonate; triethylamine; bis(triphenylphosphine)palladium(II) dichloride In water |
...Expand
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| With hydrogen bromide; methyl(tri-n-octyl)ammonium bromide for 3h; Reagent/catalyst; Reflux; | 93.5% |
- 247922-29-8
3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole
- 2597-44-6
formyl radical
- 33641-15-5
1-methyl-5-hydroxypyrazole
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole With potassium carbonate In 1,4-dioxane Reflux; Stage #2: 1-methyl-5-hydroxypyrazole With triphenylphosphine; sodium iodide In 1,4-dioxane at 60℃; for 0.5h; Stage #3: formyl radical With palladium on activated charcoal In 1,4-dioxane at 120℃; under 11251.1 Torr; for 20h; Reagent/catalyst; Temperature; | 84.4% |
...Expand
- 223646-24-0
3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid
- 33641-15-5
1-methyl-5-hydroxypyrazole
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid With pyridine; thionyl chloride In benzene for 3h; Reflux; Stage #2: 1-methyl-5-hydroxypyrazole With triethylamine In 1,4-dioxane at 20℃; for 3h; Stage #3: With potassium carbonate for 6h; Reflux; | 81.46% |
| Stage #1: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid With pyridine; thionyl chloride In toluene for 3h; Reflux; Stage #2: 1-methyl-5-hydroxypyrazole With triethylamine In 1,4-dioxane at 20℃; for 3h; | 80.5% |
| Stage #1: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid With thionyl chloride for 2h; Reflux; Stage #2: With triethylamine In 1,2-dichloro-ethane at 20 - 30℃; for 0.5h; Stage #3: 1-methyl-5-hydroxypyrazole In 1,2-dichloro-ethane for 4h; Reflux; | 20.87% |
- 247922-29-8
3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole
- 201230-82-2
carbon monoxide
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate; triethylamine; triphenylphosphine; palladium dichloride In 1,4-dioxane at 130℃; under 7500.75 Torr; for 10h; Inert atmosphere; | 70% |
...Expand
- 223646-31-9
3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride
- 75-86-5
2-hydroxy-2-methylpropanenitrile
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine In methanol; chloroform |
...Expand
- 247922-29-8
3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole
- 201230-82-2
carbon monoxide
- 33641-15-5
1-methyl-5-hydroxypyrazole
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate; triphenylphosphine; palladium dichloride In 1,4-dioxane at 130℃; under 11251.1 Torr; |
...Expand
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1.1: thionyl chloride / toluene / Reflux 1.2: 5 h / 0 °C 2.1: magnesium / tetrahydrofuran / 5 h / 60 °C / Inert atmosphere 2.2: 1 h / 10 °C / Inert atmosphere 3.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide; acetic acid / 3 h / 60 °C 4.1: methyl(tri-n-octyl)ammonium bromide; hydrogen bromide / 3 h / Reflux View Scheme |
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 5 h / 60 °C / Inert atmosphere 1.2: 1 h / 10 °C / Inert atmosphere 2.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide; acetic acid / 3 h / 60 °C 3.1: methyl(tri-n-octyl)ammonium bromide; hydrogen bromide / 3 h / Reflux View Scheme |
- 250592-91-7
3-((2-methyl)-6-methylthiophenyl)-4,5-dihydroisoxazole
- 210631-68-8
topramezone
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / ethyl acetate; hexane / 3 h / 0 °C / Reflux 1.2: 2 h / 0 - 20 °C 2.1: acetic acid; dihydrogen peroxide / 30 h / 30 °C 3.1: pyridine; thionyl chloride / toluene / 3 h / Reflux 3.2: 3 h / 20 °C View Scheme |
