Product Name

  • Name

    Mesotrione

  • EINECS
  • CAS No. 104206-82-8
  • Article Data22
  • CAS DataBase
  • Density 1.474 g/cm3
  • Solubility
  • Melting Point 165oC
  • Formula C14H13NO7S
  • Boiling Point 643.3 °C at 760 mmHg
  • Molecular Weight 339.326
  • Flash Point 342.9 °C
  • Transport Information UN 3077
  • Appearance Light yellow crystalline powder
  • Safety 60-61
  • Risk Codes 50/53
  • Molecular Structure Molecular Structure of 104206-82-8 (Mesotrione)
  • Hazard Symbols DangerousN
  • Synonyms Callisto;Tenacity;Tenacity (herbicide);ZA 1296;Mesotrione [ISO];EINECS Annex I Index 609-064-00-X;HSDB 7250;2-(4-Mesyl-2-nitrobenzoyl)-1,3-cyclohexanedione;
  • PSA 139.55000
  • LogP 2.72330

Synthetic route

3-(4'-methylsulfonyl-2'-nitro-benzoyloxy)-2-cyclohexene-1-one
226944-49-6

3-(4'-methylsulfonyl-2'-nitro-benzoyloxy)-2-cyclohexene-1-one

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
With caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20 - 30℃; for 2h; Reagent/catalyst; Temperature;95%
With 6-chloro-7H-purine at 60 - 65℃; for 4h;92.3%
With triethylamine; 2-hydroxy-2-methylpropanenitrile In acetonitrile at 20℃; for 10h; Inert atmosphere;54%
4-methylsulphonyl-2-nitrobenzoyl chloride
110964-80-2

4-methylsulphonyl-2-nitrobenzoyl chloride

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
With triethylamine; 2-hydroxy-2-methylpropanenitrile In dichloromethane at 15℃; Large scale;89.66%
With triethylamine In dichloromethane at 35 - 40℃;88.74%
Stage #1: 4-methylsulphonyl-2-nitrobenzoyl chloride; 1,3-cylohexanedione In dichloromethane at 15℃; for 2h;
Stage #2: With 2-hydroxy-2-methylpropanenitrile In dichloromethane at 32℃; for 3h; Temperature;		88%
Stage #1: 4-methylsulphonyl-2-nitrobenzoyl chloride; 1,3-cylohexanedione With 15-crown-5; sodium hydroxide In chloroform at 35℃; for 1.5h;
Stage #2: With 15-crown-5; sodium hydroxide; N,N,N',N'-tetramethylguanidine In chloroform at 350℃; for 3.5h; Solvent; Temperature;		88.98%
4-methanesulfonyl-2-nitro-benzoic acid
110964-79-9

4-methanesulfonyl-2-nitro-benzoic acid

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Stage #1: 4-methanesulfonyl-2-nitro-benzoic acid; 1,3-cylohexanedione With dicyclohexyl-carbodiimide In 5,5-dimethyl-1,3-cyclohexadiene at 140 - 150℃;
Stage #2: In 5,5-dimethyl-1,3-cyclohexadiene; acetonitrile Solvent;		80.3%
C14H13NO5S

C14H13NO5S

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
With diethylene glycol dibutyl ether; oxygen at 150℃; for 20h; Green chemistry;72%
With diethylene glycol dibutyl ether; oxygen at 150℃; for 20h;72%
1-(2-Nitro-4-methanesulphonylbenzoyl)-1,2,4-triazole

1-(2-Nitro-4-methanesulphonylbenzoyl)-1,2,4-triazole

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
With potassium carbonate In water; acetonitrile
1,2,4-Triazole
288-88-0

1,2,4-Triazole

3-(4'-methylsulfonyl-2'-nitro-benzoyloxy)-2-cyclohexene-1-one
226944-49-6

3-(4'-methylsulfonyl-2'-nitro-benzoyloxy)-2-cyclohexene-1-one

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
In potassium carbonate
1-fluoro-4-methanesulfonyl-2-nitrobenzene
453-72-5

1-fluoro-4-methanesulfonyl-2-nitrobenzene

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / dimethyl sulfoxide / 3 h / 310 °C
1.2: 3 h
2.1: thionyl chloride / Reflux
3.1: triethylamine / toluene / 20 - 30 °C
4.1: benzyl triethylammonium azide; triethylamine / 50 °C
View Scheme
1-chloro-4-methanesulfonyl-2-nitrobenzene
97-07-4

1-chloro-4-methanesulfonyl-2-nitrobenzene

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / dimethyl sulfoxide / 1 h / 60 °C
1.2: 2 h
2.1: thionyl chloride / Reflux
3.1: triethylamine / toluene / 20 - 30 °C
4.1: benzyl triethylammonium azide; triethylamine / 50 °C
View Scheme
4-methanesulfonyl-2-nitro-benzoic acid
110964-79-9

4-methanesulfonyl-2-nitro-benzoic acid

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / Reflux
2: triethylamine / toluene / 20 - 30 °C
3: benzyl triethylammonium azide; triethylamine / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: phosgene / toluene; N,N-dimethyl-formamide / 2 h / 70 - 80 °C
2: potassium carbonate / 8 h / 55 °C
3: 6-chloro-7H-purine / 4 h / 60 - 65 °C
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 6.5 h / 65 - 69 °C / Inert atmosphere
2: triethylamine / dichloromethane / 20 °C
3: triethylamine; 2-hydroxy-2-methylpropanenitrile / acetonitrile / 10 h / 20 °C / Inert atmosphere
View Scheme
1-methyl-4-(methylsulfonyl)-2-nitrobenzene
1671-49-4

1-methyl-4-(methylsulfonyl)-2-nitrobenzene

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: vanadia; nitric acid / 135 - 160 °C
2: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 6 h / 60 - 65 °C
3: triethylamine / 1,2-dichloro-ethane / 1 h / 5 - 35 °C
4: triethylamine; 2-hydroxy-2-methylpropanenitrile / 5 h / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: vanadia; sulfuric acid; nitric acid / 13 h / 145 - 165 °C
2.1: N,N-dimethyl-formamide / dichloromethane / 0.5 h
2.2: 5 h / 30 - 80 °C
3.1: tetrabutylammomium bromide / water; dichloromethane / 6 h / 2 °C
4.1: triethylamine / dichloromethane / 0.25 h / 30 °C
4.2: 3 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: oxygen; cobalt(II) chloride; iron(III) sulfate / acetic acid / 300 °C / 18751.9 Torr
2.1: bis(trichloromethyl) carbonate / N,N-dimethyl-formamide / 3 h / 70 °C
3.1: 15-crown-5; sodium hydroxide / chloroform / 1.5 h / 35 °C
3.2: 3.5 h / 350 °C
View Scheme
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: chlorosulfonic acid / 3.5 h / 110 - 115 °C
1.2: 3 h / 60 - 65 °C
2.1: sodium sulfite; sodium carbonate / water / 3 h / 0 - 25 °C / pH 7.5 - 8
2.2: 14 h / 40 - 100 °C
3.1: vanadia; nitric acid / 135 - 160 °C
4.1: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 6 h / 60 - 65 °C
5.1: triethylamine / 1,2-dichloro-ethane / 1 h / 5 - 35 °C
6.1: triethylamine; 2-hydroxy-2-methylpropanenitrile / 5 h / 20 - 25 °C
View Scheme
4-methyl-3-nitrobenzenesulfonyl chloride
616-83-1

4-methyl-3-nitrobenzenesulfonyl chloride

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium sulfite; sodium carbonate / water / 3 h / 0 - 25 °C / pH 7.5 - 8
1.2: 14 h / 40 - 100 °C
2.1: vanadia; nitric acid / 135 - 160 °C
3.1: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 6 h / 60 - 65 °C
4.1: triethylamine / 1,2-dichloro-ethane / 1 h / 5 - 35 °C
5.1: triethylamine; 2-hydroxy-2-methylpropanenitrile / 5 h / 20 - 25 °C
View Scheme
Methyl p-tolyl sulfone
3185-99-7

Methyl p-tolyl sulfone

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: nitric acid; sulfuric acid / 1.17 h / Large scale
1.2: 33.5 h / 142 - 146 °C / Large scale
2.1: thionyl chloride / N,N-dimethyl-formamide / Reflux; Large scale
3.1: 2-hydroxy-2-methylpropanenitrile; triethylamine / dichloromethane / 15 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid; nitric acid / 5.58 h
1.2: 142 - 145 °C
2.1: thionyl chloride / N,N-dimethyl-formamide / 65 °C
3.1: triethylamine / dichloromethane / 35 - 40 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid / 0.5 h / 20 °C
1.2: 10 h / 10 °C
2.1: vanadia; sulfuric acid; nitric acid / 13 h / 145 - 165 °C
3.1: N,N-dimethyl-formamide / dichloromethane / 0.5 h
3.2: 5 h / 30 - 80 °C
4.1: tetrabutylammomium bromide / water; dichloromethane / 6 h / 2 °C
5.1: triethylamine / dichloromethane / 0.25 h / 30 °C
5.2: 3 h / 30 °C
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

mesotrione
104206-82-8

mesotrione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate; sodium sulfite / water / 9 h / 75 °C
1.2: 4.5 h / 45 - 130 °C
2.1: sulfuric acid / 0.5 h / 20 °C
2.2: 10 h / 10 °C
3.1: vanadia; sulfuric acid; nitric acid / 13 h / 145 - 165 °C
4.1: N,N-dimethyl-formamide / dichloromethane / 0.5 h
4.2: 5 h / 30 - 80 °C
5.1: tetrabutylammomium bromide / water; dichloromethane / 6 h / 2 °C
6.1: triethylamine / dichloromethane / 0.25 h / 30 °C
6.2: 3 h / 30 °C
View Scheme
copper(II) hydroxide

copper(II) hydroxide

mesotrione
104206-82-8

mesotrione

copper chelate of 2-(2'-nitro-4'-methylsulphonylbenzoyl)-1,3-cyclohexanedione

copper chelate of 2-(2'-nitro-4'-methylsulphonylbenzoyl)-1,3-cyclohexanedione

Conditions
ConditionsYield
Stage #1: copper(II) hydroxide; mesotrione With acetic acid In water at 25 - 35℃; for 1.5 - 2h; pH=2.3 - 4.0;
Stage #2: With ammonium nitrate In water
mesotrione
104206-82-8

mesotrione

A

2-amino-4-(methylsulfonyl)benzoic acid
393085-45-5

2-amino-4-(methylsulfonyl)benzoic acid

B

4-methanesulfonyl-2-nitro-benzoic acid
110964-79-9

4-methanesulfonyl-2-nitro-benzoic acid

Conditions
ConditionsYield
With TiO2 Degussa P25; oxygen In water pH=4; Kinetics; Mechanism; Reagent/catalyst; pH-value; Wavelength; UV-irradiation;
mesotrione
104206-82-8

mesotrione

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With hematite; oxalic acid In water at 20℃; pH=4; Kinetics; Reagent/catalyst; Concentration; pH-value; UV-irradiation; Green chemistry;
mesotrione
104206-82-8

mesotrione

A

2-amino-4-(methylsulfonyl)benzoic acid
393085-45-5

2-amino-4-(methylsulfonyl)benzoic acid

B

xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl

xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl

C

2-hydroxy-4-(methylsulfonyl)-2-nitrobenzoic acid
108153-42-0

2-hydroxy-4-(methylsulfonyl)-2-nitrobenzoic acid

D

4-methanesulfonyl-2-nitro-benzoic acid
110964-79-9

4-methanesulfonyl-2-nitro-benzoic acid

Conditions
ConditionsYield
With water; copper(l) chloride for 24h; pH=6.5; Kinetics; Irradiation;
...Expand
mesotrione
104206-82-8

mesotrione

2-amino-4-(methylsulfonyl)benzoic acid
393085-45-5

2-amino-4-(methylsulfonyl)benzoic acid

Conditions
ConditionsYield
In water pH=6.5;
With nitroreductase NfrA2/YncD from Bacillus megaterium Mes11 strain, His-tagged; NADH In aq. buffer at 28℃; for 1h; pH=6.5; Enzymatic reaction;
copper(l) chloride

copper(l) chloride

mesotrione
104206-82-8

mesotrione

C14H15CuNO7S

C14H15CuNO7S

Conditions
ConditionsYield
In water pH=6.5;
copper(II) sulfate
7758-99-8

copper(II) sulfate

mesotrione
104206-82-8

mesotrione

mesotrione copper chelate

mesotrione copper chelate

Conditions
ConditionsYield
Stage #1: mesotrione With sodium hydroxide In water for 1h; pH=7- 10;
Stage #2: copper(II) sulfate In water pH=4.8-5.2; Reagent/catalyst;		555 mg
mesotrione
104206-82-8

mesotrione

C14H13NO4S

C14H13NO4S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; iron / tert-butyl methyl ether; water / 3 h / 25 - 60 °C / pH 2.5
2: water; sodium hydroxide / 0.5 h / 70 °C / pH 13.8
View Scheme
mesotrione
104206-82-8

mesotrione

C14H15NO5S

C14H15NO5S

Conditions
ConditionsYield
With hydrogenchloride; iron In tert-butyl methyl ether; water at 25 - 60℃; for 3h; pH=2.5; Solvent; Temperature; Reagent/catalyst; pH-value;

Mesotrion Chemical Properties

The Molecular Structure of 1,3-Cyclohexanedione, 2-(4-(methylsulfonyl)-2-nitrobenzoyl)- (CAS NO.104206-82-8):

Empirical Formula: C14H13NO7S
Molecular Weight: 339.3205 
IUPAC Name: 2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohexane-1,3-dione
Nominal Mass: 339 Da
Average Mass: 339.3205 Da
Monoisotopic Mass: 339.041272 Da 
Index of Refraction: 1.583
Molar Refractivity: 76.92 cm3
Molar Volume: 230 cm3
Surface Tension: 61 dyne/cm
Density: 1.474 g/cm3
Flash Point: 342.9 °C
Enthalpy of Vaporization: 94.93 kJ/mol
Boiling Point: 643.3 °C at 760 mmHg
Vapour Pressure: 1.93E-16 mmHg at 25°C 
InChI
InChI=1/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3
Smiles
C1(C(C(CCC1)=O)C(c1c(cc(cc1)S(=O)(=O)C)[N+](=O)[O-])=O)=O 
Synonyms: Mesotrione [ISO] ; EINECS Annex I Index 609-064-00-X ; HSDB 7250 ; Mesotrione ; ZA 1296

Mesotrion Safety Profile

Hazard Codes: DangerousN
Risk Statements: 50/53 
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 60-61 
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR UN: 3077
Hazardous Substances: Data 104206-82-8(Hazardous Substances Data)

Mesotrion Specification

 1,3-Cyclohexanedione, 2-(4-(methylsulfonyl)-2-nitrobenzoyl)- (CAS NO.104206-82-8) is also called as (2-Nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione . 

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