Mesotrione

Base Information

• Chemical Name: Mesotrione
• CAS No.: 104206-82-8
• Deprecated CAS: 207996-81-4,435270-61-4,435270-61-4
• Molecular Formula: C14H13NO7S
• Molecular Weight: 339.326
• Hs Code.: 2914700090
• European Community (EC) Number: 600-533-4
• UNII: 48TR68G21T
• DSSTox Substance ID: DTXSID7032424
• Nikkaji Number: J1.031.035K
• Wikipedia: Mesotrione
• Wikidata: Q409390
• Metabolomics Workbench ID: 55832
• ChEMBL ID: CHEMBL1873440
• Mol file: 104206-82-8.mol

Synonyms:(2-nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione;Callisto herbicide;mesotrione

Chemical Property of Mesotrione

Chemical Property:

• Appearance/Colour: Light yellow crystalline powder
• Vapor Pressure: 1.93E-16mmHg at 25°C
• Melting Point: 165oC
• Refractive Index: 1.583
• Boiling Point: 643.3 °C at 760 mmHg
• PKA: pKa (20°): 3.12
• Flash Point: 342.9 °C
• PSA: 139.55000
• Density: 1.474 g/cm³
• LogP: 2.72330
• Storage Temp.: 0-6°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 339.04127293
• Heavy Atom Count: 23
• Complexity: 627

Purity/Quality:

95%TC ^*data from raw suppliers

Mesotrione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Herbicides, Nitroaromatic
• Canonical SMILES: CS(=O)(=O)C1=CC(=C(C=C1)C(=O)C2C(=O)CCCC2=O)[N+](=O)[O-]
• Description: Mesotrione (2-[4-(methylsulfonyl)-2-nitrobenzoyl]-cylohexane-1,3-dione) is a selective herbicide which is also referred to as Callisto and Tenacity (trademarks). It was introduced to the market in 2001 for use in maize plantations as a control measure against grass and broad-leaved weeds. Mesotrione is a triketone herbicide which was formulated after the discovery of the naturally occurring phytotoxin leptospermone secreted by the Callistemon citrinus plant.
• Uses: Mesotrione is a herbicide that works by inhibiting 4-hydroxyphenylpyruvate dioxygenase (HPPD), a crucial enzyme for the biosynthesis of carotenoid in plants. Mesotrione is also a synthetic analog of l epospermone. Herbicide.

Technology Process of Mesotrione

There total 15 articles about Mesotrione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3-(4'-methylsulfonyl-2'-nitro-benzoyloxy)-2-cyclohexene-1-one (226944-49-6) → mesotrione (104206-82-8,435270-61-4)

Guidance literature:

With caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20 - 30 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 89.66%

4-methylsulphonyl-2-nitrobenzoyl chloride (110964-80-2) + 1,3-cylohexanedione (504-02-9) → mesotrione (104206-82-8,435270-61-4)

Guidance literature:

With triethylamine; 2-hydroxy-2-methylpropanenitrile; In dichloromethane; at 15 ℃; Large scale;

Reference yield: 80.3%

4-methanesulfonyl-2-nitro-benzoic acid (110964-79-9) + 1,3-cylohexanedione (504-02-9) → mesotrione (104206-82-8,435270-61-4)

Guidance literature:

4-methanesulfonyl-2-nitro-benzoic acid; 1,3-cylohexanedione; With dicyclohexyl-carbodiimide; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 - 150 ℃;

In 5,5-dimethyl-1,3-cyclohexadiene; acetonitrile; Solvent;

upstream raw materials:

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

1,3-cylohexanedione

1,2,4-Triazole

1-fluoro-4-methanesulfonyl-2-nitrobenzene

Downstream raw materials:

2-amino-4-(methylsulfonyl)benzoic acid

4-methanesulfonyl-2-nitro-benzoic acid

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

Refernces

• 1、 -. "Method for preparing triketone compound through continuous flow". Paragraph 0023-0025. . Retrieved 2021/09/08.
• 2、 Tang, Lili,Du, Kejie,Yu, Bing,He, Liangnian. "Oxidation of aromatic sulfides with molecular oxygen: Controllable synthesis of sulfoxides or sulfones". . p. 2991 - 2992. Retrieved 2020/03/24.