28170-41-4

Usage

Type of compound

Organic compound

Common uses

Herbicide and plant growth regulator

Relation to other compounds

Closely related to diuron, a widely used herbicide

Mode of action

Inhibits photosynthesis in plants, leading to the death of unwanted vegetation

Structural feature

Presence of a 3-methylphenyl group

Effectiveness

Specific chemical properties due to the 3-methylphenyl group make it effective in controlling weed growth

Environmental impact

Toxic to aquatic life and can cause harm to the environment if not used properly

Safety precautions

Handle with caution to minimize environmental and health risks

Upstream product

• 108-44-1 1-amino-3-methylbenzene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 598-94-7 1,1-Dimethylurea 
• 108-41-8 1-chloro-3-methylbenzene 
• 591-17-3 meta-bromotoluene 
• 3085-53-8 N-formyl-m-toluidine 
• 506-59-2 N,N-dimethylammonium chloride 
• 21540-35-2 N'-(3-Methylphenyl)-N,N-dimethyl-thiourea 
• 621-29-4 3-tolyl isocyanate 
• 124-40-3 dimethyl amine 

Downstream Products

• 1150096-66-4 C₁₂H₁₆N₂O₃ 
• 91430-06-7 N’-(2,5-dimethylphenyl)-N,N-dimethylurea 
• 28170-76-5 3-(4-bromo-3-methylphenyl)-1,1-dimethylurea 
• 1220015-89-3 C₁₈H₂₀N₂O₃ 
• 621-29-4 3-tolyl isocyanate 

Relevant academic research and scientific papers

In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C-N Bond Formation

We report an efficient Buchwald-Hartwig cross-coupling reaction in alcoholic solvent, in which a low catalyst loading showed excellent performance for coupling aryl halides (I, Br, and Cl) with a broad set of amines, amides, ureas, and carbamates under mild conditions. Mechanistically speaking, in a protic and polar medium, extremely bulky biarylphosphine ligands interact with the dimeric precatalyst [Pd(π-(R)-allyl)Cl]2 to form the corresponding cationic complexes [Pd(π-(R)-allyl)(L)]Cl in situ and spontaneously. The resulting precatalyst further evolves under basic conditions into the corresponding L-Pd(0) catalyst, which is commonly employed for cross-coupling reactions. This mechanistic study highlights the prominent role of alcoholic solvents for the formation of the active catalyst.

Synthesis method of 2-alkynyl substituted indole compound

The invention discloses a synthesis method of a 2-alkynyl substituted indole derivative. The synthesis method comprises the following steps: under the actions of a rhodium catalyst, a silver additiveand an oxidant, carrying out cyclization reaction on an

Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas

A novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C-H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C-H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.

One-pot synthesis of 2,3-difunctionalized indoles: Via Rh(III)-catalyzed carbenoid insertion C-H activation/cyclization

Reported herein is the first Rh(iii)-catalyzed carbenoid insertion C-H activation/cyclization of N-arylureas and α-diazo β-keto esters. The redox-neutral reaction has the following features: good to excellent yields, broad substrate/functional group tolerance, exclusive regioselectivity, and no need for additional oxidants or additives, which render this methodology as a more efficient and versatile alternative to the existing methods for the synthesis of 2,3-difunctionalized indoles.

Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: Synthetic and mechanistic studies

Cationic palladium(II) complexes have been found to be highly reactive towards aromatic C-H activation of arylureas at room temperature. A commercially available catalyst [Pd(MeCN)4](BF4)2 or a nitrile-free cationic palladium(II) complex generated in situ from the reaction of Pd(OAc)2 and HBF4, effectively catalyzes C-H activation/cross-coupling reactions between aryl iodides, arylboronic acids and acrylates under milder conditions than those previously reported. The nature of the directing group was found to be critical for achieving room temperature conditions, with the urea moiety the most effective in promoting facile coupling reactions at an ortho C-H position. This methodology has been utilized in a streamlined and efficient synthesis of boscalid, an agent produced on the kiloton scale annually and used to control a range of plant pathogens in broadacre and horticultural crops. Mechanistic investigations led to a proposed catalytic cycle involving three steps: (1) C-H activation to generate a cationic palladacycle; (2) reaction of the cationic palladacycle with an aryl iodide, arylboronic acid or acrylate, and (3) regeneration of the active cationic palladium catalyst. The reaction between a cationic palladium(II) complex and arylurea allowed the formation and isolation of the corresponding palladacycle intermediate, characterized by X-ray analysis. Roles of various additives in the stepwise process have also been studied.

Merging C-H activation and alkene difunctionalization at room temperature: A palladium-catalyzed divergent synthesis of indoles and indolines

A palladium-catalyzed 1,2-carboamination through C-H activation at room temperature is reported for the synthesis of 2-arylindoles, and indolines from readily available, inexpensive aryl ureas and vinyl arenes. The reaction initiates with a urea-directed electrophilic ortho palladation, alkene insertion, and ?2-hydride elimination sequences to provide the Fujiwara-Moritani arylation product. Subsequently, aza-Wacker cyclization, and ?2-hydride elimination provide the 2-arylindoles in high yields. Intercepting the common -alkyl-Pd intermediate, corresponding indolines are also achieved. The indoline formation is attributed to the generation of stabilized, cationic -benzyl-Pd species to suppress ?2-hydride elimination.

Rhodium(iii)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation

A Rh(iii) catalysed amino arylation of alkynes using copper as the terminal oxidant for regeneration of the catalytically active species under aerobic conditions is described. This novel C-H activation reaction was applied to the synthesis of a wide range of substituted indoles from N-arylureas.

T-BuXPhos: A highly efficient ligand for Buchwald-Hartwig coupling in water

An efficient and versatile 'green' catalytic system for the Buchwald-Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]2 showed excellent performance for coupling arylbromides or chlorides with a large set of amines, amides, ureas and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C) and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis. the Partner Organisations 2014.

Distinct reactivity of Pd(OTs)2: The intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process. Copyright

Application of Predictive QSAR Models to Database Mining: Identification and Experimental Validation of Novel Anticonvulsant Compounds

We have developed a drug discovery strategy that employs variable selection quantitative structure-activity relationship (QSAR) models for chemical database mining. The approach starts with the development of rigorously validated QSAR models obtained with