587-34-8

Basic information

• Product Name: 1-(m-chlorophenyl)-3,3-dimethyl-ure
• Synonyms: 1-(m-chlorophenyl)-3,3-dimethyl-ure;1-(m-Chlorophenyl)-3,3-dimethylurea;1-(m-chlorophenyl)-3,3-dimethyl-Urea;N,N-Dimethyl-N'-(3-chlorophenyl)-urea;3-(3-Chlorophenyl)-1,1-dimethylurea;C-2034;N'-(3-Chlorophenyl)-N,N-dimethylurea
• CAS NO: 587-34-8
• Molecular Formula: C₉H₁₁ClN₂O
• Molecular Weight: 198.65
• Mol File: 587-34-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 1.8-144.3 °C
• Boiling Point: 356.8°C at 760 mmHg
• Flash Point: 169.6°C
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 2.85E-05mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.42±0.70(Predicted)
• CAS DataBase Reference: 1-(m-chlorophenyl)-3,3-dimethyl-ure(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(m-chlorophenyl)-3,3-dimethyl-ure(587-34-8)
• EPA Substance Registry System: 1-(m-chlorophenyl)-3,3-dimethyl-ure(587-34-8)

Safety Data

• Hazardous Substances Data: 587-34-8(Hazardous Substances Data)

Usage

Description

1-(m-chlorophenyl)-3,3-dimethyl-ure, also known as 3-(3-Chlorophenyl)-1,1-dimethylurea, is an organic compound with the molecular formula C9H10ClN2O. It is a derivative of phenylurea, which is characterized by the presence of a chlorophenyl group and two methyl groups attached to the urea moiety. 1-(m-chlorophenyl)-3,3-dimethyl-ure has been studied for its potential applications in various fields due to its unique chemical structure and properties.

Uses

1. Used in Agricultural Chemistry:
1-(m-chlorophenyl)-3,3-dimethyl-ure is used as a photosystem II inhibitor for [application reason] the development of herbicides. It has been studied for its quantitative structure-activity relations, which helps in understanding how the compound interacts with the Hill inhibitory activity in plants. This knowledge aids in the design and synthesis of more effective and selective herbicides.
2. Used in Environmental Science:
1-(m-chlorophenyl)-3,3-dimethyl-ure is utilized as a component in the development of a simple and rapid screening method for photosystem II inhibitory herbicides. This method employs photoautotrophically cultured plant cells with chlorophyll fluorescence monitoring, which allows for the efficient assessment of the herbicidal activity of the compound and its potential impact on the environment.

InChI:InChI=1/C9H11ClN2O/c1-12(2)9(13)11-8-5-3-4-7(10)6-8/h3-6H,1-2H3,(H,11,13)

Upstream product

• 124-40-3 dimethyl amine 
• 2909-38-8 m-chlorophenyl isocyanate 
• 201230-82-2 carbon monoxide 
• 108-42-9 3-chloro-aniline 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 50699-50-8 phenyl N-(3-chlorophenyl)carbamate 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 124-40-3 dimethyl amine 
• 2909-38-8 m-chlorophenyl isocyanate 
• 1182602-45-4 butyl (E)-3-(4-chloro-2-(3,3-dimethylureido)phenyl)acrylate 
• 15441-93-7 N’-(5-chloro-2-methyphenyl)-N,N-dimethylurea 
• 32233-73-1 3-(4-bromo-3-chlorophenyl)-1,1-dimethylurea 

Relevant articles and documents

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.

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.

THERMAL DECOMPOSITION OF SUBSTITUTED UREAS

The thermal dissociation of N,N'-diaryl- and N,N-dimethyl-N'-aryl-ureas was investigated under isothermal conditions in absence of solvent.In the case of N,N-dimethyl-N'-arylureas enthalpies of reaction were determined, and their relation to Hammett ? constants was shown.