29003-72-3

Basic information

• Product Name: 3-(3,4-dimethylphenyl)-1,1-dimethylurea
• Synonyms: 3-(3,4-Dimethylphenyl)-1,1-dimethylurea; urea, N'-(3,4-dimethylphenyl)-N,N-dimethyl-
• CAS NO: 29003-72-3
• Molecular Formula: C₁₁H₁₆N₂O
• Molecular Weight: 192.2575
• Mol File: 29003-72-3.mol

Chemical Properties

• Boiling Point: 357.9°C at 760 mmHg
• Flash Point: 170.3°C
• Density: 1.075g/cm³
• Vapor Pressure: 2.64E-05mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 3-(3,4-dimethylphenyl)-1,1-dimethylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4-dimethylphenyl)-1,1-dimethylurea(29003-72-3)
• EPA Substance Registry System: 3-(3,4-dimethylphenyl)-1,1-dimethylurea(29003-72-3)

Safety Data

• Hazardous Substances Data: 29003-72-3(Hazardous Substances Data)

Upstream product

• 95-64-7 4-amino-o-xylene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 1332358-83-4 C₁₄H₂₀N₂O₃ 

Relevant articles and documents

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.

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.