2298-28-4

Usage

Chemical Class

Urea derivatives

Structure

Consists of two phenolic groups and one urea group

Applications

a. Synthesis of functional materials and pharmaceuticals
b. Production of crosslinking agents for polymers
c. Manufacturing of dyes and other organic compounds
d. Potential use as a corrosion inhibitor in industrial applications

Biological Activities

a. Antioxidant properties
b. Anti-inflammatory properties
c. Antineoplastic properties

Versatility

Diverse applications in various industries

Upstream product

• 123-30-8 4-amino-phenol 
• 57-13-6 urea 
• 1540-28-9 ethyl 2-propylacetoacetate 
• 67-56-1 methanol 
• 100-02-7 4-nitro-phenol 
• 201230-82-2 carbon monoxide 
• 105-45-3 acetoacetic acid methyl ester 
• 23159-72-0 p-hydroxyphenyl isocyanate 
• 64-17-5 ethanol 
• 123-51-3 i-Amyl alcohol 
• 71-36-3 butan-1-ol 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 124-38-9 carbon dioxide 
• 1473-33-2 1,3-bis-(4-hydroxy-phenyl)-thiourea 

Downstream Products

• 121809-87-8 2-{4-[3-(4-Hydroxy-phenyl)-ureido]-phenoxy}-2-methyl-propionic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Aerobic Oxidative Carbonylation of Amines Enables the Synthesis of Unsymmetrical N,N′-Disubstituted Ureas

A ligand-free palladium-catalyzed aerobic oxidative carbonylation of amines for the synthesis of ureas, particular unsymmetrically N,N′-disubstituted ureas, which cannot be accessed by any other palladium-catalyzed oxidative carbonylation of amines to date, is presented. An array of symmetrical and unsymmetrical ureas were straightforwardly synthesized by using inexpensive, readily available, stable, and safe amines with good to excellent yields under a pressure of 1 atm. This novel method employs oxygen as the sole oxidant and offers an attractive alternative to transition-metal-based oxidant systems.

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3

Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.

Simple preparation method of N-acyl compound

The invention relates to a simple preparation method of an N-acyl compound. The simple preparation method comprises the specific steps that an amine compound and R-OCF3 are mixed in a solvent and react for 1 min-48 h at -80-100 DEG C, after the reaction is completed, water is added for quenching, and column separation and purification or recrystallization and purification are carried out to obtainthe N-acyl compound. According to the simple preparation method of the N-acyl compound, the characteristic that a substance containing trifluorooxygen groups can be decomposed in situ to produce fluorophosgene is utilized, and the substance directly reacts with the amine compound to achieve rapid N-carbonylation of an amines substrate and efficiently prepare a urea derivative and a carbamyl fluoride compound. The simple preparation method of the N-acyl compound has the advantages that the operation is simple, the reaction time is short, the application range of the substrate is wide, no catalysts or additives need to be used, the raw materials are easy to obtain, the product yield is high, the purification is easy, and the required compound can be obtained by using a column chromatographyisolation method or recrystallization.

Co(acac)3/BMMImCl as a base-free catalyst system for clean syntheses of N,N′-disubstituted ureas from amines and CO2

A base-free catalyst system Co(acac)3/BMMImCl was developed for the carbonylation of amines with CO2. 45%2-81% isolated yields for N,N-dialkylureas and 6%2-23% isolated yields for N,N-diarylureas were obtained. The catalyst system was recovered and reused without significant loss in activity. In this catalyst system, the base catalyst and chemical dehydrant were efficiently avoided. Different reaction conditions were also discussed and a postulated mechanism was proposed.

Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates

The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.

Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas

Symmetrical 1,3-disubstituted ureas and symmetrical thioureas have been synthesized from corresponding isocyanates, diisocyanates, and isothiocyanates by a new versatile, simple, and quick method in the presence of tertiary amines at room temperature. The method under discussion has several advantages over the existing techniques, as it is simple to carry out, does not require complicated equipment, has a simple workup, and does not use expensive chemicals. Moreover, the yields are almost quantitative. This method has potential in commercial applications. Copyright Taylor & Francis, Inc.

Mo-ZrO2 solid acid catalyst for synthesis of substituted diphenylureas

Synthesis of substituted diphenylureas from substituted anilines and β- ketoester by using an efficient eco-friendly Mo-ZrO2 solid acid catalyst is described.

CARBONYLATIVE REDUCTION OF NITROPHENOLS TO AMINOPHENOLS

Two- or three-component catalysts composed of (i) sulfur or sulfur compound (H2S, CS2, COS, Na2S), (ii) basic additive (triethylamine, CH3ONa, Na2S), and usually (iii) vanadium(V) compounds (e.g.NH4VO3) were found to catalyze efficiently the reaction of CO + H2O with isomeric nitrophenols to give the corresponding aminophenols.The reaction proceeds smoothly at 398 and 483 K and initial pressure of 7 MPa, and its rate increases from 2- to 4-nitrophenol.The selectivity to aminophenols exceeding 96 per cent was obtained at the water to nitrophenol molar ratio higher than 5.The solvents such as methanol and dioxane ensured better contact of the reactants, which was necessary for achievement of such a high selectivity.The effectiveness of the sulfur components (based on the S content) is expressed by the following sequence: S : CS2 : Na2S : H2S : COS = 1 : 1.2 : 2.5 : 10 : 11.The reaction takes place also under the reduced CO pressure to 0.1 - 0.35 MPa.Formation of side products and mechanism of the reaction are discussed.