612-01-1

Usage

Appearance

White, crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Use as a building block

For various organic syntheses

Use as a reagent

Preparation of various organic compounds

Potential biological activities

Antimicrobial, antiviral

Applications

Manufacture of pharmaceuticals, agrochemicals

Ongoing research and development

Yes

Upstream product

• 423-38-1 1,2,4,4-tetrachlorohexafluorobutane 
• 2645-41-2 1-Methyl-1,3,5-triphenyl-biuret 
• 307-26-6 1,1,3,5,6-pentachloro-1,2,2,3,4,4,5,6,6-nonafluoro-hexane 
• 83-01-2 diphenylcarbamic chloride 
• 5416-30-8 N,N'-diphenyl-S-methyl isothiourea 
• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 
• 62-53-3 aniline 
• 7597-36-6 N-carbamimidoyl-N'-phenyl-urea; nitrate 
• 100-61-8 N-methylaniline 
• 201230-82-2 carbon monoxide 
• 4960-31-0 Tris(methylphenylamino)methan 
• 102-07-8 bis(diphenyl)urea 
• 103-70-8 Formanilid 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 103-71-9 phenyl isocyanate 
• 100-61-8 N-methylaniline 
• 52072-98-7 N-methyl-N,N'-diphenyl-carbamimidoyl chloride 
• 2645-41-2 1-Methyl-1,3,5-triphenyl-biuret 
• 53463-31-3 N,N-Di-sek.-butyl-N'-phenyl-harnstoff 
• 93-61-8 N-methyl-N-phenylformamide 
• 121-69-7 N,N-dimethyl-aniline 
• 62-53-3 aniline 
• 23996-36-3 1-methyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 14813-85-5 1-phenyl-1,3-dihydrobenzoimidazol-2-one 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Cp2TiCl2-CATALYZED REACTION OF GRIGNARD REAGENTS WITH ISOCYANATES, FORMATION OF REDUCTION-COUPLING PRODUCT OF ISOCYANATES

Phenylisocyanate and phenylthioisocyanate react with Grignard reagents in the presence of a small amount of Cp2TiCl2 at room temperature to afford reduction-coupling products, N-methyl-N,N'-diphenylurea and N-methyl-N,N'-diphenylthiourea.

Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions

Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.

2,2,2-Trifluroenthanol promoted synthesis of unsymmetrical ureas from dioxazolones and amines via tandem lossen rearrangement/condensation process

A 2,2,2-trifluroenthanol (TFE) promoted synthesis of unsymmetric ureas was described. This approach enabled the construction of a variety of ureas from the readily prepared and easy-to-handle dioxazolones and amines via tandem Lossen rearrangement/condensation process. The reaction featured mild conditions for the urea synthesis under metal-free conditions, which was successively applied in the scale-up synthesis of herbicides Monuro and Isoproturon.

Preparation method of amide derivative

The invention provides a preparation method of an amide derivative. The method comprises the following steps: taking hydroxamic acid and an amine or thiol compound as raw materials, sequentially adding alkali and a solvent, carrying out a reaction for 2-7 hours at the temperature of 25-50 DEG C in an SO2F2 atmosphere, and after the reaction is finished, carrying out aftertreatment on a reaction solution to obtain the asymmetric urea compound or thiocarbamate compound. According to the invention, cheap, easily available and environment-friendly SO2F2 is used as an accelerant to efficiently promote the generation of isocyanate intermediates and form C-N and C-S bonds. The generation of isocyanate avoids the use of a large amount of halogen or azide dangerous reagents, so that the compound can be used as a green substitute for standard treatment conditions in Curtius rearrangement and Hofmann rearrangement reactions. The substrate is wide in applicability, and the corresponding asymmetricurea and thiocarbamate compounds can be obtained at a relatively good yield. The operation process is simple and suitable for large-scale preparation.

A Novel C–N Migration Rearrangement Based on N–F Compounds for the Synthesis of N-Alkyl Diaryl Ureas

A novel rearrangement reaction based on the structure of N-fluoro-N-(phenylsulfonyl) benzamides (FPSBA) was developed. In the presence of base, unsymmetrical N-alkyl diaryl ureas were obtained in good yields which were accomplished through secondary alkyl phenylamines initiated 1,2-phenyl-shift migration rearrangement of N-fluoro-N-(phenylsulfonyl) benzamides. The reaction was carried out without using traditional, highly toxic reagents and noble metals. Whereas without rearrangement occurrence for primary phenylamines and aliphatic amines, normal amides and N-(phenylsulfonyl) benzamides were afforded respectively. Nitrene and phenyl isocyanate included process were prevented and a secondary alkyl phenylamine initiated vicinal SN2' reaction occurred. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operation, and useful products.

An efficient one-pot synthesis of N,N′-disubstituted phenylureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid

We have developed an efficient one-pot method for the microwave-assisted synthesis of ureas and carbamates via a proposed Lossen rearrangement. Herein we report the first examples of the direct conversion of benzoyl chlorides into N,N′-disubstituted ureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid as reagent. Using our general method, we have produced 11 examples of N,N′-disubstituted phenylureas in yields up to 95% using various substituted anilines, and primary and secondary amines. Additionally, we were able to generate a series of N-aryl carbamates in moderate yields using primary, secondary and tertiary alcohols.

A Palladium-Catalyzed Domino Procedure for the Synthesis of Unsymmetrical Ureas

A palladium-catalyzed carbonylative procedure for the synthesis of unsymmetrical ureas has been developed. This one-pot one-step cascade procedure is consisted by three individual processes: carbonylation, Curtius rearrangement, and nucleophilic addition. A series of unsymmetrical ureas were prepared from easily available aryl iodides and amines in moderate to excellent yields. This procedure provides a convenient and practical approach for unsymmetrical urea synthesis. (Figure presented.).

I2-Mediated transition-metal-free aromatic C-H amination for the synthesis of benzimidazol-2-ones and related heterocycles

A practical iodine-mediated direct aromatic C-H amination reaction has been established for benzimidazol-2-one synthesis under transition-metal-free conditions. The required 1,3-diarylurea substrates are readily accessible by the addition of N-substituted arylamines to the corresponding isocyanates. This versatile and operationally simple synthetic process is broadly applicable to a wide range of 1,3-diarylureas and provides facile access to benzimidazol-2-ones and related heterocycles. Moreover, the present C-H amination reaction can also be performed directly from disubstituted amines and isocyanates without the purification of the urea intermediates in a scalable fashion.

Synthesis of ureas in the bio-alternative solvent Cyrene

Cyrene as a bio-alternative solvent: a highly efficient, waste minimizing protocol for the synthesis of ureas from isocyanates and secondary amines in the bio-available solvent Cyrene is reported. This method eliminated the use of toxic solvents, such as

Hydroxoiridium-Catalyzed Hydroalkylation of Terminal Alkenes with Ureas by C(sp3)?H Bond Activation

Direct alkylation of a methyl group, on di- and trisubstituted ureas, with terminal alkenes by C(sp3)?H bond activation proceeded in the presence of a hydroxoiridium/bisphosphine catalyst to give high yields of the corresponding addition products. The hydroxoiridium/bisphosphine complex generates an amidoiridium intermediate by reaction with ureas having an N?H bond.