587-90-6

Usage

Uses

Used in Poultry Industry:
1,3-BIS(4-NITROPHENYL)UREA is used as an active component in the antifertility agent nicarbazin for the purpose of controlling the reproductive capabilities of chickens, ducks, and geese. This application helps in managing the population and ensuring the focus remains on the growth and health of the birds intended for consumption.
The chemical properties of 1,3-BIS(4-NITROPHENYL)UREA, such as its yellow solid state, contribute to its effectiveness in this application, allowing for easy identification and handling within the industry.

Purification Methods

Crystallise the urea from EtOH (m 364o, long heating), EtOH/Me2CO (m 301-303o, 300-304o dec, 318-319o) or Me2CO (m 289o dec). It sublimes in vacuo.[Beilstein 12 H 723, 12 II 393, 12 III 1619, 12 IV 1646.]

InChI:InChI=1/C13H10N4O5/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22/h1-8H,(H2,14,15,18)

Upstream product

• 603-54-3 N,N-diphenylurea 
• 1932-32-7 N-(4-nitrophenyl)-N'-phenylurea 
• 859807-24-2 (4-nitro-phenyl)-carbamic acid trichloromethyl ester 
• 2733-41-7 4-nitrobenzoyl azide 
• 108-24-7 acetic anhydride 
• 100-28-7 4-Nitrophenyl isocyanate 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 108-88-3 toluene 
• 100-01-6 4-nitro-aniline 
• 67-64-1 acetone 
• 75-44-5 phosgene 
• 121-69-7 N,N-dimethyl-aniline 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 4550-72-5 N,N'-bis(4-aminophenyl)urea 
• 500693-57-2 N,N'-bis-(2,4-dinitro-phenyl)-urea 
• 100-01-6 4-nitro-aniline 
• 102-07-8 bis(diphenyl)urea 
• 86488-78-0 C₁₃H₉N₅O₆ 
• 3846-49-9 1,3-diethyl-1,3-bis(4-nitrophenyl)urea 
• 34594-47-3 1,3-dimethyl-1,3-bis(4-nitrophenyl)urea 
• 6465-01-6 (4-nitrophenyl)carbamic acid phenyl ester 
• 4596-98-9 1,3-bis(2,4-dinitrophenyl)-1,3-diethylurea 
• 96615-72-4 1,3-Bis-[4-(4,6-diamino-2,2-dimethyl-2H-[1,3,5]triazin-1-yl)-phenyl]-urea; hydrochloride 
• 6410-10-2 para red 
• 6305-08-4 N,N'-dipicryl-urea 
• 1392278-33-9 methyl 3-(4-[3-(4-aminophenyl)ureido]phenylaminomethyl)benzoate 
• 31604-39-4 2-(4-nitrophenyl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Nature of urea-fluoride interaction: Incipient and definitive proton transfer

1,3-bis(4-nitrophenyl)urea (1) interacts through hydrogen bonding with a variety of oxoanions in an MeCN solution to give bright yellow 1:1 complexes, whose stability decreases with the decreasing basicity of the anion (CH 3COO- > C6H5COO- > H2PO4- > NO2- > HSO4- > NO3-). The [Bu 4N][1·CH3COO] complex salt has been isolated as a crystalline solid and its molecular structure determined, showing the formation of a discrete adduct held together by two N-H...O hydrogen bonds of moderate strength. On the other hand, the F- ion first establishes a hydrogen-bonding interaction with 1 to give the most stable 1:1 complex, and then on addition of a second equivalent, induces urea deprotonation, due to the formation of HF2-. The orange-red deprotonated urea solution uptakes carbon dioxide from air to give the tetrabutylammonium salt of the hydrogencarbonate H-bond complex, [Bu4N][1·HCO 3], whose crystal and molecular structures have been determined.

Investigation of active sites using solid state 27Al and 31P MAS NMR in ceramic amorphous aluminophosphate materials prepared from different potassium salts of phosphate for the synthesis of diphenyl urea derivatives

Ceramic amorphous aluminophosphate (CAmAlP) catalysts were prepared by precipitation method using different phosphate salts of potassium such as KH2PO4, K4P2O7 and K2HPO4 as well as H3PO4. The prepared materials were characterized by PXRD, FT-IR, XPS, SEM, BET Surface area, NH3-TPD, 27Al NMR and 31P NMR analytical methods. The catalytic activity of the materials was checked in the synthesis of diphenyl urea (DPU) from aniline and diethyl carbonate, under refluxing conditions. Further, the general application of the catalysts was tested using various substituted anilines. The recyclability of the catalysts was also studied. Uncertainties in percentage yields were calculated to check the reproducible surface properties. The P-XRD, BET Surface area and NH3-TPD results indicated that the materials were amorphous with mesoporous texture, surface areas and acidities in the range 200–260 m2/g and 0.4–0.7 mmol/g respectively. 27Al NMR studies revealed that Al is present in three different coordination states such as tetrahedral, pentagonal and octahedral. The relative percentages of these Al sites depends on the type of the potassium precursor phosphate salt used. Both tetrahedral and pentagonal Al sites in conjunction with each other represented catalytically active sites. An increase in the pentagonal sites contributed to additional increments to the catalytic activity of CAmAlP. The catalyst prepared from KH2PO4 was found to be the best and demonstrated 96% DPU yield.

Zinc Powder Catalysed Formylation and Urealation of Amines Using CO2 as a C1 Building Block?

Transformation of CO2 into valuable organic compounds catalysed by cheap and biocompatible metal catalysts is one of important topics of current organic synthesis and catalysis. Herein, we report the zinc powder catalysed formylation and urealation of amines with CO2 and (EtO)3SiH under solvent free condition. Using 2 molpercent zinc powder as the catalyst, a series of secondary amines, both the aromatic ones and the aliphatic ones, can be formylated into formamides. When primary aromatic amines were used as the substrates, the reactions produce urea derivatives. The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed. The recovery and reusability of zinc powder were investigated, showing the zinc powder can be reused in the formylation reaction without loss of catalytic activity. The analysis on the reactants/products mixture after filtering out the zinc powder showed the zinc concentration in the mixture is low to 1 ppm. The pathways for the formylation and urealation of amines with this catalytic system were also investigated, and related to the different substrates.

Method for preparing symmetric urea compound

The invention provides a novel reaction system for synthesizing a symmetric urea compound by taking CO2 as a carbonylation reagent, wherein Lewis base and hydrosilane are used as accelerators and efficiently enable an aromatic/aliphatic primary amine compound to react with normal-pressure CO2 to generate corresponding symmetric urea compounds containing different functional groups under mild conditions (100 DEG C, diglyme). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of toxic carbonylation reagents, isocyanate, high-pressure CO2, expensive dehydrating agents and precious metals is avoided, purification and separation ofintermediates are not needed, pure products can be obtained only through simple suction filtration and separation after the reaction is finished, and the method is an efficient and novel synthesis method and has high industrial application value.

Preparation method of symmetric urea compound

The invention discloses a preparation method of a symmetric urea compound, which comprises the following steps: by using a hydroxamic acid compound as a raw material, sequentially adding an alkali anda solvent, reacting at 25-50 DEG C for 1-7 hours in an SO2F2 atmosphere, and carrying out aftertreatment on the reaction solution to obtain the symmetric urea compound. According to the invention, cheap, easily available and environment-friendly SO2F2 is used as an accelerant to efficiently promote the generation of an isocyanate intermediate to form a C-N bond. 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 amine source in the final product only comes from hydroxylamine, and no additional amine needs to be added, so that the substrate is wide in applicability, and the correspondingsymmetric urea compound can be obtained at a relatively good yield. The operation process is simple, the aftertreatment only needs filtering, and the method is suitable for large-scale preparation.

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.

The: Trans / cis photoisomerization in hydrogen bonded complexes with stability controlled by substituent effects: 3-(6-aminopyridin-3-yl)acrylate case study

The association of aminopyridine-based acrylic acid and its salt was studied by NMR titration experiments. The AA (acceptor, acceptor) hydrogen-bonding pattern present in the salt forms a complex readily with a DD (donor, donor) hydrogen-bonding pattern of the substituted ureas even in polar and competitive environment. The double carbon-carbon bond in the acrylic acid derivative is subjected to photoisomerization. This is dependent on the association with substituted urea derivatives. The substituent in ureas influences the trans/cis isomerization kinetics and position of the photostationary state. Two mechanisms that influence the photoisomerization were proposed. To the best of our knowledge, the trans/cis photoisomerization influenced by the substituent in such a hydrogen-bonding pattern has not observed previously. It was shown that interaction with urea derivatives causes lowering of the trans-to-cis photoreaction rates.

Spontaneous and direct transformation of N,O-diaryl carbamates into N,N′-diarylureas

We have discovered a spontaneous reaction of N,O-diaryl carbamates to afford symmetrical N,N′-diarylureas. Optimization of the conditions indicated that N,N-dimethylformamide (DMF) was the best solvent and triethylamine (Et3N) was the best additive for this transformation. The reaction requires the presence of aryl groups on the nitrogen and oxygen atoms of carbamates. Substrates bearing an electron-donating methoxy group on either of the aryl groups reacted slowly under these conditions.

An efficient synthesis of nitrile, tetrazole and urea from carbonyl compounds

An efficient conversion of carbonyl compounds (aldehydes and ketones) to nitrile, tetrazole, and urea was developed with the use of a POCl3 and sodium azide mixture using a convergent and microwave method. This is the first report on the direct conversion of ketone to urea. The synthesized compounds were characterized by 1H NMR, 13C NMR, mass and IR spectroscopies and were found to be in agreement with reported compounds.

METHOD OF PRODUCING AROMATIC UREA COMPOUND

PROBLEM TO BE SOLVED: To provide a method realizing high-yield production of an aromatic urea compound at relatively low temperature without using highly toxic compounds as ingredients and without corrosive or toxic gas by-products.SOLUTION: A method of producing an aromatic urea compound comprises reacting an aromatic compound having one amino group with a compound represented by the formula (1) (X, X=H or Cl) in the presence of a basic salt, an organic base or their mixture as a catalyst, thereby obtaining an aromatic compound having a urea bond.