64-10-8

Basic information

• Product Name: PHENYLUREA
• Synonyms: N-PHENYLUREA;PHENYLCARBAMIDE;PHENYLUREA;1-Phenylurea;Monophenylurea;phenyl-ure;phenylureapesticide,liquid,flammable,poisonous;phenylureapesticide,liquid,poisonous
• CAS NO: 64-10-8
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• EINECS: 200-576-5
• Product Categories: Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Organic Building Blocks;P;Ureas
• Mol File: 64-10-8.mol

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 238 °C
• Flash Point: 238°C
• Appearance: White to light yellow/Powder, Crystals and/or Chunks
• Density: 1,302 g/cm3
• Vapor Density: >1 (vs air)
• Refractive Index: 1.5769 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 10 mg/mL, clear
• PKA: 13.37±0.50(Predicted)
• Water Solubility: Soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,7319
• BRN: 1934615
• CAS DataBase Reference: PHENYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLUREA(64-10-8)
• EPA Substance Registry System: PHENYLUREA(64-10-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36/37-24/25
• WGK Germany: 3
• RTECS: YU0650000
• TSCA: Yes
• Hazardous Substances Data: 64-10-8(Hazardous Substances Data)

Usage

Preparation

Phenylurea is synthesized by the reaction of aniline and urea. Put urea, hydrochloric acid and aniline into the reaction pot, heat and stir, reflux at 100-104°C for 1 hour, add water and stir, cool, filter, wash the filter cake with water, and dry to obtain the finished product of phenylurea.

Reactivity Profile

Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Contains any of several related compounds (Diuron, Fenuron, Linuron, Neburon, Siduron, Monuron) formally derived from urea.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

Purification Methods

Crystallise the urea from boiling water (10mL/g) or amyl alcohol (m 149o). Dry it in a steam oven at 100o. The 1:1 resorcinol complex has m 115o (from EtOAc/*C6H6). [Beilstein 12 H 346, 12 II 204, 12 III 760, 12 IV 734.]

InChI:InChI=1/C7H8N2O/c8-7(10)9-6-4-2-1-3-5-6/h1-5H,(H3,8,9,10)

Upstream product

• 861323-42-4 5-amino-3-methylimidazolidine-2,4-dione 
• 103-71-9 phenyl isocyanate 
• 10582-78-2 5-methylene-3-phenylimidazolidine-2,4-dione 
• 959-32-0 N-(benzoyloxy)benzamide 
• 2221-17-2 5-benzylidene-3-phenylhydantoin 
• 6784-22-1 phenylcarbamoyl cyanide 
• 4910-32-1 1,3-diphenylcarbamothioate 
• 4930-03-4 phenyl N-phenylcarbamate 
• 13911-40-5 N-phenylbiuret 
• 113546-44-4 N-chloro-N'-phenyl-urea 
• 857796-10-2 5-(α-acetoxy-benzyl)-3-phenyl-imidazolidine-2,4-dione 
• 67-56-1 methanol 
• 6268-32-2 N-phenyl-N-nitrosourea 
• 62-53-3 aniline 

Downstream Products

• 57469-23-5 N-cyano-N-phenylbenzenesulfonamide 
• 6331-74-4 N-phenyl-N'-xanthen-9-yl-urea 
• 859327-23-4 N-(2-bromo-propionyl)-N'-phenyl-urea 
• 31579-25-6 N-(chloro-phenyl-acetyl)-N'-phenyl-urea 
• 83-25-0 N-phenylmaleimide 
• 40899-11-4 N',N'''-diphenyl-N,N''-ethylidene-di-urea 
• 28584-90-9 N,N'-bis phenyl imidodicarbonic diamide 
• 19726-93-3 N-benzenesulfenyl-N'-phenyl-urea 
• 19383-55-2 N-(phenylcarbamoyl)furan-2-carboxamide 
• 19110-07-7 5-isopropyl-1-phenylbarbituric acid 
• 520-03-6 N-phenylphthalimide 
• 4727-29-1 phthalanilic acid 
• 56720-81-1 1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid anilide 
• 18872-98-5 1,1'-methylene-bis(3-phenylurea) 

Relevant articles and documents

Indium(III)-Catalyzed Synthesis of Primary Carbamates and N-Substituted Ureas

An indium triflate-catalyzed synthesis of primary carbamates from alcohols and urea as an ecofriendly carbonyl source has been developed. Various linear, branched, and cyclic alcohols were converted into the corresponding carbamates in good to excellent yields. This method also provided access to N-substituted ureas by carbamoylation of amines. All the products were obtained by simple filtration or crystallization, without the need for chromatographic purification. Mechanistic investigations suggest that the carbamoylation reaction proceeds through activation of urea by O-coordination with indium, followed by nucleophilic attack by the alcohol or amine on the carbonyl center of urea. The inexpensive and easily available starting materials and catalyst, the short reaction times, and the ease of product isolation highlight the inherent practicality of the developed method.

Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study

A series of novel pyrazole-phenyl semicarbazone derivatives were designed, synthesized, and screened for in vitro α-glucosidase inhibitory activity. Given the importance of hydrogen bonding in promoting the α-glucosidase inhibitory activity, pharmacophore modification was established. The docking results rationalized the idea of the design. All newly synthesized compounds exhibited excellent in vitro yeast α-glucosidase inhibition (IC50 values in the range of 65.1–695.0 μM) even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, compounds 8o displayed the most potent α-glucosidase inhibitory activity (IC50 = 65.1 ± 0.3 μM). Kinetic study of compound 8o revealed that it inhibited α-glucosidase in a competitive mode (Ki = 87.0 μM). Limited SAR suggested that electronic properties of substitutions have little effect on inhibitory potential of compounds. Cytotoxic studies demonstrated that the active compounds (8o, 8k, 8p, 8l, 8i, and 8a) compounds are also non-cytotoxic. The binding modes of the most potent compounds 8o, 8k, 8p, 8l and 8i was studied through in silico docking studies. Molecular dynamic simulations have been performed in order to explain the dynamic behavior and structural changes of the systems by the calculation of the root mean square deviation (RMSD) and root mean square fluctuation (RMSF).

Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides

The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Enzyme-Inspired Lysine-Modified Carbon Quantum Dots Performing Carbonylation Using Urea and a Cascade Reaction for Synthesizing 2-Benzoxazolinone

Catalysts as the dynamo of chemical reactions along with solvents play paramount roles in organic transformations in long-lasting modes. Thus, developing effective and biobased catalysts in nontoxic solvents is highly in demand. In this report, carbon quantum dots (CQDs) functionalized with-lysine (Lys-CQDs) were generated from entirely nature-derived materials; they were demonstrated to be a promising catalyst for C-N bond formation in choline chloride urea (ChCl/U), a natural deep eutectic solvent (NADES). Among a number of synthesized CQDs, Lys-CQD turned out to be a powerful catalyst in the model reaction with aniline to afford phenyl urea. This type of transformation is important because aniline as a nucleophile has low activity, and urea is a very weak electrophile but an abundant natural source of the carbonyl moiety at the same time. The optimized reaction was performed under a highly desirable condition without using tedious and toxic workup processes at a low temperature (37 °C for aliphatic amines and 60 °C for aniline derivatives), as well as by embracing the broad scope of products in good to high yields even with weak nucleophiles such as aniline. A proposed acid-activated mechanism was suggested for the model reaction that was further confirmed by detecting ammonia as the leaving group. To show further multifunctionality of the catalyst, a cascade catalysis approach was developed for synthesizing 2-benzoxazolinone, which was furnished in a two-step transformation, starting from 2-aminophenol. Using X-ray crystallography, the structure of the final product in the cascade reaction was also determined. The catalyst was characterized using various analytical techniques including SEM, TEM, AFM, XRD, IR spectroscopy, UV-vis spectroscopy, DLS, and fluorescence spectroscopy. Measuring the acid/base sites by back titration, the catalyst was shown to be highly functionalized by the lysine functional group. The size of the catalyst was determined to be in the range of 1-8 nm, having a well-dispersed surface. In all, Lys-modified CQD, as a metal-free catalyst, was synthesized, characterized, and optimized for carbonylation, as well as a cascade reaction, under mild conditions. The whole process including catalyst synthesis and organic transformations is economically competitive and fulfills all requirements toward viability.

Electrophotocatalytic C?H Heterofunctionalization of Arenes

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.

A Cu-Promoted C-N Coupling of Boron Esters and Diaziridinone: An Approach to Aryl Ureas

A novel Cu-promoted C-N coupling between boron esters and di-tert-butyldiaziridinone is described. A wide variety of aryl ureas can be readily obtained under mild conditions with up to a 92% yield.

Synthesis of Biuret Derivatives as Potential HIV-1 Protease Inhibitors Using (LDHs-g-HMDI-Citric Acid), as a Green Recyclable Catalyst

In this study, a novel catalyst based on layered double hydroxides (LDHs) attached by hexamethylene-1,6-diisocyanate (HMDI) and citric acid (LDHs-g-HMDI-Citric acid) is reported and used to increase the yield of biurets synthesis. Biuret derivatives 5a–n were prepared by reaction of several phenyl allophanates (3a–d), which prepared from the reaction of phenyl chloroformate and urea derivatives (2a–d), with variously substituted amines (4a–g) in the presence of LDHs-g-HMDI-Citric acid as a reusable heterogeneous catalyst at reflux condition for 60–180 min. These biurets (5a–n) were evaluated for human immunodeficiency virus type-1 (HIV-1) protease inhibitory activity by HIV-1 p24 antigen ELISA kit and six of them (5n, 5i, 5j, 5 m, 5f, and 5a) showed moderate activity on HIV-1 virus with IC50 values ranging from 55 to 100 μM compared with the azidothymidine as the reference drug (IC50 = 0.11 μM). Results of the in vitro test and docking study were in good correlation.

Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas

A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.