1,3-Diphenylurea

Base Information

• Chemical Name: 1,3-Diphenylurea
• CAS No.: 102-07-8
• Molecular Formula: C13H12N2O
• Molecular Weight: 212.251
• Hs Code.: 29242100
• European Community (EC) Number: 203-003-7
• NSC Number: 227401,8485
• UNII: 94YD8RMX5B
• DSSTox Substance ID: DTXSID2025183
• Nikkaji Number: J5.003B
• Wikipedia: 1,3-Diphenylurea
• Wikidata: Q27096716
• Pharos Ligand ID: D57HZ1NZCBAW
• Metabolomics Workbench ID: 45248
• ChEMBL ID: CHEMBL354676
• Mol file: 102-07-8.mol

Synonyms:1,3-Diphenylurea;102-07-8;N,N'-Diphenylurea;CARBANILIDE;Diphenylurea;Diphenylcarbamide;s-Diphenylurea;Urea, N,N'-diphenyl-;sym-Diphenylurea;Acardite;Acardite I;N-Phenyl-N'-phenylurea;1,3-Diphenylcarbamide;Karbanilid;N,N'-Difenylmocovina;USAF EK-534;Urea, 1,3-diphenyl-;Karbanilid [Czech];1,3-diphenyl-urea;AD 30;NSC 227401;N,N'-Difenylmocovina [Czech];CCRIS 4634;Diphenylurea, 1,3-;HSDB 2757;Urea-based compound, 7;EINECS 203-003-7;UNII-94YD8RMX5B;BRN 0782650;94YD8RMX5B;AI3-52320;DTXSID2025183;CHEBI:41320;N,N'-DIPHENYLUREA D10;Urea,3-diphenyl-;Urea,N'-diphenyl-;NSC-227401;WLN: RMVMR;4-12-00-00741 (Beilstein Handbook Reference);N'N'-Diphenyl urea;SR-01000398115;bis-phenyl-urea;Zeonet U;2zjf;n,n'-diphenyl-urea;MFCD00003017;N, N'-diphenylurea;N,N'-diphenyl urea;1, 3-Diphenylurea;1,3-diphenylurinstof;Kinome_598;Kinome_627;N,N'-bis-Phenylurea;Spectrum_000422;SpecPlus_000406;CARBANILIDE [MI];Spectrum2_001838;Spectrum3_001328;Spectrum4_001561;Spectrum5_000182;1 pound not3-diphynylurea;CARBANILIDE [HSDB];D0X7IM;1,3-Diphenylurea, 98%;Oprea1_527136;BSPBio_003055;CBDivE_002165;KBioGR_002082;KBioSS_000902;SPECTRUM211126;MLS002207104;DivK1c_006502;SCHEMBL133103;SPBio_001915;CHEMBL354676;DTXCID305183;SCHEMBL21313806;BDBM25725;KBio1_001446;KBio2_000902;KBio2_003470;KBio2_006038;KBio3_002275;NSC8485;3e85;NSC-8485;RKL10128;Tox21_200068;CCG-38465;GEO-04213;ICCB1_000093;LS-354;NSC227401;NSC794585;STK328350;AKOS000312994;CS-W015002;DB07496;FS-4202;NSC-794585;SDCCGMLS-0066513.P001;NCGC00091344-01;NCGC00091344-02;NCGC00091344-03;NCGC00091344-04;NCGC00091344-05;NCGC00257622-01;AC-12855;CAS-102-07-8;SMR000112141;Carbanalide 100 microg/mL in Acetonitrile;EU-0067898;FT-0606720;F20340;1,3-Diphenylurea, Vetec(TM) reagent grade, 98%;A896907;AQ-917/40171059;SR-01000398115-1;SR-01000398115-2;W-108886;BRD-K13027645-001-02-0;Q27096716

Chemical Property of 1,3-Diphenylurea

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 2.5E-05mmHg at 25°C
• Melting Point: 239-241 °C(lit.)
• Refractive Index: 1.651
• Boiling Point: 262 °C at 760 mmHg
• PKA: 14.15±0.70(Predicted)
• Flash Point: 91.147 °C
• PSA: 41.13000
• Density: 1.25 g/cm³
• LogP: 3.47660
• Storage Temp.: Store at RT.
• Solubility.: pyridine: soluble50mg/mL, clear to very slightly hazy, colorless
• Water Solubility.: 150.3mg/L(temperature not stated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 212.094963011
• Heavy Atom Count: 16
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

1,3-Diphenylurea ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:Harmful if swallowed.
• Hazard Codes: R22:Harmful if swallowed.
• Statements: R22:Harmful if swallowed.
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Urea Compounds
• Canonical SMILES: C1=CC=C(C=C1)NC(=O)NC2=CC=CC=C2
• Chemical Composition and Structure: 1,3-Diphenylurea (DPU) is a member of the phenylurea class which consists of a urea molecule in which one hydrogen of each amino group is substituted by a phenyl group.
• Uses: 1,3-Diphenylurea serves as a synthetic intermediate for phosgene-free synthesis of methyl N-phenylcarbamate and phenyl isocyanate, important in chemical technology.^[1]; ; Designed and synthesized as dual-target-directed ligands for Alzheimer's disease, combining BACE 1 inhibitory activity and metal chelation properties.^[2]; ; Exhibits phase transition behavior under high pressure, with potential applications in materials science.^[3]
• Production Methods: Found in coconut milk (Cocos nucifera) and synthesized through chemical routes involving catalyzed reductive carbonylation of nitrobenzene in laboratory settings.
• References: [1] Phosgene-free synthesis of 1,3-diphenylurea via catalyzed reductive carbonylation of nitrobenzene; DOI 10.1351/PAC-CON-11-07-15; [2] Dual-target-directed 1,3-diphenylurea derivatives: BACE 1 inhibitor and metal chelator against Alzheimer’s disease; DOI 10.1016/j.bmc.2010.06.042; [3] High-pressure-induced phase transition in 1,3-diphenylurea: The approaching of N–H?O hydrogen-bonded chains; DOI 10.1002/jrs.5706

Technology Process of 1,3-Diphenylurea

There total 746 articles about 1,3-Diphenylurea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

4-Hydroxy-5,5-dimethyl-3,4-diphenyl-oxazolidin-2-one → 2-methyl-1-phenylprop-2-en-1-one (769-60-8) + 3-hydroxy-3-phenyl-butan-2-one (3155-01-9) + phenyl isocyanate (103-71-9) + bis(diphenyl)urea (102-07-8)

Guidance literature:

In benzene; at 450 ℃; Further byproducts given;

Reference yield: 64.0%

phenyl carbamate (64-10-8) + para-nitrophenyl bromide (586-78-7) → 4-ntrophenyl(phenyl)amine (836-30-6) + N-(4-nitrophenyl)-N'-phenylurea (1932-32-7) + N,N-bis(p-nitrophenyl)amine (1821-27-8) + bis(diphenyl)urea (102-07-8)

Guidance literature:

With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00716-X

Reference yield: 57.0%

O-phenylcarbamoyl-4-nitrobenzohydroxamic acid → N-(4-nitrophenyl)-N'-phenylurea (1932-32-7) + 4-nitro-aniline (100-01-6,104810-17-5) + aniline (62-53-3) + bis(diphenyl)urea (102-07-8)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 90 ℃;

DOI:10.1039/c6ob01178k

upstream raw materials:

2-Benzoxazolinone

aniline

2,4-dimethyl-1,2,4-thiadiazolidine-3-thione-5-one

1,3-benzoxazine-2,4-dione

Downstream raw materials:

1-(N-phenylcarbamoyl)piperidine

(3-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinolin-4-yl)-phenyl-amine

Acetanilid

N,N-Diphenyl-acetamidine

Refernces

A combined experimental and computational investigation on the unusual molecular mechanism of the lossen rearrangement reaction activated by carcinogenic halogenated quinones

10.1021/jo5022713

The study investigates the unusual molecular mechanism of the Lossen rearrangement reaction activated by carcinogenic halogenated quinones. It explores how chlorinated benzoquinones (CnBQ) serve as new activating agents for benzohydroxamic acid (BHA), leading to the Lossen rearrangement. The chemicals involved include various chlorinated benzoquinones (such as TCBQ, 2,5-DCBQ, 2,6-DCBQ, 2-CBQ, and TrCBQ), benzohydroxamic acid (BHA), phenyl isocyanate (Ph-NCO), and N,N′-diphenylurea. The study finds that the stability of CnBQ-activated BHA intermediates depends on both the degree and position of Cl-substitution on CnBQs, which can be divided into two subgroups based on their stability. The rate of the CnBQ-activated rearrangement is determined by the relative energy of the anionic CnBQ?BHA intermediates, with the Cl or H ortho to the reaction site at CnBQ being crucial for the stability of these intermediates. A pKa?activation energy correlation is observed, linking the rate of rearrangement to the acidity of the conjugate acid of the anionic leaving group. The study combines experimental and computational methods to provide insights into this novel halogenated quinone-activated Lossen rearrangement, which has implications for understanding the detoxification of carcinogenic quinones and the potential biomedical applications of hydroxamic acids.

Discovery of a novel and potent series of dianilinopyrimidineurea and urea isostere inhibitors of VEGFR2 tyrosine kinase

10.1016/j.bmcl.2005.05.096

The research focuses on the discovery and development of a novel series of dianilinopyrimidineurea and urea isostere inhibitors targeting the VEGFR2 tyrosine kinase, which plays a crucial role in angiogenesis, a process implicated in various diseases and cancer growth. The purpose of this study was to develop compounds that could inhibit VEGFR2, potentially starving cancers of necessary blood flow by limiting vasculature to the growth site. The researchers synthesized a series of dianilinopyrimidine ureas and urea isosteres, which were found to be low nanomolar inhibitors of the VEGFR2 enzyme and exhibited anti-proliferative activity on human umbilical vein endothelial cells (HUVECs). Key chemicals used in the synthesis process included 2,4-dichloropyrimidine, methyl iodide, cesium carbonate, isopropanol, hydrochloric acid, and various substituted anilines, among others. The study concluded that the urea class of compounds demonstrated the best enzyme and cell potency, with diphenylureas showing particular promise. The researchers proposed a likely binding mode for a representative compound from their urea series based on homology modeling and X-ray crystal analysis, providing a foundation for further development of VEGFR2 kinase inhibitors.