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:

1,5-dimethyl-3-oxo-N,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

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

Acetanilid

phenyl isocyanate

Refernces

• 1、 Boyer,Frints. "-". . p. 2449. Retrieved 1970.
• 2、 Dean,C.S. et al.. "-". . p. 3393 - 3397. Retrieved 1970.
• 3、 Yuan, Hao-Yu,Zhang, Qiao,Fukaya, Norihisa,Lin,Fujitani, Tadahiro,Choi, Jun-Chul. "Phosgene-free synthesis of carbamates using co2 and titanium alkoxides". . p. 1481 - 1486. Retrieved 2018.
• 4、 Mancuso, Raffaella,Raut, Dnyaneshwar S.,Della Ca, Nicola,Fini, Francesco,Carfagna, Carla,Gabriele, Bartolo. "Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones". . p. 2204 - 2211. Retrieved 2015.
• 5、 Murahashi,Horiie. "-". . p. 78. Retrieved 1960.
• 6、 Nitta, Makoto,Kobayashi, Tomoshige. "Nonacarbonyldiiron or Pentacarbonyliron Induced Decomposition of Organic Azides and an Azirine. Novel Reduction and Carbonyl Insertion of the Complexed Nitrene Intermediate in Protic Solvents". . p. 1035 - 1039. Retrieved 1984.
• 7、 Fattori, Daniela,D'Andrea, Piero,Porcelloni, Marina. "Solid-phase synthesis of unsymmetrical ureas through the use of Kenner safety-catch linker". . p. 811 - 814. Retrieved 2003.
• 8、 Gavade, Sandip,Balaskar, Ravi,Mane, Madhav,Pabrekar, Pramod N.,Mane, Dhananjay. "Cu(acac)2-catalyzed N-arylations of phenylurea with aryl boronic acid". . p. 1704 - 1714. Retrieved 2012.
• 9、 Kotecki, Brian J.,Fernando, Dilinie P.,Haight, Anthony R.,Lukin, Kirill A.. "A general method for the synthesis of unsymmetrically substituted ureas via palladium-catalyzed amidation". . p. 947 - 950. Retrieved 2009.
• 10、 Zheng, Shuzhan,Li, Fuwei,Liu, Jianming,Xia, Chungu. "A novel and efficient (NHC)CuI (NHC = N-heterocyclic carbene) catalyst for the oxidative carbonylation of amino compounds". . p. 5883 - 5886. Retrieved 2007.