1,3-Dicyclohexylurea

Base Information

• Chemical Name: 1,3-Dicyclohexylurea
• CAS No.: 2387-23-7
• Deprecated CAS: 1071714-16-3
• Molecular Formula: C13H24 N2 O
• Molecular Weight: 224.346
• Hs Code.: 29242100
• European Community (EC) Number: 219-213-7
• NSC Number: 30023,17013
• UNII: ZV7823VVIM
• DSSTox Substance ID: DTXSID3062366
• Nikkaji Number: J80.467C
• Wikipedia: Dicyclohexylurea
• Wikidata: Q5274028
• Pharos Ligand ID: D57HZ1NZCBAW
• Metabolomics Workbench ID: 123512
• ChEMBL ID: CHEMBL1458
• Mol file: 2387-23-7.mol

Synonyms:1,3-dicyclohexylurea;DCU compound;N,N'-dicyclohexylurea

Chemical Property of 1,3-Dicyclohexylurea

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 232-233 °C(lit.)
• Refractive Index: 1.4832 (estimate)
• Boiling Point: 408.2°Cat760mmHg
• PKA: 13.89±0.20(Predicted)
• Flash Point: 157.9°C
• PSA: 41.13000
• Density: 1.02g/cm³
• LogP: 3.73280
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 224.188863393
• Heavy Atom Count: 16
• Complexity: 196

Purity/Quality:

99.5% ^*data from raw suppliers

N,N''-Dicyclohexylurea ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CCC(CC1)NC(=O)NC2CCCCC2
• Uses: N,N''-Dicyclohexylurea,is a substituted Urea (U822500) compound, which has shown to be a potent inhibitor of juvenile hormone epoxide hydrolase (JHEH) of the tobacco hornworm M. sexta. Lomustine USP Related Compound C.

Technology Process of 1,3-Dicyclohexylurea

There total 455 articles about 1,3-Dicyclohexylurea 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: 64.5%

Boc-Asp-OH (13726-67-5) + dimethyl L-aspartate hydrochloride (32213-95-9) + triethylamine (121-44-8) → triethylamine hydrochloride (554-68-7) + 1,3-Dicyclohexylurea (2387-23-7) + Boc-Asp-[Asp-(OMe)2]2 (167082-77-1)

Guidance literature:

Boc-Asp-OH; dimethyl L-aspartate hydrochloride; triethylamine; With dicyclohexyl-carbodiimide; In tetrahydrofuran; at -10 - 5 ℃;

With acetic acid; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield: 59.0%

[NiBr2(cyclohexylamine)4] + cyclohexylamine (108-91-8,157973-60-9) → N,N'-dicyclohexyloxamide (3299-64-7) + cyclohexylammonium bromide (26227-54-3) + 1,3-Dicyclohexylurea (2387-23-7) + tetracarbonyl nickel (13463-39-3,71564-36-8)

Guidance literature:

With carbon monoxide; In tetrahydrofuran; diethyl ether; addn. of RNH2 to suspn. of complex, CO (40 bar), warmed up to 45°C, 20h, hydrolysis with H2SO4, sepn. of organic phase, dried, crystn. of organic products from hexane/CHCl3 = 20/1;

DOI:10.1016/S0022-328X(00)99113-7

Reference yield: 55.0%

n-butyllithium (109-72-8,29786-93-4) + dicyclohexyl-carbodiimide (538-75-0) + para-chlorobenzoic acid (74-11-3) → 1-(4-chlorophenyl)pentan-1-one (25017-08-7) + 1,3-Dicyclohexylurea (2387-23-7)

Guidance literature:

dicyclohexyl-carbodiimide; para-chlorobenzoic acid; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.04.030

upstream raw materials:

ethanol

2-chloro-6-nitrobenzothiazole

1,3-dicyclohexylthiourea

S-butyl cyclohexylcarbamothioate

Downstream raw materials:

N-cyanoacetyl-1,3-dicyclohexylurea

2,4-bis(4-methoxyphenyl)-3-cyclohexyl-1,3,2,4-thiazadiphosphetane 2,4-disulfide

1,3-dicyclohexylthiourea

ethyl 2-(1,3-dicyclohexylhexahydro-2-oxo-1,3,5-triazin-5-yl)acetate

Refernces

• 1、 Rani, N. Latha,Chakravarthy,Mohana,Lokanath,Sridhar. "Synthesis, characterization and hirshfeld surface analysis of a 2-thiophene acetic acid derivative". . p. 223 - 231. Retrieved 2015.
• 2、 Butowska, Kamila,Kozak, Witold,Zdrowowicz, Magdalena,Makurat, Samanta,Rych?owski, Micha?,Ha?, Aleksandra,Herman-Antosiewicz, Anna,Piosik, Jacek,Rak, Janusz. "Cytotoxicity of doxorubicin conjugated with C60 fullerene. Structural and in vitro studies". . p. 2327 - 2338. Retrieved 2019.
• 3、 Misra, Arvind,Shahid, Mohammad,Dwivedi, Pratibha. "N-(3-Triethoxysilylpropyl)-4-(isothiocyanatomethyl)-cyclohexane-1-carboxamide (TPICC): A heterobifunctional reagent for immobilization of biomolecules on glass surface". . p. 5217 - 5221. Retrieved 2008.
• 4、 Formaggio, Fernando,Peggion, Cristina,Crisma, Marco,Toniolo, Claudio,Tchertanov, Luba,Guilhem, Jean,Mazaleyrat, Jean-Paul,Goubard, Yolaine,Gaucher, Anne,Wakselman, Michel. "A chirally stable, atropoisomeric, Cα-tetrasubstituted α-amino acid: Incorporation into model peptides and conformational preference". . p. 481 - 501. Retrieved 2001.
• 5、 Na, Kun,Lee, Kwang Hee,Lee, Don Haeng,Bae, You Han. "Biodegradable thermo-sensitive nanoparticles from poly(L-lactic acid)/poly(ethylene glycol) alternating multi-block copolymer for potential anti-cancer drug carrier". . p. 115 - 122. Retrieved 2006.
• 6、 Balcom, Bruce J.,Petersen, Nils O.. "Solvent Dependence of Carboxylic Acid Condensations with Dicyclohexylcarbodiimide". . p. 1922 - 1927. Retrieved 1989.
• 7、 Moriuchi, Toshiyuki,Sakuramoto, Takashi,Matsutani, Takanari,Kawai, Ryota,Donaka, Yosuke,Tobisu, Mamoru,Hirao, Toshikazu. "Oxovanadium(v)-catalyzed amination of carbon dioxide under ambient pressure for the synthesis of ureas". . p. 27121 - 27125. Retrieved 2021/08/24.
• 8、 Zhao, Yulei,Guo, Xuqiang,Si, Zhiyao,Hu, Yanan,Sun, Ying,Liu, Yunlin,Ji, Zhongyin,You, Jinmao. "Hydrosilane-Assisted Synthesis of Urea Derivatives from CO2and Amines". . p. 13347 - 13353. Retrieved 2020/11/02.