Hexahydro-2-benzimidazolinone

Base Information

• Chemical Name: Hexahydro-2-benzimidazolinone
• CAS No.: 1123-97-3
• Molecular Formula: C₇H₁₂N₂O
• Molecular Weight: 140.185
• European Community (EC) Number: 683-083-1
• DSSTox Substance ID: DTXSID10920725
• Nikkaji Number: J41.294E
• Mol file: 1123-97-3.mol

Synonyms:Hexahydro-2-benzimidazolinone;1123-97-3;octahydro-2h-benzimidazol-2-one;2-Benzimidazolinone, hexahydro-;2H-Benzimidazol-2-one, octahydro-;1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one;hexahydro-1H-benzo[d]imidazol-2(3H)-one;SCHEMBL2881411;DTXSID10920725;4,5-tetramethylene-2-imidazolinone;AKOS006351713;LS-33254;3a,4,5,6,7,7a-Hexahydro-1H-benzimidazol-2-ol

Chemical Property of Hexahydro-2-benzimidazolinone

Chemical Property:

• Vapor Pressure: 1.59E-05mmHg at 25°C
• Melting Point: 149-152 °C(lit.)
• Refractive Index: 1.486
• Boiling Point: 365.2 °C at 760 mmHg
• Flash Point: 181.2 °C
• PSA: 41.13000
• Density: 1.084 g/cm³
• LogP: 1.26800
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 140.094963011
• Heavy Atom Count: 10
• Complexity: 142

Purity/Quality:

98%,99%, ^*data from raw suppliers

cis-Octahydro-2H-benzimidazol-2-one 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC2C(C1)NC(=O)N2
• Uses: cis-Octahydro-2H-benzimidazol-2-one may be used in the preparation of hemicyclohexyl-cucurbit[n]uril (hmcyCucn).

Technology Process of Hexahydro-2-benzimidazolinone

There total 10 articles about Hexahydro-2-benzimidazolinone 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: 95.9%

carbon dioxide (124-38-9,18923-20-1) + rac-diaminocyclohexane (694-83-7) → 4,5,6,7-Tetrahydrobenzimidazolidin-2-one (1123-97-3,7237-97-0,139121-98-5)

Guidance literature:

at 180 ℃; for 24h; under 75007.5 Torr; Autoclave;

DOI:10.1039/c0gc00059k

Reference yield: 95.0%

carbon monoxide (201230-82-2) + trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7) → (rac)-trans-4,5-tetramethyleneimidazolidin-2-one (1123-97-3,7237-97-0,139121-98-5)

Guidance literature:

With C₆₂H₅₂AgAu₄N₂O₄P₄⁽³⁺⁾*3F₆Sb^(1-); In tetrahydrofuran; at 60 ℃; for 24h; under 3750.38 Torr; Inert atmosphere;

DOI:10.1002/anie.201603200

Reference yield: 76.0%

rac-diaminocyclohexane (694-83-7) + urea (57-13-6) → 4,5,6,7-Tetrahydrobenzimidazolidin-2-one (1123-97-3,7237-97-0,139121-98-5)

Guidance literature:

With copper diacetate; In tert-Amyl alcohol; at 140 ℃; for 8h; Inert atmosphere;

DOI:10.1002/anie.201108599

upstream raw materials:

phosgene

rac-diaminocyclohexane

2-aminocyclohexanecarboxamide

2-amino-cyclohexanecarboxylic acid ethyl ester

Refernces

• 1、 Kothandaraman, Jotheeswari,Kar, Sayan,Sen, Raktim,Goeppert, Alain,Olah, George A.,Prakash, G. K. Surya. "Efficient Reversible Hydrogen Carrier System Based on Amine Reforming of Methanol". supporting information. p. 2549 - 2552. Retrieved 2017/03/01.
• 2、 Smirnova, Ekaterina S.,Mu?oz Molina, José M.,Johnson, Alice,Bandeira, Nuno A. G.,Bo, Carles,Echavarren, Antonio M.. "Polynuclear Gold [AuI]4, [AuI]8, and Bimetallic [AuI4AgI] Complexes: C?H Functionalization of Carbonyl Compounds and Homogeneous Carbonylation of Amines". supporting information. p. 7487 - 7491. Retrieved 2016/07/06.