5-Amino-1,3-dihydro-2H-benzimidazol-2-one

Base Information

• Chemical Name: 5-Amino-1,3-dihydro-2H-benzimidazol-2-one
• CAS No.: 95-23-8
• Deprecated CAS: 40352-51-0
• Molecular Formula: C7H7N3O
• Molecular Weight: 149.152
• Hs Code.: 2933990090
• European Community (EC) Number: 202-401-8
• UNII: 3V3FDT3X0M
• DSSTox Substance ID: DTXSID5059119
• Nikkaji Number: J26.613B
• Wikidata: Q27895420
• Mol file: 95-23-8.mol

Synonyms:95-23-8;5-Amino-1,3-dihydro-2H-benzimidazol-2-one;5-amino-1,3-dihydrobenzimidazol-2-one;2H-Benzimidazol-2-one, 5-amino-1,3-dihydro-;5-amino-1H-benzo[d]imidazol-2(3H)-one;5-Amino-1,3-dihydro-benzoimidazol-2-one;5-Amino-2-benzimidazolinone;5-amino-2-hydroxybenzimidazole;MFCD00053555;5-amino-2,3-dihydro-1H-1,3-benzodiazol-2-one;3V3FDT3X0M;5-Amino-1,3-dihydrobenzoimidazol-2-one;EINECS 202-401-8;5-Aminobenzimidazolinone;40352-51-0;EC 202-401-8;5-AMINO-1H-BENZO(D)IMIDAZOL-2(3H)-ONE;5-Amino-1,3-dihydro-2H-benzimidazol-2-one, AldrichCPR;5(6)-Aminobenzoimidazolone;UNII-3V3FDT3X0M;Oprea1_319016;Oprea1_759802;SCHEMBL92048;SCHEMBL1695075;5-Amino-1H-benzimidazol-2-ol;DTXSID5059119;5-amino-2-hydroxy-1h-benzimidazole;BBL028058;CL3530;STK013932;2-HYDROXY-5-AMINOBENZIMIDAZOLE;AKOS000103534;AKOS008966788;2-BENZIMIDAZOLINONE, 5-AMINO-;CS-W019563;5-AMINO-2(3H)-BENZIMIDAZOLONE;5-amino-1,3-dihydro-benzimidazol-2-one;5-amino-2-oxo-2,3-dihydro-benzimidazol;5-amino-1,3-dihydro-benzimidazole-2-one;AC-10272;AS-11577;SY007179;5-amino-1H-benzo[d]imidazole-2(3H)-one;5-AMINO-1H-BENZO[D]IMIDAZOL-2-OL;5-AMINO-1H-BENZIMIDAZOL-2(3H)-ONE;AM20060881;BB 0217068;EU-0078496;FT-0602487;FT-0659613;EN300-02381;A825066;2-OXO-2,3-DIHYDRO-1H-BENZIMIDAZOL-5-AMINE;W-100170;2H-1,3-Benzimidazol-2-one, 5-amino-1,3-dihydro-;5-AMINO-2-OXO-2,3-DIHYDRO-1H-BENZIMIDAZOLE;Q27895420;Z56793257;F0074-0058

Chemical Property of 5-Amino-1,3-dihydro-2H-benzimidazol-2-one

Chemical Property:

• Appearance/Colour: Solid.
• Vapor Pressure: 0.308mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.657
• Boiling Point: 201.4 °C at 760 mmHg
• PKA: 11.80±0.30(Predicted)
• Flash Point: 75.6 °C
• PSA: 74.67000
• Density: 1.363 g/cm³
• LogP: 1.01960
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.058911855
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-2-hydroxybenzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1N)NC(=O)N2
• Uses: 5-Amino-2-hydroxybenzimidazole is an important reagent in the discovery of potent and selective non-nucleotide small molecule inhibitors of CD73

Technology Process of 5-Amino-1,3-dihydro-2H-benzimidazol-2-one

There total 6 articles about 5-Amino-1,3-dihydro-2H-benzimidazol-2-one 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: 95.0%

5-nitro-2,3-dihydro-1H-benzimidazol-2-one (93-84-5) → 5-amino-1,3-dihydro-benzoimidazol-2-one (95-23-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 24h; under 155.149 Torr; Sealed tube;

DOI:10.1002/cmdc.201900481

Reference yield: 94.6%

C13H10N4O → 5-amino-1,3-dihydro-benzoimidazol-2-one (95-23-8)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 85 ℃; for 4h; under 15001.5 Torr; Solvent; Pressure; Autoclave;

Reference yield: 73.0%

→ 5-amino-1,3-dihydro-benzoimidazol-2-one (95-23-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h;

upstream raw materials:

5-nitro-2,3-dihydro-1H-benzimidazol-2-one

hydrogenchloride

ethyl N-(2,4-dinitrophenylcarbamate)

4-Nitrophenylene-1,2-diamine

Downstream raw materials:

2-(2-Oxo-2,3-dihydro-1H-benzoimidazol-5-ylamino)-benzoic acid

7-(2-hydroxybenzoyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one

C₂₃H₂₈N₄O₅S

2-chloro-N-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-acetamide

Refernces

• 1、 -. "Synthetic method for preparing 5-aminobenzimidazolone". Paragraph 0023; 0031; 0037-0042; 0048-0052. . Retrieved 2021/07/17.
• 2、 -. "Novel hydrazone derivatives comprising aryl or heteroaryl group substituted at terminal amine and use thereof". Paragraph 1702; 1708; 1709; 1754; 1756-1758. . Retrieved 2020/08/28.