methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate

Base Information

• Chemical Name: methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate
• CAS No.: 292070-01-0
• Molecular Formula: C9H9N3O2
• Molecular Weight: 191.189
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50590805
• Wikidata: Q82484440
• Mol file: 292070-01-0.mol

Synonyms:292070-01-0;methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate;5-Amino-1H-benzoimidazole-2-carboxylic acid methyl ester;methyl 6-amino-1H-benzimidazole-2-carboxylate;1H-Benzimidazole-2-carboxylic acid, 6-amino-, methyl ester;methyl 5-amino-1H-1,3-benzodiazole-2-carboxylate;MFCD07368329;Methyl 5-Aminobenzimidazole-2-carboxylate;SCHEMBL4314310;6-amino-1H-benzimidazole-2-carboxylic acid methyl ester;DTXSID50590805;KPLHXWFXDADDMP-UHFFFAOYSA-N;5-AMINO-1H-BENZOIMIDAZOLE-2-CARBOXYLICACIDMETHYLESTER;AKOS006286773;AKOS015914057;AC-29378;AS-78301;SY036628;DB-068082;CS-0160735;EN300-152561;F31231;methyl 6-azanyl-1H-benzimidazole-2-carboxylate;A819809;6-Amino-1H-benzoimidazole-2-carboxylic acid methyl ester

Chemical Property of methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate

Chemical Property:

• Boiling Point: 430.8 °C at 760 mmHg
• PKA: 9.94±0.10(Predicted)
• Flash Point: 214.3 °C
• PSA: 81.00000
• Density: 1.413 g/cm³
• LogP: 1.51290
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 191.069476538
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl5-amino-1H-benzo[d]imidazole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC2=C(N1)C=C(C=C2)N

Technology Process of methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate

There total 5 articles about methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate 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: 78.0%

methyl 5-nitro-1H-benzo[d]imidazole-2-carboxylate (93521-65-4) → methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate (292070-01-0)

Guidance literature:

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

Reference yield: 60.0%

BICA methyl ester (5805-53-8) → methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate (292070-01-0)

Guidance literature:

BICA methyl ester; With sulfuric acid; nitric acid; at 0 ℃; for 1.5h;

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 18h; under 760.051 Torr; Further stages.;

DOI:10.1021/ja994192d

Reference yield:

2-(Hydroxymethyl)benzimidazole (4856-97-7) → methyl 5-amino-1H-benzo[d]imidazole-2-carboxylate (292070-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 54 percent / MnO₂; NaCN / 18 h / 25 °C

2.1: H₂SO₄; HNO₃ / 1.5 h / 0 °C

2.2: 60 percent / H₂ / Pd/C / ethyl acetate / 18 h / 25 °C / 760.05 Torr

With manganese(IV) oxide; sulfuric acid; sodium cyanide; nitric acid;

DOI:10.1021/ja994192d

upstream raw materials:

BICA methyl ester

2-(Hydroxymethyl)benzimidazole

5-nitro-2-(trichloromethyl)-1H-benzo[d]imidazole

methyl 5-nitro-1H-benzo[d]imidazole-2-carboxylate

Refernces

• 1、 Boger, Dale L.,Fink, Brian E.,Hedrick, Michael P.. "Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity". . p. 6382 - 6394. Retrieved 2007/10/03.