1H-Benzimidazole-2-carboxaldehyde

Base Information

• Chemical Name: 1H-Benzimidazole-2-carboxaldehyde
• CAS No.: 3314-30-5
• Molecular Formula: C8H6N2O
• Molecular Weight: 146.148
• Hs Code.: 2933990090
• European Community (EC) Number: 222-004-3
• NSC Number: 405912,26309
• UNII: W72HN35PDJ
• DSSTox Substance ID: DTXSID40186791
• Nikkaji Number: J110.017C
• Wikidata: Q27116911
• Metabolomics Workbench ID: 55446
• Mol file: 3314-30-5.mol

Synonyms:3314-30-5;1H-Benzimidazole-2-carboxaldehyde;1h-benzo[d]imidazole-2-carbaldehyde;1H-Benzimidazole-2-carbaldehyde;1H-Benzoimidazole-2-carboxaldehyde;Benzimidazole-2-carbaldehyde;2-Formylbenzimidazole;1H-Benzoimidazole-2-carbaldehyde;2-Benzimidazolecarboxaldehyde;1h-1,3-benzodiazole-2-carbaldehyde;MFCD00228045;W72HN35PDJ;EINECS 222-004-3;NSC-26309;NSC-405912;1H-Benzo(d)imidazole-2-carbaldehyde;azaindole aldehyde;NSC26309;UNII-W72HN35PDJ;SCHEMBL376644;SCHEMBL3279092;SCHEMBL9541649;CHEBI:36636;DTXSID40186791;1H-Benzimidazole-2-carbaldehyde #;2-BENZIMIDAZOLYLFORMALDEHYDE;BCP26408;BBL028429;NSC 26309;NSC405912;STK402277;1H-1,3-benzimidazole-2-carbaldehyde;AKOS001732208;AB04996;BS-3819;CS-W004873;NSC 405912;AM807094;BP-11203;SY025423;A5916;BB 0237076;FT-0601180;EN300-66936;J-504653;Q27116911;Z57114985;F0852-0139;1H-Benzo[d]imidazole-2-carbaldehyde

Chemical Property of 1H-Benzimidazole-2-carboxaldehyde

Chemical Property:

• Vapor Pressure: 2.02E-05mmHg at 25°C
• Melting Point: 224 °C
• Refractive Index: 1.747
• Boiling Point: 361.771 °C at 760 mmHg
• PKA: 10.61±0.10(Predicted)
• Flash Point: 176.353 °C
• PSA: 45.75000
• Density: 1.369 g/cm³
• LogP: 1.37540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.048012819
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

97% ^*data from raw suppliers

1H-Benzo[d]imidazole-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)NC(=N2)C=O
• General Description: 1H-Benzimidazole-2-carboxaldehyde (also known as 2-benzimidazolecarboxaldehyde or 2-formylbenzimidazole) is a versatile heterocyclic aldehyde that serves as a key intermediate in the synthesis of biologically active heterocycles, such as pyrrolo[1,2-a]quinoxalines. It participates in copper-catalyzed annulation reactions with o-aminoiodoarenes, demonstrating its utility in constructing complex nitrogen-containing scaffolds relevant to pharmaceutical applications. The compound's reactivity under optimized catalytic conditions highlights its importance in medicinal chemistry and drug discovery.

Technology Process of 1H-Benzimidazole-2-carboxaldehyde

There total 9 articles about 1H-Benzimidazole-2-carboxaldehyde 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: 86.0%

2-(Hydroxymethyl)benzimidazole (4856-97-7) → 1H-benzoimidazole-2-carboxaldehyde (3314-30-5)

Guidance literature:

With KMnO₄/alumina; at 20 ℃; for 0.133333h;

Reference yield: 85.3%

2-(dichloromethyl)-1H-benzimidazole (5466-57-9) → 1H-benzoimidazole-2-carboxaldehyde (3314-30-5)

Guidance literature:

With sulfuric acid; In water; at 80 ℃; for 1h;

Reference yield: 81.0%

1,2-diamino-benzene (95-54-5) + Glyoxilic acid (298-12-4) → 1H-benzoimidazole-2-carboxaldehyde (3314-30-5)

Guidance literature:

With hydroxyapatite; In water; at 52 ℃; for 6h; Temperature;

upstream raw materials:

2-Methyl-1H-benzimidazole

2-(Hydroxymethyl)benzimidazole

2-(dichloromethyl)-1H-benzimidazole

oxalic acid

Downstream raw materials:

2-benzimidazolecarboxylic acid

benzimidazole-2-carboxaldehyde dimethyl acetal

α-anilino-3-benzimidazolemethanol

diethyl phosphonate

Refernces

Copper-catalyzed annulation of 2-formylazoles with o-aminoiodoarenes

10.1021/jo9025644

The research focuses on the development of a copper-catalyzed annulation reaction between 2-formylazoles and o-aminoiodoarenes, leading to the synthesis of substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. This method provides a one-step route to these biologically active molecules, which are present in a growing number of pharmaceutical compounds. The reaction conditions were optimized using 2-iodoaniline and 2-formylpyrrole as starting materials, with the best results obtained using 1 equivalent of 2-formylpyrrole, 1.5 equivalents of 2-iodoaniline, 2 equivalents of K3PO4, 10 mol % CuI, 20 mol % sparteine, and NMP as the solvent at 130°C for 24 hours. The reaction was found to be effective for a variety of substituted aminoiodoarenes and formylazoles, including 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole. The synthesized products were analyzed using techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS) to confirm their structures and purities.