72721-02-9

Basic information

• Product Name: 5,6-Dimethoxybenzimidazole
• Synonyms: 5,6-DIMETHOXYBENZIMIDAZOLE;1H-Benzimidazole,5,6-dimethoxy-(9CI);5,6-dimethoxy-1H-benzo[d]imidazole;5,6-Dimethoxy-1H-benzimidazole;5,6-diMethoxy-1H-1,3-benzodiazole;1H-BenziMidazole, 5,6-diMethoxy-
• CAS NO: 72721-02-9
• Molecular Formula: C₉H₁₀N₂O₂
• Molecular Weight: 178.19
• EINECS: -0
• Product Categories: BENZIMIDAZOLE;Imidazol&Benzimidazole
• Mol File: 72721-02-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 183-189°C
• Boiling Point: 398.6 °C at 760 mmHg
• Flash Point: 144.6 °C
• Appearance: /
• Density: 1.245 g/cm³
• PKA: 13.46±0.30(Predicted)
• CAS DataBase Reference: 5,6-Dimethoxybenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dimethoxybenzimidazole(72721-02-9)
• EPA Substance Registry System: 5,6-Dimethoxybenzimidazole(72721-02-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 72721-02-9(Hazardous Substances Data)

Usage

General Description

5,6-Dimethoxybenzimidaole, also known as CAS no. 56205-66-6, is an organic compound characterized by its chemical formula C9H10N2O2. It takes the form of an off-white crystalline powder and is moderately soluble in water. It is typically used in the field of pharmaceuticals, serving as a vital intermediate in the synthesis of various drugs. Due to its specific chemical structure, it possesses biological activities that contribute to its effective performance in pharmaceutical applications. Its safe usage requires appropriate protections, as exposure may cause eye or skin irritation and have some harmful effects if absorbed into the body.

Upstream product

• 64-18-6 formic acid 
• 88580-71-6 1,2-diamino-4,5-dimethoxybenzene monohydrochloride 
• 131076-14-7 4,5-dimethoxy-1,2-phenylenediamine hydrochloride salt 
• 27841-33-4 4,5-dimethoxybenzene-1,2-diamine 
• 91-16-7 1,2-dimethoxybenzene 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 

Downstream Products

• 102169-73-3 5,6-Dihydroxybenzimidazole 
• 4701-07-9 5,6-dimethoxy-1-methylbenzimidazole 
• 5118-06-9 methyl 3-hydroxy-2-thiophenecarboxylate 

Relevant articles and documents

Efficient N-Heterocyclic Carbene/Ruthenium Catalytic Systems for the Alcohol Amidation with Amines: Involvement of Poly-Carbene Complexes?

The atom-economic direct amidation of alcohols with amines has been recently highlighted as an attractive and promising transformation. Among the versatile reported catalytic systems, in situ generated N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic systems have demonstrated their advantages such as easy operation and use of commercial Ru compounds. However, the existing catalyst loadings are relatively high, and additional insights for the in situ catalyst generation are still not well-documented. In this work, a variety of benzimidazole-based NHC precursors were initially synthesized. Through the screening of various NHC precursors and other reaction conditions, active in situ catalytic systems were discovered for the efficient amide synthesis. Notably, the catalyst loading is as low as 0.5 mol %. Furthermore, additional experiments were performed to validate the rationale for the superiority of the current catalytic systems over our previous system. It was observed that the ligand structure is one of the reasons for the higher activity. In addition, the higher ratio of the NHC precursor/[Ru] is another important factor for the improvement. Further HR-MS analysis identified the formation of two mono-NHC-Ru species as major species and two Ru species bearing multiple NHC ligands as minor species. Hopefully, the efficient and readily-accessible catalytic systems reported herein could demonstrate great potential for further practical applications.

7-Substituted Purine Derivatives for Immunosuppression

The present invention provides novel purinone and related derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formula III:

Thiazolyl-benzimidazoles

The invention is directed to compounds of formula (1) [image] and pharmaceutically acceptable salts thereof, methods for the preparation thereof, and methods of use thereof.