Identification | More | [Name]
5,6-DICHLOROBENZIMIDAZOLE | [CAS]
6478-73-5 | [Synonyms]
1H-BENZIMIDAZOLE, 5,6-DICHLORO- 5,6-DICHLORO-1H-1,3-BENZIMIDAZOLE 5,6-DICHLORO-1H-BENZIMIDAZOLE 5,6-DICHLORO-1H-BENZO[D]IMIDAZOLE 5,6-DICHLOROBENZIMIDAZOLE BUTTPARK 121\15-71 NSC 326397 NSC 6393 1H-Benzimidazole,5,6-dichloro-(9CI) NSC 63938 | [Molecular Formula]
C7H4Cl2N2 | [MDL Number]
MFCD00211325 | [Molecular Weight]
187.03 | [MOL File]
6478-73-5.mol |
Chemical Properties | Back Directory | [Appearance]
Purple Solid | [Melting point ]
205-206° | [Boiling point ]
426.9±25.0 °C(Predicted) | [density ]
1.571±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
10.74±0.30(Predicted) | [color ]
Tan to Light Beige | [Usage]
A benzimidazole derivative as potent inhibitor of milk xanthine oxidase | [CAS DataBase Reference]
6478-73-5(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 |
Hazard Information | Back Directory | [Chemical Properties]
Purple Solid | [Uses]
A benzimidazole derivative as potent inhibitor of milk xanthine oxidase | [Uses]
A benzimidazole derivative as potent inhibitor of milk xanthine oxidase. | [Synthesis]
General procedure for the synthesis of 5,6-dichlorobenzimidazole from N-benzylbenzimidazole (CAS:6478-78-0, 208.1 mg, 1.0 mmol): to a 16 mL reaction flask equipped with a PTFE/silicone septum and a nitrogen bubbling device under nitrogen protection were added N-benzylbenzimidazole, a dry Pd/C catalyst (10 wt%. 20 mg) and THF (5 mL). Subsequently, triethylsilane (320 μL, 2.0 mmol) was slowly added to the reaction mixture at room temperature and stirred continuously for 14 h under nitrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered through a 0.45 μm PTFE syringe filter to remove the catalyst and the filtrate was concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography (eluent: 0 to 10% MeOH/dichloromethane gradient) to afford the target product 5,6-dichlorobenzimidazole as a colorless solid (117.6 mg, 0.996 mmol, 99% yield). It is worth noting that an induction period of 5 to 30 min usually exists at the beginning of the reaction, which is manifested by the beginning of gas release from the reaction mixture (i.e., the bubbling phenomenon). In addition, the use of a dry Pd/C catalyst is critical to the success of the reaction; wet Pd/C may result in a significant decrease in the reaction yield or no reaction at all. | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690 |
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