| Identification | More | [Name]
5-METHOXYBENZIMIDAZOLE | [CAS]
4887-80-3 | [Synonyms]
5-METHOXY-1H-BENZIMIDAZOLE
5-METHOXYBENZIMIDAZOLE
BUTTPARK 146\15-76
5-Methoxybenzimidazole,99%
1H-Benzimidazole,5-methoxy-(9CI) | [EINECS(EC#)]
225-502-9 | [Molecular Formula]
C8H8N2O | [MDL Number]
MFCD00272526 | [Molecular Weight]
148.16 | [MOL File]
4887-80-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White to brown powder | [Melting point ]
121-126 °C (lit.) | [Boiling point ]
190-195 °C(Press: 0.03 Torr) | [density ]
1.244±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
solid | [pka]
13.12±0.10(Predicted) | [color ]
Light brown to brown | [InChI]
InChI=1S/C8H8N2O/c1-11-6-2-3-7-8(4-6)10-5-9-7/h2-5H,1H3,(H,9,10) | [InChIKey]
ILMHAGCURJPNRZ-UHFFFAOYSA-N | [SMILES]
C1NC2=CC(OC)=CC=C2N=1 | [CAS DataBase Reference]
4887-80-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29332990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to brown powder | [Uses]
6-Methoxy-1H-benzimidazole has been studied for its anti-proliferative activity, and a preliminary in vivo toxicity study against a panel of non-small cell lung cancer cell lines. | [Synthesis]
To a 16 mL reaction flask equipped with a PTFE/silicone septum and a nitrogen bubbler was added N-benzylbenzimidazole (208.1 mg, 1.0 mmol), dried Pd/C catalyst (10 wt%, 20 mg) and THF (5 mL). Triethylsilane (320 μL, 2.0 mmol) was added dropwise to the mixture under nitrogen protection, followed by continuous stirring at room temperature for 14 hours. After completion of the reaction, the reaction mixture was filtered through a 0.45 μm PTFE syringe filter and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: 0 to 10% methanol/dichloromethane gradient) to afford 5-methoxybenzimidazole as a colorless solid (117.6 mg, 0.996 mmol, 99% yield). It is worth noting that the reaction typically suffers from an induction period of 5 to 30 min, which can be observed by the release of gas from the reaction mixture (i.e., the bubbling phenomenon). The use of a dry Pd/C catalyst is critical to the success of the reaction, and wet Pd/C may result in a significant decrease in yield or inability of the reaction to proceed. | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690 |
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