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CAS No. : | 27080-53-1 | MDL No. : | MFCD11973699 |
Formula : | C8H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KEINCPBIVGNTSZ-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 14970878 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.59 |
TPSA : | 37.91 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.17 cm/s |
Log Po/w (iLOGP) : | 1.28 |
Log Po/w (XLOGP3) : | 1.46 |
Log Po/w (WLOGP) : | 1.57 |
Log Po/w (MLOGP) : | 0.7 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.22 |
Solubility : | 0.897 mg/ml ; 0.00606 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.86 |
Solubility : | 2.03 mg/ml ; 0.0137 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.02 |
Solubility : | 0.142 mg/ml ; 0.000959 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 72 h; Inert atmosphere | General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt percent, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10percent MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99percent). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.9% | for 4 h; Reflux | The reaction mixture of 3-methoxy-o-phenylenediamine (2, 190mg, 1.37mmol)and HCOOH (5mL) was refluxed for 4h, then cooled to room temperature and poured into ice/ water (20mL). The mixture was treated with 10percent NaOH aqueous solution to pH≈8 and then extracted with ethyl ether (15mL×3). The combined extracts were washed with water and brine, then dried over anhydrous MgSO4. The organic phase was concentrated to give the crude product, which was purified by column chromatography with CH2Cl2–MeOH (v/v=60/1). The desired product 4-methoxy-1H-benzo[d]imidazole (162mg) was afforded as white powder with 83.9percent yield. M.p. 165–167°C; 1H NMR (acetone-d6, 300MHz, δ ppm): 8.08 (1H, s), 7.21 (1H, d, J=7.8Hz), 7.11 (1H, t, J=7.8Hz), 6.73 (1H, d, J=7.8Hz), 3.97 (3H, s); HRMS (ESI): m/z, calcd. For C8H9N2O [M+H]+ 149.0709 found 149.0707. |
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