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CAS No. : | 939-70-8 | MDL No. : | MFCD00159994 |
Formula : | C9H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UYFMRVDIXXOWLR-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 70322 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.29 |
TPSA : | 45.75 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) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.77 |
Log Po/w (MLOGP) : | 0.67 |
Log Po/w (SILICOS-IT) : | 2.32 |
Consensus Log Po/w : | 1.5 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.21 mg/ml ; 0.00755 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.83 |
Solubility : | 2.37 mg/ml ; 0.0148 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.23 |
Solubility : | 0.0932 mg/ml ; 0.000582 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
85% | With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In water; acetonitrile at 10 - 15℃; for 0.5 h; | To a solution of 1 (1.62 g, 0.01 mol), 2,2,6,6-tetramethylpiperidin(0.016 g, 0.1 mmol) and potassium bromide(0.12 g, 1 mmol) in 40 mL acetonitrile/water (1:1), 8percent aqueoussodium hypochlorite (13.96 g, 0.015 mol) was added over a 15–20 min period, keeping the temperature of the reaction mixturebetween 10 and 15 C. The mixture was stirred for 30 min andwas extracted with ethyl acetate (50 mL 3). The combinedextracts were washed with 60 mL of 10percent aqueous sodium thiosul-fate and 60 mL of saturated sodium chloride solution. The organicphase was separated, dried over anhydrous MgSO4 and evaporatedto afford compound 2 with 85percent yield, MS (ESI) m/z: 161 (M+H)+. 1HNMR (400 MHz, DMSO) d 13.31 (s, 1H), 7.84 (d, J = 8.1 Hz, 1H), 7.57(d, J = 8.1 Hz, 1H), 7.39 (t, J = 7.1 Hz, 1H), 7.31 (d, J = 7.2 Hz, 1H),2.72 (s, 3H). |
70% | With sulfuric acid; potassium dichromate In water at 20℃; for 0.333333 h; | To a solution of 1-(1H-benzimidazol-2-yl)ethanol 1 (8.1 g,0.05 mol) in dilute sulphuric acid (40 ml), a solution ofpotassiumdichromate (9.8 g, 0.05 mol) in water (60 ml) wasadded at room temperature. To this mixture, concentratedsulphuric acid (20 ml) was added in a dropwise fashion,over a period of 20 min. The reaction mixture was stirredvigorously during addition. The separated solid was filteredand wash with water (30 ml). The precipitate obtained wasre-suspended in water (50 ml) and treated very carefullywith aqueous ammonia to obtain a pH 6.0–6.5. The suspensionwas stirred for 0.5 h and filtered. The residue 2 waswashed with water (3 × 10 ml) and dried. Yield = 70percent, m.p. 189–191 °C. IR (KBr) cm−1: 3358 (NH), 3024 (Ar-CH),2971 (CH3-CH), 1740 (C=O), 1647 (C=N), 1601 (C=C).1H-NMR (CDCl3, 500 MHz) δ ppm: 2.31 (s, 3H, CH3), 5.19(s, 1H, NH), 7.342–7.86 (m, 4H, Ar-CH). 13C-NMR(CDCl3, 500 MHz) δ ppm: 195.4 (C=O), 154.8 (C-2),140.5 (C-8 & C-9), 129.6 (C-5 & C-6), 117.2 (C-4 & C-7),29.7 (CH3). EI-MS m/z: 160 (M+). Anal. calcd forC9H8N2O: C, 67.49; H, 5.03; N, 17.49. Found: C, 67.68; H,5.04; N, 17.44. |
69% | at 80℃; | The method for synthesizing 2-acetylbenzimidazole in this example is as follows:2-Hydroxyethylbenzimidazole (0.1 mol, 16.2 g)The ruthenium complex Ru(bpbp)(pydic) (10-4 mol, 0.0730 g) in Example 3 was added to the reaction vessel.Hydrogen peroxide (30percent, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.Control the reaction temperature below 80 °C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Pure product 2-acetylbenzimidazole 11.0g was obtained. Yield 69percent. |
64% | With chromium(VI) oxide; acetic acid In water at 90 - 105℃; for 0.166667 h; | A 50 mL round bottom flask was added 5.4 g (0.05 mol) of o-phenylenediamine,4.5 g (0.05 mol) of lactic acid and 20 ml of 4 mol / L hydrochloric acid,Heating reflux 1.5h,Cool to room temperature.With concentrated ammonia and purple purple litmus paper turned red,Filter out the solid,Recrystallization from water (63percent).To a 50 mL three-necked flask, 2.24 g (0.02 mol) of 2- (α-hydroxy) ethylbenzimidazole and 15 mL of glacial acetic acid were added,After heating to 90 ° C, an aqueous solution of CrO3 was added dropwise to the three-necked flask,After dripping,The reaction was stirred at 105 ° C for 10 min,The reaction was then poured into a beaker containing 200 mL of water,Stirring for a moment,Filter,The filtrate was extracted three times with chloroform,The chloroform layers were combined,Dried over anhydrous magnesium sulfate,The filtrate was evaporated to dryness to give a yellow solid,Recrystallization from toluene,Yield: 64percent.To a 50 mL three-necked flask was added 1.6 g of 2-acetylbenzimidazole, 15 mL of 2 mol / L NaOH solution, and 1.3 mL of bromoethane was added to the flask,After the dropwise addition, the three-necked flask was quickly placed in an ice bath and cooled to 0 ° C,5min after precipitation of a large number of solid,Filter,Washed,Dried to obtain a yellow solid,Yield: 79percentTo a 50 ml round bottom flask was added 20 ml of 95percent ethanol and 3.20 g (0.02 mol) of 1- (1-ethyl-1H-benzimidazol-2-ethyl)Stir for about 10 min to completely dissolve the solid,Further, 8 ml of a 10percent aqueous solution of sodium hydroxide was added,0.02 mol of 2-pyridinecarbaldehyde was added with stirring,After a period of time the system precipitates a lot of solid,The reaction end point was detected by TLC,After the reaction, the filtrate was filtered to obtain a solid, yield: 86percent |
57% | With Ru(2,6-bis(1-(phenyl)-1H-benzo[d]imidazol-2-yl)pyridine)(pbb)Cl; dihydrogen peroxide In water at 50℃; for 5 h; | (1H-benzo[d]imidazol-2-yl)ethanol (0.1 mol, 14.8 g) and Ru(bpbp)(pbb)Cl(0.001mmol, 7.32 × 10−3 g) were added into a reactor. Thereactor containing this mixture was heated to 50 °C in an oilbath under vigorous stirring, and then 30percent H2O2 (30 mL,0.3mol) was slowly dropped into the reactor in 30min. Themixture was stirred for 5h. After filter, the solution wasevaporated under reduced pressure at 50 °C. After extractionwith CH2Cl2, the crude product was chromatographed onsilica gel (eluent: CH2Cl2). Pure 1-(1H-benzo[d]imidazol-2-yl)ethanone (0.07mmol, 10.2 g) was obtained with the isolated yield of 57percent by removing the solvent. The productwas identified by 1HNMR spectrum (400MHz, CDCl3)(Figure 5) and IR spectrum (Figure 6), which are all inagreement with the assumed structure. IR is also same withthe standard Bio-Rad/Sadtler IR Data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 0 - 20℃; for 2.25 h; Inert atmosphere | To a stirred solution of compound 190 (15 g, 73.13 mmol) in anhydrous THF (200 mL) under inert atmosphere was added methyl magnesium bromide (48.75 mL, 146.3 mmol, 3 M sol. in diethyl ether) dropwise for 15 min at 0 oC. The reaction mixture was stirred at 0 oC for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford compound 191 (7g, 60percent) as a yellow solid. TLC: 30percent EtOAc/ hexanes (Rf: 0.5); 1H NMR (400 MHz, DMSO-d6): δ δ 13.28 (s, 1H), 7.82-7.80 (m, 1H), 7.55-7.53 (m, 1H), 7.35-7.30 (m, 2H), 2.69 (s, 3H); LCMS Calculated for C9H8N2O: 160.06; Observed: 160.95 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With manganese dioxide In hydrogenchloride; CH2Cl2/MeOH | Preparation of 1-(1H-Benzimidazol-2-yl)-ethanone: A solution of 1,2-phenylene diamine (3.25 g, 0.030 mol) and L-lactic acid (2.3 mL, 0.026 mol) in 3 M HCl (15 mL) was refluxed overnight. The reaction was cooled to room temperature, diluted with EtOAc (50 mL) and saturated aqueous Na2CO3 and solid Na2CO3 to pH 10. The aqueous phase was washed with EtOAc (1*50 mL) and the combined organic extracts dried (Na2SO4) and concentrated to afford a brown-orange solid which was used in the next reaction without further purification. To a stirred solution of the crude alcohol from above (0.026 mol) in dry CH2Cl2/MeOH (6:1, 35 mL) was added activated manganese dioxide (85percent purity, <5 micron, 23.28 g, 0.228 mol) and the suspension stirred overnight, at which point the black slurry was filtered through a cake of celite and washed with MeOH (3*50 mL). The combined washings were concentrated to afford a dark brown solid. Purification of the crude product by column chromatography on silica gel (CH2Cl2MeOH, 98:2 to 95:5) afforded the title compound as a red-brown solid (1.65 g, 39percent). 1H NMR (CD3OD) δ 2.72 (s, 3H), 7.37 (dd, 2H, J=6, 3 Hz), 7.66-7.73 (br m, 2H). |
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