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CAS No. : | 7152-24-1 | MDL No. : | MFCD00005594 |
Formula : | C8H8N2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OCKJFOHZLXIAAT-UHFFFAOYSA-N |
M.W : | 164.23 | Pubchem ID : | 23539 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.81 |
TPSA : | 53.98 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) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 1.56 |
Log Po/w (XLOGP3) : | 2.1 |
Log Po/w (WLOGP) : | 2.28 |
Log Po/w (MLOGP) : | 1.58 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.72 |
Solubility : | 0.312 mg/ml ; 0.0019 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.225 mg/ml ; 0.00137 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.4 |
Solubility : | 0.0655 mg/ml ; 0.000399 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | 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 |
---|---|---|
97% | With 1,3,5-trichloro-2,4,6-triazine; dihydrogen peroxide; In water; acetonitrile; at 20℃; for 0.333333h; | General procedure: To a mixture of sulfide (1 mmol) and TCT (1 mmol, 0.184 g) in acetonitrile (5 mL) was added 30% H2O2 (2 mmol, 0.2 mL). The mixture was stirred at room temperature for the appropriate period of time until complete consumption of the starting material as observed by TLC. After completion of the reaction, H2O (10 mL) was added to the reaction mixture which was then extracted with EtOAc (4 × 5 mL) and the combined extracts were dried (MgSO4). The filtrate was evaporated and the corresponding sulfone was obtained as the only product (Table 1). |
15.5 g (89%) | With oxone; In methanol; water; | Step 1) Preparation of 2-(Methylsulfonyl)-1H-benzimidazole According to the procedure of B. M. Trost, et al., Tetrahedron Lett., 22 (14), 1287 (1981), to a cooled (0 C.), stirred solution of <strong>[7152-24-1]2-(methylthio)benzimidazole</strong> (14.5 g, 0.088 mol) in MeOH (350 mL) was added a solution of oxone (2 KHSO5.KHSO4.K2 SO4; 81.6 g, 0.133 mol) in H2 O (350 mL) over 10 minutes. The cooling bath was removed after 10 minutes, stirring was continued at room temperature for 5 hours. The MeOH was removed under reduced pressure and the white solid was collected by filtration to give 15.5 g (89%) of product m.p. 200-202 C. NMR (DMSO-d6, 300 MHz): delta3.50 (s, 3H), 7.40 (dd, J=6.2 Hz, 3-1 Hz, 2H), 7.72 (brs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In decane; dichloromethane; at 20℃; | t-BuOOH (solution 5.5 M in decane, 1 mL) and V0(acac)2 (5%, 0.25 mmol, 66 mg)were added in sequence to a solution of commercially available 2-(methylthio)-benzoimidazole (5 mmol, 820 mg) in CH2Cl2 (25 ml). The mixture was stirred at rt and monitored by thin-layer chromatography (TLC). At the end of there action, the solventwasremovedunderreducedpressureandthecrudewasdirectlypurifiedby flashchromatography (CHCl3/EtOAc) to obtain pure 1 as a white solid (765 mg, 4.2 mmol, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Compound 42 was prepared using the same procedure as compound 4 with compound 42d and 2-(methylmercapto)benzimidazole in 95% yield: 1H NMR (CD3OD) delta 0.99 (d, J=6.5 Hz, 6H), 1.61-1.66 (m, 2H), 1.66-1.71 (m, 1H), 2.91 (s, 3H), 4.40-4.43 (m, 2H), 6.05 (s, 2H), 7.21 (td, J=2.4, 9.2 Hz, 1H), 7.27 (dd, J=2.4, 8.9 Hz, 1H), 7.43-7.51 (m, 2H), 7.63-7.65 (m, 2H), 7.76 (d, J=7.8 Hz, 1H); MS m/e 384 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25 - 45% | With potassium tert-butylate; In N,N-dimethyl-formamide; at 80℃; | To a stirred solution of a benzimidazole g (beta.OOmmols) and p- <n="137"/>fluoronitrobenzene h (6.00mmols) in 1OmL of anhydrous DMF, was added [potassium t-butoxide (f-BuOK) (7.61 mmols, 1.25eq.), and the reaction mixture was stirred at 80 0C overnight. The reaction mixture was added into 5OmL of water and the product was extracted with ethylacetate (3 x 2OmL). The extracts were washed with brine and concentrated. Column chromatography on silica gel using mixture of hexane:ethylacetate provided compound i in 25-45% yields.To a stirred solution of compound i (1.31 mmols) in 2OmL of 1 :1 CH2CI2IEtOH, was added SnCb (13.06mmols) followed by a few drops of water. The mixture was stirred overnight and concentrated. 2OmL of water was added to the residue, and the solution the brought to pH ~ 8-9 using 2N NaOH. The resulting mixture was extracted with ethylacetate (2OmL x 4), washed with brine (2OmL), dried over Na2SO-I, and concentrated to afforded compound j in 70-97% yields.To a solution of compound j (0.30mmols) in 5mL of CH2CI2, was added an acyl chloride k (0.30mmols), followed by diisopropyl-ethylamine (0.60mmols). The resultant mixture was stirred at room temperature for 30min and eluted through a short pad of silica gel using mixture of hexane:ethylacetate to afford, upon concentration, the product I in 80-96% yields. |
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