Structure of 38695-60-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 38695-60-2 |
Formula : | C5H6O2S2 |
M.W : | 162.23 |
SMILES Code : | O=S(C1=CC=CS1)(C)=O |
MDL No. : | MFCD00052826 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319-H302 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 37.41 |
TPSA ? Topological Polar Surface Area: Calculated from |
70.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.38 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.23 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.43 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.84 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.43 |
Solubility | 6.02 mg/ml ; 0.0371 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.43 |
Solubility | 6.01 mg/ml ; 0.037 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.97 |
Solubility | 1.75 mg/ml ; 0.0108 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.02 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.54 |
* 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 |
---|---|---|
40% | With 7H-benz<c>thioxanthen-7-one; oxygen; In acetonitrile; at 20℃;Sealed tube; Irradiation; | General procedure: A solution of sulfides 1 (0.2 mmol, 1.0 equiv) or sulfoxides 2 (0.2 mmol, 1.0 equiv), photocatalyst (c, 5 mol%), and ACN (1 mL, 0.2 M) was sealed in an oven-dried reaction tube equipped with an oxygen balloon (gas-switch three times with oxygen balloon). The reaction was agitated under 18 W 405 nm LEDs at room temperature for 12 to 24 h. The progress of the reaction was monitored by GC-MS or/and TLC. After completion of the reaction, the solvent was removed under reduced pressure, and the crude product 3 was purified by flash silica chromatography using n-hexane and ethyl acetate as eluent (v/v, 80:20). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | A solution of methyl thienyl sulfone (1.00 g, 6.16 mmol) in THF (14 mL) was added dropwise to a stirred suspension of NaH (0.2 g of a 80% dispersion in oil, 6.8 mmol) inTHF (1 mL) at room temperature. After 30 min, a solution of 2-iodobenzyl chloride (1.56 g, 6.16 mmol) in THF (15 mL) was added and the resulting mixture stirred for 48 h. The reaction mixture was heated at reflux for 48 h more. After cooling, the reaction mixture was poured into water and extracted with ether (3 x 25 mL). The combined organic extract was washed with brine, dried (MgSO4) and concentrated. Purification of the residue by chromatography (petrol / ether, 6:4 to 4:6) gave, in order of elution, 2-(2-iodophenyl)ethyl thienylsulfone, 99, (0.71 g, 30%) as colourless needles. (mp 99-101C, CH2Cl2/petrol). Found C 38.2, H 2.9. C12H11IO2S2 requires C 38.1, H 2.9%. νmax (NaCl/film)/cm-1 3090, 1564, 1468, 1442, 1402, 1317, 1229, 1137, 1093, 1014, 856, 749; δH(400 MHz): 3.18 (2 H, m, CH2Ar), 3.45 (2 H, m, CH2S), 6.92 (1 H, dt, J 7.8 and 1.9, H-4), 7.19 (1 H, dd, J 4.8 and 3.8, H-4'), 7.22 (1 H, dd, J 7.8 and 1.9, H-6), 7.28 (1H, dt, J 7.5 and 1.4, H-5), 7.76 (1 H, dd, J 5.1 and 1.4, H-5'), 7.77 (1 H, dd, J 7.8 and 1.4, H-3), 7.78 (1 H, dd, J 3.8 and 1.3, H-3'); δC (100.6 MHz): 34.7 (CH2), 57.1 (CH2S), 99.8 (C), 128.0 (CH), 128.9 (CH), 129.0 (CH), 129.9 (CH), 134.3 (CH), 134.6 (CH), 139.6 (C), 139.8 (CH), 139.9 (C); m/z: 378 (M+, 1), 251 (41), 231 (20), 230 (100), 131 (18), 104 (60), 103 (70), 102 819), 78 (31), 77 (70); and starting methyl thienyl sulfone (0.49 g, 49%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In water; at 100℃; for 10h;Sealed tube; | In the reflux reactor,Followed by adding 0.5mmlSodium 2-thienylsulfinate,1 mmol di-tert-butyl peroxide,2.5mL water; magnetic stirring, heat sealed at 100 for 10 hours;After stopping heating, cool to room temperature and then use ethyl acetateThe reaction mixture was extracted three times; the ethyl acetate was removed under reduced pressure to obtain the target 2-thienylmethylsulfone.The structure of the resulting product was confirmed by GC-MS, 1H NMR, 13C NMR.The yield of 2-thienylmethylsulfone was 89% |
89% | With water; at 110℃; for 12h;Sealed tube; Green chemistry; | General procedure: Sodium benzenesulfinate (0.5 mmol), 2-(tert-butylperoxy)-2-methylpropane (1 mmol), and H2O (2.5 mL) were added into a 10 mL sealed tube successively. Then, the reaction was carried out at 110 C under magnetic stirring for 12 h. After the reaction was finished, the reaction mixture was extracted with ethyl acetate for three times (5 mL × 3). The obtained organic layer was dried with anhydrous MgSO4. The solvent was removed under vacuum, and the obtained crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10:1) as eluent to afford the desired pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In water; at 50℃; for 16h;Sealed tube; | In a reflux reactor, 0.5 mml of sodium 2-thienylsulfinate, 1.5 mmol of di-tert-butyl peroxide,2.5mL of water; magnetic stirring, heating sealed at 50 for 16 hours; to stop heating, cooled to room temperature, and then with ethyl acetateThe reaction mixture was extracted three times; the ethyl acetate was removed under reduced pressure distillation to obtain the target product 2-methyl-1- (2-thiophene-phenylsulfonylYl) -2-propanol.The structure of the resulting product was confirmed by GC-MS, 1H NMR, 13C NMR and IR. 2-Methyl-1- (2-thiophenbenzenesulfonylYl) -2-propanol was isolated in 82% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide; In water; acetonitrile; at -30 - 20℃; for 0.5h;Inert atmosphere; Resolution of racemate; | General procedure: Mn(OTf)2 (1.4 mg, 0.004 mmol) and L2 (2.0 mg, 0.004 mmol) were dissolved in acetonitrile, and the mixture was stirred at room temperature for 12 h. To the solution of manganese complex were added substrate (0.4 mmol), 0.2 equiv of aca (14.4 mg, 0.08 mmol), and 49 % aqeous hydrogen peroxide (56.5 mg, 0.4 mmol). Then decreased the temperature to -30 C, and the reaction mixture was stirred at -30 C for 0.5 h. The aqueous was separated, the organic layer was dried over MgSO4, filtered, concentrated at reduced pressure. The product was purified by silica gel column chromatography to afford the corresponding sulfoxide and sulfone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium phosphate; copper(l) iodide; C16H18N2O2; In dimethyl sulfoxide; at 120℃;Schlenk technique; Inert atmosphere; | General procedure: Sodium alkylsulfinate or sodium arylsulfinate (6.5 mmol), copper iodide (0.5 mmol), ligand (0.5 mmol) and potassium phosphate (5.0 mmol) were added into a 10 mL Schlenk tube. The tube was evacuated and filled with argon for three times, and then aryl chloride (5 mmol) and 3 mL of DMSO were added. The reaction mixture was homogeneously stirred at 120 C. for 24-36 hours. After cooling, the contents of the of Schlenk tube were washed with ethyl acetate, and filtered through silica gel and diatomite plug. The filtrate was concentrated and purified by column chromatography to give the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With bis-triphenylphosphine-palladium(II) chloride; 1,1,3,3-Tetramethyldisiloxane; tetrabutylammomium bromide; In 1,4-dioxane; at 120℃; for 18h;Inert atmosphere; | 105.0 mg (0.5 mmol) of 2-iodothiophene, 550.3 mg (5 mmol) of dimethyl sulfite, 35.1 mg (0.05 mmol) of bistriphenylphosphorus palladium (II) dichloride, 100.7 mg (0.75 mmol) 1,1,3,3- tetramethyl disiloxane, 161.3 mg (0.5 mmol) of tetrabutylammonium bromide to the reaction tubes, 120OC was heated for 18 hours after the reaction was cooled, The filtrate was filtered and the filtrate was evaporated to remove the solvent. The residue was subjected to silica gel column chromatography, eluted with petroleum ether, TLC detection, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator and dried under vacuum to obtain 43.8 mg of white solid 2-methyl. Sulfonylthiophene, the yield is 54%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With sodium iodide; In 1,2-dimethoxyethane; water; at 65℃; | General procedure: To a 10 mL round-bottom flask were added sulfonylhydrazine 1 (1.0 mmol), dimethyl phosphite 2 (0.6 mmol) and NaI (0.2 mmol) in mixed solvent DMF/H2O (10:1, v/v; 3 mL), and the solution was stirred for 5-10 h at 65 C until sulfonylhydrazine 1 was completely consumed as indicated by TLC analysis. The crude products were then concentrated under reduced pressure, and purified by flash column chromatography (petroleum ether/EtOAc = 30:1 to 10:1), to obtain pure products 3, 6 and 7 with 54-95% yield. |