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CAS No. : | 22053-74-3 | MDL No. : | MFCD00052307 |
Formula : | C10H8OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRZGHNXLEQHVHB-UHFFFAOYSA-N |
M.W : | 176.23 | Pubchem ID : | 519918 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.18 |
TPSA : | 45.31 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.17 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 3.1 |
Log Po/w (WLOGP) : | 3.02 |
Log Po/w (MLOGP) : | 2.11 |
Log Po/w (SILICOS-IT) : | 4.25 |
Consensus Log Po/w : | 2.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.37 |
Solubility : | 0.0744 mg/ml ; 0.000422 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.72 |
Solubility : | 0.0336 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.67 |
Solubility : | 0.0372 mg/ml ; 0.000211 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
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 |
---|---|---|
100% | Stage #1: 3-methylbenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -69℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane for 1h; Reflux; | 3-Methylbenzo[b]thiophene-2-carbaldehyde, 6 To a solution of compound 5 (4.87 g; 30.1 mmol) in anhydrous THF (50 mL), cooled to -69 °C, was added a solution of 2.5 M n-butyllithium in hexanes (14.4 mL; 36.0 mmol), dropwise. The reaction was allowed to stir at -69 °C for 1 h, to which was then added anhydrous DMF (5.0 mL; 64.5 mmol), dropwise. The reaction was allowed to warm to ambient temperature, and was then refluxed for 1 h. At that time, the reaction was cooled, diluted with EtOAc, washed sequentially with H2O, brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford 5.36 g (100%) of compound 6 as a white solid. 1H-NMR (300 MHz, DMSO-d6): 10.34 (s, 1H), 7.85-7.90 (m, 2H), 7.42-7.53 (m, 2H), 2.79 (s, 3H). |
78% | Stage #1: 3-methylbenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 1h; | 3-Methylbenzo[b]thiophene-2-carbaldehyde (1a1); Typical Procedurefor Step 1 (Scheme 4) To a solution of 3-methylbenzothiophene (1.00 g, 7.45 mmol) in anhydrous THF (35 mL) cooled at -78 °C was added dropwise n-BuLi(5.12 mL, 1.6 M in hexane, 8.20 mmol). After stirring for 1 h at -78 °C, DMF (1.15 mL, 14.90 mmol) was added dropwise and the reaction continued for 1 h. The reaction mixture was quenched by the additionof sat. aq NH4Cl. The aqueous phase was extracted with EtOAc and the organic phase was washed with brine, dried (Na2SO4), and concentrated. The purification of the residue by column chromatography (hexane/EtOAc, 95:5) afforded 1a1 as a pale yellow solid; 22 yield: 853mg (78%); mp 87-89 °C; Rf = 0.7 (hexane/EtOAc 8:2). IR (KBr): 2915, 1651, 1529, 1377, 1265, 1212, 1074, 936 cm-1. 1H NMR (400 MHz, CDCl3): δ = 10.36 (s, 1 H), 7.92-7.88 (m, 2 H), 7.54(td, J = 7.5, 1.2 Hz, 1 H), 7.49-7.45 (m, 1 H), 2.81 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 184.0, 143.0, 142.0, 140.0, 137.5,128.4, 124.8, 123.9, 123.3, 12.1. HRMS (ESI): m/z (M + H)+ calcd for C10H9OS: 177.0374; found:177.0349. |
73% | With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere; | 5.5. General procedure D for the aldehyde preparation according tothe n-BuLi 2-deprotonation/DMF electrophilic trapping General procedure: To a solution of the (benzo)thiophene derivative (2.30 mmol) inanhydrous THF (4 ml) under argon at 78 C was added dropwise a2.5 M solution of n-BuLi in hexanes (1.00 ml, 2.50 mmol). The reactionmixture was stirred for 1 h at 78 C and DMF (0.25 ml,3.20 mmol) was then added. The resulting mixture was allowed tostand 2 h at room temperature and then poured into water (10 ml)and extracted three times with ethyl acetate (3 20 ml). Theorganic phase was washed with H2O (20 ml), dried with Na2SO4and the volatiles were removed under reduced pressure. The crudeproduct was then purified by flash chromatography (AcOEt/cyclohexane)on silica gel. |
Stage #1: 3-methylbenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -69℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -69℃; for 1h; Reflux; | 1.A A. 3-Methyl-benzo[b]thiophene-2-carboxyaldehyde. To a solution of 3-methyl-benzo[b]thiophene (Compound 1a) (4.87 g; 30.1 mmol) in anhydrous THF (50 mL), cooled to -69° C., was added a solution of 2.5 M n-butyllithium in hexanes (14.4 mL; 36.0 mmol), dropwise. The reaction was allowed to stir at -69° C. for 1 h, to which was then added anhydrous DMF (5.0 mL; 64.5 mmol), dropwise. The reaction was allowed to warm to ambient temperature, and was then refluxed for 1 h. At that time, the reaction was cooled, diluted with EtOAc, washed sequentially with H2O and brine, and dried over Na2SO4. The mixture was filtered and the solvent evaporated under reduced pressure to afford Compound 1b. 1H-NMR (300 MHz, DMSO-d6): δ 10.34 (s, 1H), 7.85-7.90 (m, 2H), 7.42-7.53 (m, 2H), 2.79 (s, 3H). | |
Stage #1: 3-methylbenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -69℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 1h; Reflux; | 1.A A. 3-Methyl-benzo[b]thiophene-2-carboxyaldehyde. To a solution of 3-methyl-benzo[b]thiophene (Compound 1a) (4.87 g; 30.1 mmol) in anhydrous THF (50 mL), cooled to -69° C., was added a solution of 2.5 M n-butyllithium in hexanes (14.4 mL; 36.0 mmol), dropwise. The reaction was allowed to stir at -69° C. for 1 h, to which was then added anhydrous DMF (5.0 mL; 64.5 mmol), dropwise. The reaction was allowed to warm to ambient temperature, and was then refluxed for 1 h. At that time, the reaction was cooled, diluted with EtOAc, washed sequentially with H2O and brine, and dried over Na2SO4. The mixture was filtered and the solvent evaporated under reduced pressure to afford Compound 1b. 1H-NMR (300 MHz, DMSO-d6): δ 10.34 (s, 1H), 7.85-7.90 (m, 2H), 7.42-7.53 (m, 2H), 2.79 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-methylbenzo[b]thiophene-2-carboxaldehyde; 2-ethynyl-5-methylthiophene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 77℃; |