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CAS No. : | 5381-20-4 | MDL No. : | MFCD00052376 |
Formula : | C9H6OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WDJLPQCBTBZTRH-UHFFFAOYSA-N |
M.W : | 162.21 | Pubchem ID : | 227328 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.21 |
TPSA : | 45.31 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) : | -5.47 cm/s |
Log Po/w (iLOGP) : | 1.76 |
Log Po/w (XLOGP3) : | 2.56 |
Log Po/w (WLOGP) : | 2.71 |
Log Po/w (MLOGP) : | 1.81 |
Log Po/w (SILICOS-IT) : | 3.81 |
Consensus Log Po/w : | 2.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.0 |
Solubility : | 0.163 mg/ml ; 0.001 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.16 |
Solubility : | 0.112 mg/ml ; 0.000693 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.28 |
Solubility : | 0.0851 mg/ml ; 0.000525 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
55% | With trifluorormethanesulfonic acid; trimethylsilylazide In acetonitrile at 20℃; for 0.333333 h; Sealed tube; Inert atmosphere | General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20–75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: at 0℃; for 1 h; Stage #2: With carbon tetrabromide; triphenylphosphine In dichloromethane for 1 h; Inert atmosphere |
To a solution of l-benzothiophene-5-carbaldehyde (800 mg, 5 mmol) in MeOH (10 mL) was added sodium tetrahydroborate (0.28 g, 7.4 mmol) at 0 °C. The reaction mixture was allowed to stir at 0 °C for lh, at which point a saturated aqueous solution of H4C1 (50 mL) and water (50 mL) was added. The mixture was extracted with DCM (3x). The organic solutions were combined, dried over MgS04, filtered, and concentrated to dryness. The crude solid was then dissolved in DCM (100 mL) under argon and triphenyl phosphine (2.30 g, 8.78 mmol) and carbon tetrabromide (2.0 g, 5.9 mmol) were added. After stirring for lh, diethyl ether was added and the resulting mixture was filtered and washed with diethyl ether (2x). The filtrate was concentrated to dryness and the crude residue was purified by column chromatography to afford 5-(bromomethyl)-l-benzothiophene (760 mg, 70 percent) as a white solid. 1H MR (400 MHz, CDCI3) δ 7.80 - 7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.41 (dd, J=8.3, 1.8 Hz, 1H), 7.35 (d, J=5.4 Hz, 1H), 4.68 (s, 2H). |
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