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CAS No. : | 13781-53-8 | MDL No. : | MFCD00005471 |
Formula : | C6H5NS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GWZCLMWEJWPFFA-UHFFFAOYSA-N |
M.W : | 123.18 | Pubchem ID : | 83730 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 33.84 |
TPSA : | 52.03 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.16 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 1.26 |
Log Po/w (WLOGP) : | 1.81 |
Log Po/w (MLOGP) : | 0.75 |
Log Po/w (SILICOS-IT) : | 2.8 |
Consensus Log Po/w : | 1.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.79 |
Solubility : | 1.98 mg/ml ; 0.0161 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.95 |
Solubility : | 1.38 mg/ml ; 0.0112 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.11 |
Solubility : | 0.952 mg/ml ; 0.00773 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
67% | With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 16 h; Inert atmosphere | This compound was synthesized according to a procedure described in literature.5 An oven-dried round-bottom flask (25 mL) cooled under argon was fitted with a rubber septum and charged with a stir bar, anhydrous InCl3 (0.681 g, 3.079 mmol), anhydrous THF (10 mL), and NaBH4 (0.341 g, 9.014 mmol). The reaction was stirred at 25 °C for 1h, followed by the dropwise addition of 3-thiopheneacetonitrile (0.340 mL, 2.981 mmol), and the mixture was stirred at 25 °C for 16 h. The solution was quenched with 10 mL of 2.8 M hydrochloric acid, and the solution was refluxed for 2 h to dissolve remaining metal salts. The reaction mixture was cooled to 25°C, 5 mL of methanol were added, and the mixture was again refluxed for 2 h. The reaction mixture was then cooled to 25°C and filtered, and the methyl borate/methanol was removed from the filtrate by evaporation. The remaining acidic solution was extracted with DCM (3 10 mL), and the organic layers were discarded. The acidic aqueous layer was then basified with NaOH pellets to pH ≈ 11 and again extracted with DCM (3 10 mL). The combined organic layers were dried on a WA filter filtered, and evaporated under vacuum to afford 2-(3-thienyl)ethanamine 7. Yellowish oil; 0.250 g, yield: 67percent. 1H NMR (300 MHz, CDCl3): δ = 7.20-7.30 (m, 1H; ArH), 7.00 (m, 1H; ArH), 6.95 (m, 1H; ArH), 2.96 (t, 2H; J = 6.6 Hz, CH2), 2.78 (t, 2H; J = 6.6 Hz, CH2), 1.45 ppm (bs, 2H; NH2). The 1H NMR spectrum was according to literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.06 g | With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 0 - 20℃; Inert atmosphere | NBS (9.07 g, 50.9 mmol, 1 equiv) and AIBN (836 mg, 5.1 mmol, 0.1 equiv) were added to a solution of 3-methylthiophene (5 g, 50.9 mmol, 1 equiv) in CCl4 (20 mL). The resulting mixture was refluxed for 1 h. After cooling, the solvent was evaporated under reduced pressure and the residue obtained was dissolved in dry acetonitrile (40 mL). To this solution, TMSCN (20 mL, 153 mmol, 3 equiv) and TBAF (1 M in THF, 153 mL, 153 mmol, 3 equiv) were added dropwise at 0 °C under argon atmosphere. After stirring overnight at room temperature, the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography (5percent EtOAc/cyclohexane) affording 5 as an orange oil (4.06 g, 33 mmol, 65percent for the two steps). 1H NMR (300 MHz, CDCl3): δ 7.22 (dd, J=5.0, 3.0 Hz, 1H), 7.10 (dd, J=2.8, 1.1 Hz, 1H), 6.90 (dd, J=5.0, 1.2 Hz, 1H), 3.58 (s, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ 129.4, 127.0, 126.9, 122.9, 117.7, 18.4 ppm. IR (neat): ν 3104, 2360, 2340, 2255, 1688, 1415, 832, 771, 692 cm−1. GC–MS: m/z C6H5NS [M+⩽] 122.#10; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: With borane-dimethyl sulfide In tetrahydrofuran for 16 h; Reflux Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.333333 h; |
Thiophen-3-yl-acetonitrile (2.0 g, 16.2 mmol)Soluble in tetrahydrofuran (36mL),The borane-dimethyl sulfide complex (3.0 mL, 30.4 mmol) was slowly added, and the reaction mixture was heated to reflux for 16 hours. At room temperature, the reaction was quenched by the slow addition of methanol.Then add saturated hydrogen chloride / methanol solution (10mL),Stir at room temperature for 20 minutes, concentrate to give a solid initial product.Wash with diethyl ether (20 mL).The compound 41A was obtained as a white solid (2.5 g, yield: 94percent). |
94% | Stage #1: With dimethylsulfide borane complex In tetrahydrofuran for 16 h; Heating / reflux Stage #2: With methanol In tetrahydrofuran |
Preparation 1; 2-Thiophene-3-yl-ethylamine hydrochloride; Slowly add borane methyl sulfide complex (30.4 mL, 304.4 mmol) to a solution of thiophen-3-yl-acetonitrile (25.0 g, 203.0 mmol) in tetrahydrofuran (450 mL). Heat the reaction at reflux for 16 h and then cool to RT. Slowly quench the reaction with methanol (50 mL) until no foaming is observed. To this mixture slowly add methanol (100 mL) which is saturated with hydrogen chloride. Stir the mixture at RT for 20 min before concentrating in vacuo. Add methanol (100 mL) to the mixture and concentrate in vacuo. Suspend the resulting solid in diethyl ether (200 mL) and filter to afford 31.1 g (94percent) of the crude title compound. MS/ES m/z 128.3 [M+H]+. |
94% | Stage #1: With dimethylsulfide borane complex In tetrahydrofuran for 16 h; Heating / reflux Stage #2: at 20℃; for 0.333333 h; |
Step 1. 2-Thiophene-3-yl-ethylamine hydrochloride; Slowly add borane methyl sulfide complex (30.4 mL, 304.4 mmol) to a solution of thiophen-3-yl-acetonitrile (25.0 g, 203.0 mmol) in tetrahydrofuran (450 mL). Heat the reaction at reflux for 16 h and then cool to RT. Slowly quench the reaction with methanol (50 mL) until no foaming is observed. To this mixture slowly add methanol (100 mL) which is saturated with hydrogen chloride. Stir the mixture at RT for 20 min before concentrating in vacuo. Add methanol (100 mL) to the mixture and concentrate in vacuo. Suspend the resulting solid in diethyl ether (200 mL) and filter to afford 31.1 g (94percent) of the crude title compound. MS/ES m/z 128.3 [M+H]+ |
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