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* Storage: {[proInfo.prStorage]}
CAS No. : | 34722-01-5 | MDL No. : | MFCD00143179 |
Formula : | C8H12S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KPOCSQCZXMATFR-UHFFFAOYSA-N |
M.W : | 140.25 | Pubchem ID : | 566339 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.71 |
TPSA : | 28.24 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) : | -4.39 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 3.9 |
Log Po/w (WLOGP) : | 3.09 |
Log Po/w (MLOGP) : | 2.6 |
Log Po/w (SILICOS-IT) : | 3.92 |
Consensus Log Po/w : | 3.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.38 |
Solubility : | 0.0585 mg/ml ; 0.000417 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.19 |
Solubility : | 0.00903 mg/ml ; 0.0000644 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.0807 mg/ml ; 0.000575 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P403+P235 | UN#: | 1993 |
Hazard Statements: | H225 | Packing Group: | Ⅲ |
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 |
---|---|---|
90% | 3-Butylthiophene (1.40 g) was added to a dry THF solvent in a 3-bulb flask. Then, under argon gas atmosphere, the temperature was lowered to -78 C. After adding 2.5 M n-BuLi/hexane (~4 mL) dropwise over 1.5 hours, the resulting solution was activated by stirring at -78 C for about 1 hour. At the same temperature, a solution of bromine (1.68 g) and THF (5 mL) was slowly added for about 15 minutes. The mixture was stirred for 20 minutes and a few drops of an aqueous methanolic solution of sodium thiosulfate were added at -78 C . The reaction mixture was warmed to room temperature by removing the cooling bath, poured into ice cold water and extracted with diethyl ether. The organic layer was washed successively with 3% Na2S203 (30 mL) , water and 10% NaCl (50 mL) , and was dried over anhydrous Na2SC> . The solvent was removed under reduced pressure and the resulting light yellow oil was purified by flash column chromatography on neutralized silica gel with hexane . Apale-yellow liquid substance was obtained. The yield was 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | 2-(4-Butyl-thiophen-2-yl)-ri ,3,21dioxaborinane: To a solution of diisopropylamine (21.6 ml, 154.0 mmol) in 200 ml of anhydrous diethyl ether was added 2.5 M n-BuLi in hexane(49.3 ml, 123.3 mmol) at room temperature. After stirring at room temperature for 30 min, the resulting lithium di-isopropylamide (LDA) solution was cooled to -760C. A solution of <strong>[34722-01-5]3-butylthiophene</strong> (18.0 g, 123.3 mmol) in 100 ml of ether was cooled to EPO <DP n="38"/>-76 0C and added to the above LDA solution. The temperature was allowed to rise slowly to -AQ 0C, whereupon it was stirred for 1 h. The solution was then recooled to -760C and trimethylborate (20.6 ml, 185.0 mmol) was added slowly. The mixture was allowed to warm to room temperature and stirred for 2 h. After quenching with 10% HCI (180 ml) the* organic layer was separated and the aqueous layer was extracted with ether (2x). The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was added to 1 ,3-propanediol (8.9 ml, 123.3 mmol) and refluxed for 2 h. The mixture was then placed directly on a silica column and eluted first with hexane, then chloroform to give the product, 8.46 g, 31 %. 1H NMR (CDC/3-d3, 500 MHz): delta 7.36 ppm (s, 1 H), 7.12 ppm (s, 1 H), 4.14-4.12 ppm (t, 4 H, J = 8.6 Hz), 2.60-2.63 ppm (t, 2 H1 J = 8.6 Hz), 2.04 ppm (m, 2 H), 1.35 ppm (m, 2 H), 1.32 ppm (m, 2 H), 0.89 ppm (t, 3 H, J = 7.5 Hz); 13C-NMR (CDCI3, 500 MHz): delta 144.4, 136.8, 126.5 126.4, 62.1 , 32.85, 29.73, 27.46, 22.45,13.90 ppm. El, MS m/z (%): 224 (100, M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With N,N,N,N,-tetramethylethylenediamine; di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium; zinc; In water; at 20℃; for 24h;Inert atmosphere; | General procedure: In a 5 mL round-bottom flask under argon containing zinc powder (197 mg, 3 mmol) and PdCl2(Amphos)2 (7 mg, 0.01 mmol) was added 2% PTS solution in water (1.5 mL). N,N,N',N'-Tetramethylethylenediamine (TMEDA, 232 mg, 2 mmol) was added at rt followed by the addition of the alkyl halide (2 mmol) and the heteroaromatic halide (0.5 mmol). The flask was stirred vigorously at rt for the indicated time. The product was extracted with EtOAc.11 Silica gel (1 g) was added to the combined organic phase and solvents were removed under vacuum. The resulting dry, crude silica was introduced on top of a silica gel chromatography column to purify the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride; In dichloromethane; at 20℃; for 24h; | A solution of 3-n-Butilthiophene (50 mg, 0.33 mmol), acetyl chloride (50 mul, 0.66 mmol) and anhydrous CH2Cl2 (1 ml) was added dropwise with stirring to a mixture of anhydrous aluminium trichloride (67 mg, 0.5 mmol) in anhydrous CH2Cl2 (2 ml). The solution was stirred at room temperature for 24 h until completeness. The resulting mixture was then washed with H2O (3 * 2 ml). Organic phase was evaporated in vacuum and lyophilized. The obtained product, without further purification, was brominated with NBS following method A to furnish 2-bromo-1-(4-butylthiophen-2-yl) ethanone. The bromoketone (78 mg, 0.3 mmol) was then conjugated with 1-(3-(methylthio) phenyl) thiourea a (60 mg, 0.3 mmol) in refluxing ethanol (1 ml). After 7 h the reaction was complete and the product was purified by preparative HPLC and the peak of interest was concentrated to obtain the title compound. (79 mg,67%) 1H NMR (300 MHz, CDCl3): delta 7.53 (d, J = 1.5 Hz,1H), 7.44 (t, J = 2.0 Hz, 1H), 7.26 (t, J = 7.7 Hz, 1H), 7.10 (ddd, J = 8.0, 2.2, 0.9 Hz, 1H), 7.08 (d, J = 1.5 Hz, 1H), 6.97 (ddd, J = 7.8, 1.8, 0.9 Hz, 1H), 6.70 (s, 1H),2.65 (t, J = 7.1, 2H), 2.52 (s, 3H), 1.61 (m, J = 7.1 Hz, 2H), 1.31 (m, J = 7.1 Hz, 2H), 0.90 (t, J = 8 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 159.1, 145, 142.5, 140.4, 138.3, 137.2, 128.3, 125.5, 121.7, 119.3, 114.2, 113.2, 105.6, 34.1, 30.9, 22.3, 14.7,14.1. ESI-MS m/z = 361.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Reagents <strong>[34722-01-5]3-butylthiophene</strong> (1a) and diisopropylamine were dried by passage through an alumina column then degassed by bubbling dinitrogen through the reagents for 30 minutes. A solution of n-BuLi (100 mL, 2.5 M, 250 mmol) was added drop wise over 1 hour to a solution of <strong>[34722-01-5]3-butylthiophene</strong> (31.5 g, 225 mmol) and diisopropylamine (34.15 g, 337.5 mmol) in 250 mL of THF at -78 C. The reaction mixture was allowed to warm to rt, then cooled to -78 C when chlorotrimethylsilane (28.93 g, 266 mmol) was slowlyadded. The reaction mixture was allowed to warm to rt and stirred for 1 hour. The reaction was quenched by addition of250 mL of water. The THF was removed under rotary evaporation and was followed by the addition of 200 mL of diethyl ether. The organic phases were separated, washedwith water (2 × 100 mL) then dried over MgSO4. The slurry was filtered to remove the MgSO4, the solvent removed under vacuum and the crude product distilled at 90 C at 700 mTorr to yield the product as a clear oil (36.1 g, 170 mmol, 77%). IR (neat) nu= 2956, 2929, 2859, 1248, 1006, 820 cm-1. 1H NMR (600 MHz, CDCl3) delta = 7.17 (s, 1 H), 7.08 (s, 1 H), 2.65 (t, J = 7.8 Hz, 2 H), 1.68-1.59 (m, 2 H), 1.40-1.37 (m, 2 H), 0.95 (t, J = 6.7 Hz, 3 H), 0.33 (s, 9 H). 13C NMR (100 MHz, CDCl3) delta = 144.6, 140.0, 135.5, 125.3, 32.9, 29.7, 22.5, 13.9, 0.01. MS (ESI) m/z [M+H]+= 212.1494. Elemental analysis calculated for C11H20SSi: Calculated: C, 62.19; H, 9.49; S, 15.09; Si, 13.22; found: C, 62.12; H, 9.64; S, 14.92 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.6 g | A 1 L, three-neck flask was charged with DMF (208 g, 2.852 mol). Under nitrogen gas (N2), POC13 (60 g, 392 mmol) was added slowly while the temperature was kept below 10 C using an ice bath. After the addition was complete, the ice bath was removed and the reaction mixture was allowed to warm to room temperature and stirred for 10 minutes. 3 -Butylthiophene (50 g, 357 mmol) was added. Thereaction mixture was stirred at room temperature for 10 minutes and then heated to 70 C and stirred for additional 4.5 hours. The resulting reaction mixture was added to a NaOH solution (5%, 400 mL) and extracted with methyl-tert-butyl ether (600 mL). The organic layer was separated, washed with brine and dried over MgSO4. Further purification of the crude with distillation (98 C /2.86 mm Hg) afforded 3-butyl-2-formylthiophene (45.6 g).?H NMR (CDC13, 400-MHz): 10.02-10.07 ppm (m, 1H), 7.64 ppm (d, J=5.0 Hz, 1H), 7.01 ppm (d, J5.0 Hz, 1H), 2.97 ppm (t, J7.9 Hz, 2H), 1.57-1.77 ppm (m, 2H), 1.28-1.47 ppm (m, 2H), 0.94 ppm (t, J=7.3 Hz, 3H) |
Tags: 34722-01-5 synthesis path| 34722-01-5 SDS| 34722-01-5 COA| 34722-01-5 purity| 34722-01-5 application| 34722-01-5 NMR| 34722-01-5 COA| 34722-01-5 structure
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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Health hazards | |
Code | Phrase |
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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