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[ CAS No. 63285-84-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 63285-84-7
Chemical Structure| 63285-84-7
Chemical Structure| 63285-84-7
Structure of 63285-84-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63285-84-7 ]

CAS No. :63285-84-7 MDL No. :MFCD00178747
Formula : C10H8OS Boiling Point : -
Linear Structure Formula :- InChI Key :DXSHUWUDKNEGFS-UHFFFAOYSA-N
M.W :176.23 Pubchem ID :7018947
Synonyms :

Calculated chemistry of [ 63285-84-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.84
TPSA : 37.47 Ų

Pharmacokinetics

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) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 3.54
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 3.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.45
Solubility : 0.0624 mg/ml ; 0.000354 mol/l
Class : Soluble
Log S (Ali) : -3.59
Solubility : 0.0457 mg/ml ; 0.000259 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.92
Solubility : 0.0211 mg/ml ; 0.00012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 63285-84-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338-P405-P501 UN#:2810
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 63285-84-7 ]

* 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.

  • Downstream synthetic route of [ 63285-84-7 ]

[ 63285-84-7 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 872-31-1 ]
  • [ 108-95-2 ]
  • [ 63285-84-7 ]
YieldReaction ConditionsOperation in experiment
74% copper(I) chloride; In pyridine; mineral oil; A. 3-Phenoxythiophene Cuprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with Et2O (200 ml) and washed with 1 N NaOH (3*100 ml), 1 N HCl (2*150 ml) and 1 N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).
74% copper(I) chloride; In pyridine; mineral oil; A. 3-Phenoxythiophene Cuprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with Et2 O (200 ml) and washed with 1N NaOH (3*100 ml), 1N HCl (2*150 ml) and 1N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).
74% In pyridine; mineral oil; A. 3-Phenoxythiophene. Couprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with EtO (200 ml) and washed with 1N NaOH (3*100 ml), 1N HCl (2*150 ml) and 1N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).
31 g (29%) With copper; potassium carbonate; In chloroform; a) 3-phenoxythiophene. A mixture of 3-bromothiophene (100 g, 610 mMol), phenol (61.2 g, 650 mMol), copper bronze (5 g) and potassium carbonate (30 g, 220 mMol) was heated to 150 C. After heating for 7 days the mixture was cooled, diluted with 300 mL of chloroform and filtered. The solids were thoroughly washed with chloroform and the filtrates combined. The combined organics were washed with 10% NaOH (2*300 mL), water (300 mL), dried (MgSO4) and concentrated. The residue was factionally distilled to afford 31 g (29%) (80 C., 3 mm) of the desired ether as a clear liquid.

  • 2
  • [ 63285-84-7 ]
  • [ 124-38-9 ]
  • [ 81028-68-4 ]
  • [ 81028-69-5 ]
  • 3
  • [ 63285-84-7 ]
  • [ 124-38-9 ]
  • [ 81028-68-4 ]
  • [ 81028-70-8 ]
  • 4
  • [ 63285-84-7 ]
  • [ 166964-13-2 ]
YieldReaction ConditionsOperation in experiment
17% With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran; B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38 M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2- sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).
17% With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran; B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38 M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).
17% With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran; B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).
17% With N-chloro-succinimide; sulfur dioxide; In tetrahydrofuran; B. 3-Phenoxythiophene-2-sulfonyl chloride BuLl (2.38M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 250 C. and stirred at for 2 more hours. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).

  • 6
  • [ 63285-84-7 ]
  • N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide [ No CAS ]
  • 8
  • [ 63285-84-7 ]
  • [ 81028-71-9 ]
  • 9
  • [ 63285-84-7 ]
  • [ 132706-25-3 ]
YieldReaction ConditionsOperation in experiment
1.74 g (75%) With n-butyllithium; In water; N,N-dimethyl-formamide; b) <strong>[63285-84-7]3-phenoxythiophene</strong>-2-carboxaldehyde. To a 0 C. solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (2 g, 11.4 mMol) in ether (50 mL) was added n-butyllithium (5 mL, 12.5 mMol, 2.5M in hexanes). The reaction was stirred for 15 min and N,N-dimethylformamide (3 mL) was added. The reaction was allowed to warm to room temperature. Water (5 mL) was added cautiously while stirring. The reaction mixture was diluted with ether and washed with water (100 mL). The aqueous layer was washed with ether and the organic layer combined, washed with brine, dried (MgSO4), and concentrated. The residue was purified by flash column chromotography (SiO2, eluted with 10% ethylacetate/hexanes) to afford 1.74 g (75%) of the desired aldehyde as a clear oil. The title compound was prepared according to the method of Example 127 using <strong>[63285-84-7]3-phenoxythiophene</strong>-2-carboxaldehyde (prepared above) instead of 3-bromothiophene-2-carboxaldehyde. mp: 132-133.5 C.; NMR (300 MHz, DMSO-d6) δ 4.55 (2H, s), 6.43 (2H, bs), 6.72 (1H, d, J=6 Hz), 6.95 (2H, m), 7.06 (1H, m), 7.33 (2H, m), 7.46 (1H, d, J=6 Hz), 9.44 (1H, s); MS m/e (DCI/NH3) 282 (M+NH4)+, 265 (M+H)+.
  • 10
  • [ 63285-84-7 ]
  • [ 132706-26-4 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium; chloro-trimethyl-silane; In water; N,N-dimethyl-formamide; a 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde To a 0 C. solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (9.5 g, 53.9 mMol) in ether (200 mL) was added n-butyllithium (24 mL, 60 mMol, 2.5M in hexanes). The reaction was stirred for 15 min and trimethylsilyl chloride (6.45 g, 59.4 mMol) was added via syringe. The reaction was stirred 15 min and additional n-butyllithium (24 mL, 60 mMol, 2.5M in hexanes) was added and the reaction stirred 15 min. To the cold reaction mixture is added DMF (14 mL) and the reaction allowed to warm to room temperature over night. Water (5 mL) was added cautiously while stirring. The reaction mixture was diluted with ether and washed with water. The aqueous layer was washed with ether and the organic layer combined, washed with brine, dried (MgSO4), and concentrated. Purification by flash chromatography (SiO2, eluted with 5% ether/hexanes) afforded 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde (12.1 g, 83%) as a slightly yellow oil. The title compound was prepared as described in Example 137 except using 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde described above instead of 5-phenylthio-2-trimethylsilylthiophene-3-carboxaldehyde. mp: 120-122 C.; NMR (300 MHz, DMSO d6) δ 4.57 (2H, s), 6.46 (2H, bs), 6.78 (2H, s), 7.03 (2H, m), 7.12 (1H, m), 7.38 (2H, m), 9.49 (1H, s); MS m/e (DCI/NH3) 282 (M+NH4)+, 265 (M+H)+.
  • 11
  • [ 63285-84-7 ]
  • [ 591-50-4 ]
  • [ 1260170-07-7 ]
  • 12
  • [ 63285-84-7 ]
  • [ 41872-51-9 ]
YieldReaction ConditionsOperation in experiment
53% With palladium(II) trifluoroacetate; silver(I) acetate; In propionic acid; at 110℃; for 20.0h;Schlenk technique; Inert atmosphere;Catalytic behavior; General procedure: To a 10 mL Schlenk flask were placed 3-phenoxybenzo[b]thiophene (45.3 mg, 0.2 mmol), Pd(TFA)2 (6.6 mg, 0.02 mmol), AgOAc (66.8 mg, 0.4 mmol), and propionic acid (1.0 mL), the atmosphere was replaced by nitrogen, and the cock was closed. The mixture was magnetically stirred at 110 oC for 20 h. After cooling, the mixture was filtered through a celite pad and poured into aqueous NaHCO3, extracted with ethyl acetate, and dried over Na2SO4. Evaporation of the solvent and purification with column chromatography on silica gel using hexane/ethyl acetate (80:1, v/v) gave BTBF 2b (36.3 mg, 81%).
  • 13
  • [ 63285-84-7 ]
  • C10H5(2)HOS [ No CAS ]
  • C10H7(2)HOS [ No CAS ]
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