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Product Details of [ 825-44-5 ]

CAS No. :825-44-5 MDL No. :MFCD00052178
Formula : C8H6O2S Boiling Point : -
Linear Structure Formula :- InChI Key :FRJNKYGTHPUSJR-UHFFFAOYSA-N
M.W : 166.20 Pubchem ID :69997
Synonyms :

Calculated chemistry of [ 825-44-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.71
TPSA : 42.52 Ų

Pharmacokinetics

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) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 2.42
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 1.37
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.83
Solubility : 2.47 mg/ml ; 0.0148 mol/l
Class : Very soluble
Log S (Ali) : -1.36
Solubility : 7.3 mg/ml ; 0.0439 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.666 mg/ml ; 0.00401 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.97

Safety of [ 825-44-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 825-44-5 ]

* 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.

  • Upstream synthesis route of [ 825-44-5 ]
  • Downstream synthetic route of [ 825-44-5 ]

[ 825-44-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 825-44-5 ]
  • [ 19983-44-9 ]
YieldReaction ConditionsOperation in experiment
84% at 0℃; for 0.5 h; Reference Example 118
6-Nitro-1-benzothiophene 1,1-dioxide
Nitric acid (10 mL) was slowly added to sulfuric acid (10 mL) at 0°C, and the mixture was stirred at the same temperature for 10 min.
To this solution was slowly added 1-benzothiophene 1,1-dioxide (3.99 g) at 0°C, and the mixture was further stirred at the same temperature for 30 min.
The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate.
The extract was washed twice with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The residue was recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow solid (yield 4.26 g, 84percent).
1H-NMR (CDCl3)δ: 7.00 (1H, d, J=6.9 Hz), 7.33 (1H, dd, J=1.2, 6.9 Hz), 7.58 (1H, d, J=8.4 Hz), 8.47 (1H, dd, J=1.8, 8.4 Hz), 8.55-8.57 (1H, m).
Reference: [1] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 154-155
[2] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0292
[3] Journal of the Chemical Society, 1948, p. 1615,1617
[4] Journal of the Chemical Society, 1957, p. 826,830
[5] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 963 - 968
[6] Patent: EP1803709, 2007, A1,
  • 2
  • [ 825-44-5 ]
  • [ 7697-37-2 ]
  • [ 19983-44-9 ]
  • [ 22952-26-7 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 1615,1617
  • 3
  • [ 95-15-8 ]
  • [ 825-44-5 ]
YieldReaction ConditionsOperation in experiment
100% With tert.-butylhydroperoxide; [Mo2(O)4[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 1 h; Reflux General procedure: In a 25 mL round-bottom flask equipped with a magnetic stirring bar, a solution of sulfide (1 mmol), catalyst (6 mg, 0.008 mmol, 0.016 mmol Mo) in 1,2-dichloroethane (4 mL) was prepared. TBHP (2 mmol) was added to this solution and the reaction mixture was stirred under reflux conditions. The reaction progress was monitoredby TLC. After the reaction was completed, the isolation and purification of the products were done as described above.
99% With formic acid; dihydrogen peroxide In dichloromethane at 20℃; To a solution of benzothiophene (0501-36) (2.0 g, 15 mmol, 1.0 eq.) in dichloromethane (20 ml) was added 30percent hydrogen peroxide solution (6 ml) and formic acid (4 ml).The reaction was stirred at room temperature overnight.Add sodium bicarbonate solution (100 ml), extract with dichloromethane (100 ml × 3), and combine organic phases.Dry over anhydrous sodium sulfate, filter, and spin dry.The white solid product benzo[b]thiophene 1,1-dioxide (4.0 g, yield: 99percent) was obtained.
98% With dihydrogen peroxide In ethanol; n-heptane; water at 60℃; for 2.16667 h; General procedure: Solid sulfides were oxidized to the corresponding sulfonesby stirring a solution of the sulfide (1 mmol) and the catalyst(0.15 g) in n-heptane-ethanol (v/v, 4:2). Then a certain amountof H2O2 (30percent aq.) was added as the oxidant. The mixture wasstirred for a specified time at 60 °C, and the reaction was monitoredusing thin-layer chromatography. After completion ofthe reaction, the catalyst was separated from the reaction solutionusing an external magnet. The corresponding sulfoneproducts were separated from the reaction mixture. The solventwas evaporated to generate the crude product. The crude product was purified by column chromatography on silica gelusing hexane/ethyl acetate as the eluent (method b).
94% With dihydrogen peroxide In water at 20℃; for 0.5 h; General procedure: To a mixture of sulfide (1 mmol) and catalyst (0.04 g), H2O2 30percent(v/v) (0.28 g, 2.5 equiv.) was added and stirred at room temperature for a specified time. After completion of the reaction, as indicated on thin-layer chromatography (TLC), ethyl acetate (20 mL) was added and the mixture was centrifuged to separate the catalyst. The filtrate was washed with brine and dried over anhydrous Na2SO4. Purification of the combined organics by preparative TLC (hexane-ethyl acetate, 10:1) provided pure products. The recycled catalyst was washed with ethyl acetate and acetone. After being dried at 60 °C, it can be reused without further purification. All of the products were known and identified by comparison of their melting points and spectral data with those reported in the literature 2.4.
90% With dihydrogen peroxide In ethanol; hexane; water at 80℃; for 1.08333 h; General procedure: A mixture of 0.03 g of the catalyst and 30percent H2O2 (10 mmol)aq. was added to a solution of the sulfide (1 mmol) in a mixedsolvent of EtOH and hexane (1:1; 2 mL), and the resulting mixture was stirred at 80 °C. The reaction mixture was cooled toroom temperature and the catalyst was separated using anexternal magnetic field. The corresponding sulfones were extractedwith EtOH from the reaction mixture (Method c, Table2, entries 8–11).
87% With dihydrogen peroxide In octane; acetonitrile at 20℃; for 0.25 h; Sonication; Green chemistry General procedure: The UAOD generally carry out in biphasic system that consistsof a polar solvent and model fuel. The UAOD studies wereperformed with model oil, with refractory sulfur compoundscommonly found in fuels (BT, DBT or 4,6-DMDBT), was preparedby dissolving in n-octane (500 mg.L1 for each compound). TheUAOD reactions were carried out in a biphasic medium that formedby the model fuel and different polar solvent such as water,acetonitrile (MeCN), isopropanol and dimethylformamide (DMF).In a generic experiment, 15 mg of PTATMU-17-NH2 (containing 20 wtpercent of PTA) was placed in the vessel then a mixture of MeCN (5 mL) and model fuel (5 mL, 2.5 mgr of DBT) was added to it andthe catalytic process was started with addition of H2O2 30percent(1:1 oxidant/S-contain compound molar ratio (O/S)) as oxidant inreaction medium. In next step, the resulting mixture was exposedultrasound waves for 5 min in an ultrasonic bath at ambient temperature(100W and 37 kHz). In order to stop the reaction, theflask was put into an ice bath. Supernatant layer that is model oilwas decanted, then catalyst was separated from the lower layerwith centrifuge. The reaction progress was quantified periodicallyby GC and tetradecane as a standard. PTATMU-17-NH2 could berecycled by centrifuge the catalyst after each UAOD cycle, then,soaking MeCN at room temperature. The UAOD system was optimizedusing PTATMU-17-NH2 as catalyst (5–30 mg), differentextraction solvent and various O/S molar ratio (1:1, 2:1, 3:1) indifferent time (5–20 min) under various powers of ultrasonicirradiation (50–150 W, 37 kHz) at ambient temperature.
85% With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane In tetrahydrofuran at 20℃; for 2.33333 h; Green chemistry General procedure: To a stirred solution of sulfde (1 mmol) and THF (4 mL),THPDPE (1 up to 5.5 mmol (0.310 up to 1.70 g) dependingon the substrates and products) was added and the mixture wasstirred at room temperature for an appropriate time. After completion of the reaction, as monitored by TLC, a saturated aqueous solution of Na2SO3 (2 mL of 1 M solution) was added toquench the excessive oxidant that was remained in the mixture.Water (10 mL) was added to the mixture and extracted usingchloroform (3 × 5 mL) and dried over anhydrous MgSO4. Afterevaporation of solvent under reduced pressure chromatographyon silica gel was used to give pure products.
84% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16 h; m-Chloroperbenzoic acid (77percent, 6.35 g, 27.9 mmol) was added portion wise to a solution of benzo[£>]thiophene (1 .50 g, 1 1 .1 mmol) in anhydrous dichloromethane (100 ml_) at room temperature with vigorous stirring, the resulting reaction mixture was stirred for 16 h at the same temperature. A saturated aqueous NaHC03 solution (250 mL) was added and aqueous layer was extracted with dichloromethane (2 x 100 m L), organic layer was separated, combined organic layers dried (MgS04) and concentrated in vacuo. Crystallization from ethanol afforded benzo[b]thiophene 1 , 1 -dioxide (1 .56 g, 84percent) as an off-white solid. 1 H NMR (600 MHz, CDCI3): δ = 7.73 (d, J = 6 Hz, 1 H), 7.58-7.53 (m, 2H), 7.38 (d, J = 12 Hz, 1 H), 7.23 (d, J= 6 Hz, 1 H), 6.73 (d, J = 6 Hz, 1 H). LCMS (m/z): 167 [M +H] +
81% With tert.-butylhydroperoxide In hexane; toluene at 40℃; for 6 h; 0.15 g (0.0011 mol) benzothiophene (BT) was placed in a 25 mL round bottom flask containing 10 mL mixture of toluene/hexane (1:4) and 0.015 g (0.0135 mmol) of oxidation catalyst. The mixture was heated to 40 °C with continuous stirring at 500 rpm in an oil bath. An oxidant-to-substrate ratio of 6.8 was then added to the mixture. The oxidation reaction was allowed to proceed for 6 h under continuous stirring after the addition of tert-butylhydroperoxide. A white precipitate of benzothiophene sulfone (BTO2) observed was collected through filtration and washed with hexane to remove unreacted benzothiophene. Yield = 81percent. 1H NMR (δ, ppm in DMSO) δ 7.83 (d, J = 7.2, 1H), 7.69 (t, J = 7.4, 1H), 7.62 (t, J = 9.1, 3H), 7.34 (d, J = 6.8, 1H). Anal. Calcd(found) for C8H6O2S (percent): C, 57.81(57.49); H, 3.64(3.89); S 19.29(19.02).
74% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 35℃; for 2 h; Reference Example 117
1-Benzothiophene 1,1-dioxide
To a solution (120 mL) of 1-benzothiophene (11.2 g) in tetrahydrofuran was added m-chloroperbenzoic acid (70percent containing, 43.1 g) at 0°C and the mixture was stirred at the same temperature for 1 hr, further stirred at room temperature for 1 hr.
An aqueous sodium thiosulfate solution (50 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
The extract was washed with 1 mol/L aqueous sodium hydroxide solution, saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The residue was recrystallized from ethyl acetate to give the title compound as a white solid (yield 10.3 g, 74percent).
1H-NMR (CDCl3)δ: 6.72 (1H, d, J=7.0 Hz), 7.20-7.24 (1H, m), 7.34-7.38 (1H, m), 7.52-7.60 (2H, m), 7.70-7.74 (1H, m).

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  • 4
  • [ 95-15-8 ]
  • [ 825-44-5 ]
  • [ 51500-42-6 ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butylhydroperoxide; [Mo2(O)4[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 0.5 h; Reflux General procedure: In a 25 mL round-bottom flask equipped with a magnetic stirring bar, a solution of sulfide (1 mmol), catalyst (6 mg, 0.008 mmol, 0.016 mmol Mo) in 1,2-dichloroethane (4 mL) was prepared. TBHP (2 mmol) was added to this solution and the reaction mixture was stirred under reflux conditions. The reaction progress was monitoredby TLC. After the reaction was completed, the isolation and purification of the products were done as described above.
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[4] RSC Advances, 2014, vol. 4, # 102, p. 58800 - 58804
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[7] ChemCatChem, 2017, vol. 9, # 19, p. 3714 - 3724
[8] Dalton Transactions, 2018, vol. 47, # 29, p. 9677 - 9684
  • 5
  • [ 51500-42-6 ]
  • [ 825-44-5 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 9, p. 3271 - 3278
[2] Asian Journal of Chemistry, 2017, vol. 29, # 8, p. 1723 - 1727
  • 6
  • [ 95-15-8 ]
  • [ 825-44-5 ]
Reference: [1] Patent: EP1803709, 2007, A1,
  • 7
  • [ 95-15-8 ]
  • [ 825-44-5 ]
  • [ 121823-04-9 ]
  • [ 239-35-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 4, p. 782 - 790
  • 8
  • [ 7722-84-1 ]
  • [ 64-19-7 ]
  • [ 95-15-8 ]
  • [ 825-44-5 ]
  • [ 20841-53-6 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 4678,4681
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