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CAS No. : | 7372-88-5 | MDL No. : | MFCD00216258 |
Formula : | C13H10S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NICUQYHIOMMFGV-UHFFFAOYSA-N |
M.W : | 198.28 | Pubchem ID : | 30364 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 13 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.3 |
TPSA : | 28.24 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.14 cm/s |
Log Po/w (iLOGP) : | 2.65 |
Log Po/w (XLOGP3) : | 4.74 |
Log Po/w (WLOGP) : | 4.36 |
Log Po/w (MLOGP) : | 4.17 |
Log Po/w (SILICOS-IT) : | 5.2 |
Consensus Log Po/w : | 4.22 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.74 |
Solubility : | 0.00359 mg/ml ; 0.0000181 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.06 |
Solubility : | 0.00172 mg/ml ; 0.00000865 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.41 |
Solubility : | 0.000773 mg/ml ; 0.0000039 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.76 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P301+P312-P330-P403-P501 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
With n-butyllithium; diethyl ether | ||
With n-butyllithium 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h; Yield given. Multistep reaction; | ||
With n-butyllithium 1) ether, THF, 1 h, reflux, 2) 1 h, reflux; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dihydrogen peroxide In ethanol at 20℃; for 0.75h; Irradiation; | |
77.9% | With Cumene hydroperoxide; molybdenum(VI) oxide In octane at 100℃; for 5h; | 2 Example 2[46] The reaction for preparation of 4-MDBT sulfone is shown below:4-MDBT 4-MDBT sulfone[47] 2g of 4-MDBT (10.09mmol) was dissolved in 80 ml of octane in a 250ml round- bottomed flask. lOOmg of M0O3 and 10ml of cumene hydroperoxide (54.14mmol) were added. The mixture was heated to 100°C for 5h with magnetic stirring. After cooling down to room temperature, large amount of white solid was filtered and washed with hexane. The white solid was dried in air and then dissolved in CH2C12. The insoluble precipitation was filtered and washed with CH2C12. CH2C12 was evaporated to dryness to give 1.81g(77.9%) of white crystalline solid. GC data (FIG. 3, middle) indicated that there is only one species. GC-MS result confirmed that it is 4-MDBT sulfone.[48] 4-MDBT sulfone Ci3Hi0O2S, MW: 230.28. GC-MS: 230(100%), 201(29.5%), 187(25.5%), 181(36.1%), 165(21.3%), 152(20.5%), 139(20.1%), 136(29.3%), 115(20.1%), 63(19.1%). |
75% | With borax; dihydrogen peroxide; sodium hydroxide In methanol; water at 20℃; for 24h; chemoselective reaction; |
With dihydrogen peroxide; acetic acid | ||
With dihydrogen peroxide; acetic acid for 0.166667h; Heating; | ||
With formic acid; dihydrogen peroxide; oxygen at 60℃; for 1h; | ||
With [Cr3F(H2O)2O(1,4-benzenedicarboxylate)3]; oxygen In dodecane at 120℃; | ||
With dihydrogen peroxide for 0.5h; | 2.4. Catalytic activity tests General procedure: The activity tests were carried out in a condenser-equippedglass-batch reactor with a mechanical stirrer. This system wasimmersed in a recirculating bath with a thermostat control to main-tain a constant temperature of 60C. The model solution (50 cm3)and the catalyst (100 mg) were added to the reactor and then stirredvigorously (750 rpm) to avoid external mass transfer problems andto ensure kinetic regime as mentioned in [44]. H2O2(30%, v/v)or TBHP (70%, v/v) were used as oxidant agents. When the reac-tion temperature was reached, the oxidant agent was introducedto the reactor with a molar ratio of oxygen:sulfur = 6:1 (O/S = 6),to maintain an excess of three times relative to the stequiometric amount (O/Sstequiometric= 2). Small samples of the reaction mix-ture were withdrawn at 15, 30, 60 and 90 min and injected (autosampler) to a gas chromatograph with flame ionization detector(GC-FID) after cooling at room temperature to follow the reactionprogress. GC-FID analyses were performed with an HP5890 SeriesII Gas Chromatograph with a PONA capillary column (Methyl Sil-icone Gum, 50 m × 0.2 mm × 0.5 m film thickness). Reactant andproduct identifications were achieved with GC-PFPD (Varian CP-3800) and GC-MS (HP5890 Series II with MS detector). The oxidantagent was added to the reactor gradually in small doses to reducethe thermal decomposition, according to previous results [28-30].The oxidant agent amount in the system was measured during thecatalytic reaction to maintain the O/S ratio constant. Permangano-metric titration and GC-FID were used to follow the decompositionof TBHP, and standard iodometric titration to follow the decompo-sition of H2O2. | |
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 120℃; for 4h; | ||
With K6LiH6[Ce4(H2O)14(2,3-pyrazinedicarboxylato)(2,3-pyrazinedicarboxylic acid)As3W29O103]*22H2O; dihydrogen peroxide In toluene; acetonitrile at 25℃; for 1h; | ||
With C6O61P2Re2W17(10-)*6C4H12N(1+)*4H(1+); dihydrogen peroxide In acetonitrile at 60℃; for 1.5h; | ||
With dihydrogen peroxide In octane at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium at 300℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorous (V) sulfide at 400℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 18h; | |
83% | With triethylsilane; potassium <i>tert</i>-butylate In 1,3,5-trimethyl-benzene at 165℃; for 60h; Inert atmosphere; Glovebox; | 6.8 Experiments with C-N and C-S Heteroaryl Compounds at Elevated Temperatures In the case of compounds comprising C-S compounds, the methods appear to generally result in complete desulfurization of the molecules, at least under the aggressive conditions of these experiments, reflecting the higher reactivity of these types of substrates (but compare with Examples 6.9.34 to 38). This difference in reactivities may reflect the differences in bond energies between the C-O, C-N, and C-S bonds (compare C-X bond dissociation energies in phenol (111), aniline (104), and thiophenol (85, all in kcal/mol). Of particular interest is the desulfurization of even hindered dibenzothiophenes under relatively mild conditions. In none of these conversions were single C-S products detected: |
63 % Chromat. | With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol for 1h; Ambient temperature; |
> 90 %Spectr. | With sodium; 1,1,2,2-tetraphenylethylene In tetrahydrofuran at 20℃; for 14.5h; Inert atmosphere; regioselective reaction; | 4.3. Reductive desulfurization procedure General procedure: Deep red suspensions of Na, Li or Na and Li metals in the presence of a catalytic amount of TPE (Na/TPE, Li/TPE or Na/Li/TPE; for the relative molar ratios, see Table 1) were prepared by vigorously stirring the freshly cut metal in dry THF (10 mL) during 1 h at rt. To this mixture, a solution of the appropriate dibenzothiophene, 1, (2 mmol) dissolved in dry THF (5 mL) was added dropwise within 30 min. The reaction mixture was vigorously stirred at rt during 14 h, after which time it was quenched by slow dropwise addition of H2O (15 mL). The organic solvent was evaporated in vacuo and the resulting mixture was extracted with Et2O or AcOEt (3×10 mL) and the organic phases were collected, washed with H2O (10 mL), brine (10 mL), and dried (Na2SO4). After evaporation of the solvent, the resulting mixtures were analyzed by GC/MS, and the reaction products 2a,26 2b,26 2c,27 2d28 and 2e29 were characterized by 1H, 13C NMR and IR spectroscopies, and by comparison with literature data. |
With dihydrogen peroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In octane; water at 70℃; for 0.166667h; | 2.8. Extractive and catalytic oxidative desulfurization processes (ECODS) General procedure: The ECODS studies were performed using a model diesel containingthe most refractory sulfur-compounds present in real diesel,namely: 1-benzothiophene (1-BT), dibenzothiophene (DBT),4-methyldibenzothiophene (4-MDBT) and 4,6- dimethyldibenzothiophene(4,6-DMDBT). All the experiments were carried outunder air (atmospheric pressure) in a closed borosilicate 5 mL reactionvessel, equipped with a magnetic stirrer and immersed in athermostatically controlled liquid paraffin bath at 70 °C. The catalyticoxidative step was performed in the presence of a polarextraction solvent, immiscible with the model diesel phase withequal volume of model diesel and extraction solvent. The ionic liquid(IL), 1butyl3methylimidazolium hexafluorophosphate(BMIMPF6) and acetonitrile (MeCN) were used as extraction solvents.These solvents acted as extraction solvents of sulfur compoundsand also as an oxidative reaction medium. The oxidationof the sulfur compounds only occurred in the presence of a catalystand an oxidant, where H2O2 (aq. 30%) was used. [BPy]3[PMo12O40]and [BMIM]3[PMo12O40] dissolved in MeCN, but showed to beinsoluble in ionic liquid solvent. In all ECODS systems 3 lmol ofeach compound was used. The heterogeneous catalyst PMo12O40(at)PPy-MSN was also studied, using 120 mg that contains 3 lmol of[PMo12O40]3- active center. In a typical experiment, 0.75 mL ofmodel diesel (containing a total sulfur concentration of2350 ppm in n-octane) and 0.75 mL of [BMIM][PF6] were addedto the catalyst. An initial extraction of sulfur compounds frommodel diesel to the IL phase occurred by only stirring the bothimmiscible phase for 10 min at 70 °C. The catalytic step of the processis then initiated by the addition of H2O2 (75 lL, 0.64 mmol).The sulfur content in the model diesel phase was periodicallyquantified by GC analysis using tetradecane as standard. Usingthe heterogeneous catalyst, recycle experiments were performedby adding a new portions of model diesel, oxidant and [BMIM][PF6] extraction solvent, at the end of each ECODS cycle. The solidcatalyst was not washed between cycles. After three cycles, thesolid was isolated from the ECODS process, followed by washingand dry to be characterized after catalytic use. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With lithium aluminium tetrahydride In diethyl ether for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 650℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 900℃; for 2.33333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: dibenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: methyl iodide | |
With n-butyllithium 1.) THF, hexane, reflux, 1,5 h, 2.) THF, reflux, RT, one night; Yield given. Multistep reaction; | ||
With n-butyllithium 1.) THF, hexane, from -78 deg C to RT, 5 h, 2.) THF, hexane, from -78 deg C to RT, 12 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 32% 3: 2.4% 4: 3% | at 450℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 400℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dioxofluoro(bis-dimethylpyrazole) vanadium(V); dihydrogen peroxide In water; acetonitrile at 0 - 20℃; for 8h; Cooling with ice; | Typical procedure for the oxidation of methyl phenyl sulfide General procedure: methyl phenyl sulfide (0.248 g, 2 mmol) in acetonitrile (2 ml) solvent was reacted with VO2F(dmpz)2 (0.0059 g, 0.02 mmol) and H2O2 (30% aqueous solution, 25 μL, 2.2 mmol) under stirring at ice bath temperature for 5 h and monitored by TLC. On completion of the reaction, acetonitrile was removed under reduced pressure and 1 ml of water was added. The product was extracted with ethyl acetate, dried over anhydrous MgSO4, and evaporated to dryness, while the aqueous layer was retained for recovery of the catalyst. In order to remove any traces of VO2F(dmpz)2, the product was transferred to silica gel (60-120 mesh) column and eluted with ethyl acetate: hexane (1:7). The aqueous layer is concentrated and reused. |
75% | With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid In hexane; dichloromethane at -30℃; Inert atmosphere; | |
65% | With nitric acid In acetonitrile at 20℃; for 90h; chemoselective reaction; |
14% | With zinc(II) chloride; 2-isopropyl-3-(pyridin-2-yl)oxaziridine In chloroform for 1h; | |
With TBA4H2[BW11Mn(H2O)O39]*H2O; dihydrogen peroxide In water; acetonitrile at 22 - 24℃; Darkness; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-methyldibenzothiophene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Stage #2: sodium thiomethoxide In N,N-dimethyl-formamide at 20 - 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h 2: 71 percent / 30percent H2O2, KOH / various solvent(s) / 0.17 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h 2: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h | ||
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h 2: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h 2: 1) BuLi / 1) THF, Et2O, hexane, reflux, 1 h, 2) reflux, 1 h 3: 71 percent / 30percent H2O2, KOH / various solvent(s) / 0.17 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h 2: multistep reaction, synthesis of 4,6-disubstituted dibenzothiophenes |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h 2: 1.) n-butyllithium, 2.) p-toluenesulfonyl chloride / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temperature, 5 h, 2.) -78 deg C to room temperature, then 10-15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aluminium chloride; sulfur 2: butyl lithium; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In nitromethane-d3 byproducts: thiophene; placing of CpRu(CO)2(thiophene)(1+) and equimolar amt. of 4-methyldibenzothiophene in a NMR tube; dissolving in CD3NO2; freezing in liq. N2; degassing, thawing, sealing under Ar at room temp.; monitoring by NMR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In nitromethane-d3 byproducts: dibenzothiophene; placing of CpRu(CO)2(dibenzothiophene)(BF4) and equimolar amt. of 4-methyldibenzothiophene in a NMR tube; dissolving in CD3NO2; freezing in liq.N2; degassing, thawing, sealing under Ar at room temp.; monitoring by NMR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | In hexane N2-atmosphere; stirring (4 h), filtering, Ni-complex addn., pptn. on stirring (room temp., 15.5 h); filtration, washing (hexanes), drying (vac.); elem. anal.; | |
26% | In hexane excess of ligand, room temp., 19 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 18% 3: 36% | In tetrahydrofuran N2-atmosphere; 22°C; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane byproducts: AgCl; Ru complex, ligand and AgBF4 were reacted in CH2Cl2 at room temp. for 30min; filtered; Et2O added; isolated; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In Cyclohexane-d12 N2-atmosphere; 63°C (57 h); evapn., extg. (hexanes); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane-d2 byproducts: dibenxothiophene; Ru complex, ligand and triphenylmethane were dissolved in CD2Cl2 in NMR tube; after 3 freeze-pump-thaw cycles tube was sealed under Ar and thermostated at 25°C; NMR monitoring; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In nitromethane-d3 byproducts: 4,6-dimethyldibenzothiophene; placing of CpRu(CO)2(4,6-dimethyldibenzothiophene)(BF4) and equimolar amt. of 4-methyldibenzothiophene in a NMR tube; dissolving in CD3NO2; freezing in liq. N2; degassing, thawing, sealing under Ar at room temp.; monitoring by NMR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane byproducts: AgCl; (Ar); using Schlenk techniques; addn. of AgBF4 to soln. of CpRu(CO)2Cl and 4-methyldibenzothiophene (excess) in CH2Cl2; stirring at room temp. for 30 min; pptn., filtration, transferring of soln. by cannula into flask containing Et2O in ice water bath; pptn., washing with CH3NO2, also transferring of soln. by cannula into Et2O, pptn., filtration, washing with Et2O; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tert.-butyl lithium In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dichloro-ethane for 2h; Photolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With tetrakis(actonitrile)copper(I) hexafluorophosphate In acetonitrile at 0℃; for 1.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 45% 2: 58% | With borax; dihydrogen peroxide; sodium hydroxide In methanol; water at 20℃; for 24h; chemoselective reaction; | |
1: 5% 2: 50% | With dihydrogen peroxide In water for 2h; | |
With dihydrogen peroxide In methanol at 20℃; for 24h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 39% 2: 10% | at 650℃; Flash vacuum pyrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In toluene (N2); soln. of Rh complex and dibenzothiophene (3 equiv.) in toluene washeated in NMR tube at 135°C for 6.5 d; NMR monitoring; evapd. (vac.); dissolved in pentane; chromd. (silica, pentane, THF/pentane, 20/80); evapd.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene-d6 (N2); soln. of Rh complex and dibenzothiophene (10 equiv.) in C6D6 was heated in NMR tube at 100°C for 1 wk; NMR monitoring; evapd. (vac.); extd. (hexane); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hexane 2: tetrahydrofuran | ||
Multi-step reaction with 2 steps 1: hexane 2: benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With palladium(II) trifluoroacetate; silver(I) acetate; potassium carbonate at 130℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver tetrafluoroborate / 1,2-dichloro-ethane / 25 °C / Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 35 °C / Inert atmosphere; Schlenk technique | ||
Multi-step reaction with 2 steps 1: silver tetrafluoroborate / 1,2-dichloro-ethane / 25 °C / Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 35 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver tetrafluoroborate / 1,2-dichloro-ethane / 25 °C / Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 35 °C / Inert atmosphere; Schlenk technique 3: silver hexafluoroantimonate / 1,2-dichloro-ethane / 12 h / 65 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: silver tetrafluoroborate / 1,2-dichloro-ethane / 25 °C / Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 35 °C / Inert atmosphere; Schlenk technique 3: silver hexafluoroantimonate / 1,2-dichloro-ethane / 12 h / 65 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In toluene at 24.84℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11 %Spectr. | In benzene-d6 Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; at 430℃;Gas phase; Flow reactor;Catalytic behavior; Activation energy; | General procedure: The catalyst was tested in a reaction of the oxidationof the sulfur-containing molecules of thiophene, DBT, and 4,6-DMDBT dissolved in toluene (0.1 wt % in terms of sulfur) with oxygen. The experiments were carried out in a flow reactor placed in a furnace with a fluidized bed of quartz sand for uniform temperature distribution; the catalyst sample weight was 2 g (partticle size of 0.5-1.0 mm). The molar ratio was O2/S =120, the gas hourly space velocity (GHSV) was 3000 h-1; the weight hourly space velocity (WHSV) of fuel was 6 h-1; and the temperature range was 245-430C. The temperature in the catalyst bed was measured with a chromel-alumel thermocouple with an accuracy of 0.5%. Model fuel was supplied to the reactor from bottom to top. A mixture of oxygen (20.8 vol %) with helium and toluene were separately supplied to the catalyst bed for preventing the gas-phase combustion of toluene out of this bed. The liquid reaction products were collected in a sample receptacle by their cooling in a reflux condenser at 5C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 7.5h; Inert atmosphere; | General procedure: To a stirred solution of 9he, 9hh or 9hi (200 mmol) in dried THF (200 mL) held at -78 °C in N2atmosphere was added dropwise 1.6 M n-BuLi in n-hexane (125 mL, 200 mmol) via syringe, and theresulting solution was stirred at -78 °C for 1 h ( for 9he and 9hh) or returned to room temperaturefor 5 h (for 9hi) before dropwise addition of dried DMF (21.93 g, 300 mmol) via syringe. Thereafterthe reaction mixture was stirred at -78 °C for 0.5 h and at room temperature for another 1 h. Thereaction mixture was poured into ice-water (600 mL) while stirring and the resulting mixture wasextracted with CH2Cl2 (300 mL × 3). The combined extracts were washed with 5% brine (500 mL),dried (Na2SO4) and evaporated on a rotary evaporator to give a residue, which was purified bycolumn chromatography to afford the pure product 10he, 10hh or 10hi. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 7.5 h / -78 - 20 °C / Inert atmosphere 2: potassium carbonate; hydroxylamine hydrochloride / water; ethanol / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With dichloro bis(acetonitrile) palladium(II); cesium pivalate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl acetamide at 140℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; | |
88% | With dichloro bis(acetonitrile) palladium(II); cesium pivalate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl acetamide at 140℃; for 24h; Inert atmosphere; Schlenk technique; | 11 Example 11 In a dry Schlenk reaction tube, add dichlorodiacetonitrile palladium (0.005mmL), bis(2-diphenylphosphine) phenyl ether (0.010mmol),Cesium pivalate (1 mmol) and o-methylthiophenol (0.2 mmol) were replaced three times in a pure nitrogen atmosphere.Then, anhydrous N,N-dimethylacetamide (2.0 mL) and o-bromoiodobenzene (0.25 mmol) were added in sequence, and the reaction was stopped after 24 hours at 140 °C. After cooling to room temperature, the system was quenched with saturated ammonium chloride solution.It was extracted with ethyl acetate (20 mL×3), and the dibenzothiophene derivative was separated by column chromatography, and the separation yield reached 88% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7 %Chromat. | With (1,2-bis(diisopropylphosphino)ethane)nickel(II) chloride; potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 92h; Inert atmosphere; Schlenk technique; | 4.4 Desulfurization of dibenzothiophenes and sulfones in anhydrous media General procedure: Using [Ni(dippe)Cl2] (0.02g, 0.0511mmol), added into a t-BuOK (0.0344g, 0.3066mmol) solution in THF (2mL), the color turned dark amber after 5min. Then, phenylboronic acid (0.1531mmol) and dibenzothiophene (0.0094g, 0.0511mmol), 4-MeDBT (0.0101g, 0.0511mmol) or 4,6-Me2DBT (0.0108g, 0.0511mmol) were added with constant stirring corresponding dissolved in THF (1mL). Then, the flask was heated in a silicon oil bath at 70°C for 92h. Formation of dark particles was observed during the reaction, identified as metallic nickel. After this time, the reaction mixture was cooled to RT, exposed to air, the mixture was centrifugated at 5000cycles/min to remove solids identified as metallic nickel and KCl. The organic layer was analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21 %Chromat. 2: 7 %Chromat. | With (1,2-bis(diisopropylphosphino)ethane)nickel(II) chloride; potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 92h; Inert atmosphere; Schlenk technique; | 4.4 Desulfurization of dibenzothiophenes and sulfones in anhydrous media General procedure: Using [Ni(dippe)Cl2] (0.02g, 0.0511mmol), added into a t-BuOK (0.0344g, 0.3066mmol) solution in THF (2mL), the color turned dark amber after 5min. Then, phenylboronic acid (0.1531mmol) and dibenzothiophene (0.0094g, 0.0511mmol), 4-MeDBT (0.0101g, 0.0511mmol) or 4,6-Me2DBT (0.0108g, 0.0511mmol) were added with constant stirring corresponding dissolved in THF (1mL). Then, the flask was heated in a silicon oil bath at 70°C for 92h. Formation of dark particles was observed during the reaction, identified as metallic nickel. After this time, the reaction mixture was cooled to RT, exposed to air, the mixture was centrifugated at 5000cycles/min to remove solids identified as metallic nickel and KCl. The organic layer was analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 40 %Chromat. 2: 6 %Chromat. 3: 6 %Chromat. | With (1,2-bis(diisopropylphosphino)ethane)nickel(II) chloride; potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 92h; Inert atmosphere; Schlenk technique; | 4.4 Desulfurization of dibenzothiophenes and sulfones in anhydrous media General procedure: Using [Ni(dippe)Cl2] (0.02g, 0.0511mmol), added into a t-BuOK (0.0344g, 0.3066mmol) solution in THF (2mL), the color turned dark amber after 5min. Then, phenylboronic acid (0.1531mmol) and dibenzothiophene (0.0094g, 0.0511mmol), 4-MeDBT (0.0101g, 0.0511mmol) or 4,6-Me2DBT (0.0108g, 0.0511mmol) were added with constant stirring corresponding dissolved in THF (1mL). Then, the flask was heated in a silicon oil bath at 70°C for 92h. Formation of dark particles was observed during the reaction, identified as metallic nickel. After this time, the reaction mixture was cooled to RT, exposed to air, the mixture was centrifugated at 5000cycles/min to remove solids identified as metallic nickel and KCl. The organic layer was analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 35 %Chromat. 2: 6 %Chromat. | With (1,2-bis(diisopropylphosphino)ethane)nickel(II) chloride; potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 92h; Inert atmosphere; Schlenk technique; | 4.4 Desulfurization of dibenzothiophenes and sulfones in anhydrous media General procedure: Using [Ni(dippe)Cl2] (0.02g, 0.0511mmol), added into a t-BuOK (0.0344g, 0.3066mmol) solution in THF (2mL), the color turned dark amber after 5min. Then, phenylboronic acid (0.1531mmol) and dibenzothiophene (0.0094g, 0.0511mmol), 4-MeDBT (0.0101g, 0.0511mmol) or 4,6-Me2DBT (0.0108g, 0.0511mmol) were added with constant stirring corresponding dissolved in THF (1mL). Then, the flask was heated in a silicon oil bath at 70°C for 92h. Formation of dark particles was observed during the reaction, identified as metallic nickel. After this time, the reaction mixture was cooled to RT, exposed to air, the mixture was centrifugated at 5000cycles/min to remove solids identified as metallic nickel and KCl. The organic layer was analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 0 - 50℃; for 4.1h; | 8 10mmol 4-methyldibenzothiophene was added to a 100mL eggplant bottle.10 mmol of methyl decanoate,30 mmol of trifluoromethanesulfonic acid was carefully added at 0 °C.After stirring for 10 minutes, it was heated to 50 ° C, and after 4 hours of reaction, the reaction liquid became clear.The reaction solution was then poured into 100 mL of distilled water, and 50 mL×3 was extracted with dichloromethane.The resulting organic phase was concentrated to about 10 mL.100 mL of diethyl ether was added, and the mixture was allowed to stand, and a solid precipitated. Filter and wash the solid with diethyl ether and dry. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; lithium iodide; lithium tert-butoxide at 50℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 380℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With C21H30ClNPPd; potassium <i>tert</i>-butylate In tert-Amyl alcohol at 65℃; for 18h; Sealed tube; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate / dichloromethane; hexane / -30 °C / Inert atmosphere 2: dichloromethane / 0.5 h / -40 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate / dichloromethane; hexane / -30 °C / Inert atmosphere 2: dichloromethane / 0.5 h / -40 - 20 °C / Inert atmosphere 3: 1,2-dimethoxyethane / 0.5 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: dibenzothiophene With n-butyllithium; potassium carbonate In tetrahydrofuran; water at -78℃; for 5h; Inert atmosphere; Stage #2: methyllithium In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 20℃; for 3h; Inert atmosphere; |
Tags: 7372-88-5 synthesis path| 7372-88-5 SDS| 7372-88-5 COA| 7372-88-5 purity| 7372-88-5 application| 7372-88-5 NMR| 7372-88-5 COA| 7372-88-5 structure
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