1986-89-6|Di-n-octylsulfoxide| Ambeed

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Quality Control of [ 1986-89-6 ] Purity: 98% SDS Specification

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Product Details of [ 1986-89-6 ]

CAS No. :	1986-89-6
Formula :	C₁₆H₃₄OS
M.W :	274.51
SMILES Code :	O=S(CCCCCCCC)CCCCCCCC
MDL No. :	MFCD00039514
Boiling Point :	No data available
InChI Key :	VWCFQNQVNVMFGV-UHFFFAOYSA-N
Pubchem ID :	74805

Safety of [ 1986-89-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1986-89-6 ]

* 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 [ 1986-89-6 ]

[ 1986-89-6 ] Synthesis Path-Downstream 1~35

1
[ 2690-08-6 ]
[ 1986-89-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1,3-dihydroxy-1H-1λ3-benzo[d][1,2]iodoxol-1-yl trifluoromethanesulfonate; In acetonitrile; at 20.0℃; for 0.166667h;Inert atmosphere;	General procedure: Sulfide 3 (0.125 mmol) was added to a solution of 2 (62 mg, 0.15 mmol) in acetonitrile (1 mL). The reaction was stirred at room temperature for 10 min to 1 h (reaction completion was controlled by TLC). After completion of the reaction, 5% aqueous Na2S2O3 (5 mL) and saturated NaHCO3 (5 mL) were added, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification using short chromatographic column (hexane-ethyl acetate = 3 : 1) afforded analytically pure sulfoxide 4.
98%	With 1,3,5-trichloro-2,4,6-triazine; urea hydrogen peroxide adduct; In acetonitrile; at 20.0℃; for 1.5h;	General procedure: To a solution of sulfide (1.0 mmol) and UHP (2.0 or 1.0 mmol according to the sulfide) in CH3CN (20 mL) wasadded cyanuric chloride (2.0 or 1.0 mmol according to the sulfide). The resulting solution was stirred until the sulfone was generated by TLC monitoring at room temperature and then quenched with H2O. The reaction mixture was extracted repeatedly with CH2Cl2. The organic layer was separated and concentrated in vacuo. The residue was subjected to flash column chromatography with hexanes/EtOAc (5:1 - 1:8) as eluent to afford the corresponding sulfoxide.
96%	With oxygen; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; ascorbic acid; In ethanol; at 30.0℃; under 760.051 Torr; for 6.0h;pH 4.0;	A mixture of dioctyl sulfide (0.128 g, 0.50 mmol), 1 (0.005 g, 0.0125 mmol) and ascorbic acid (0.264 g, 1.5 mmol) in a mixture of an aqueous 0.05 M phthalate buffer solution (4.0 mL) and ethanol (1.0 mL) was stirred vigorously at 30 C under O2 atmosphere for 6 h. The reaction mixture was extracted with ether, and the combined extracts were washed with brine, dried over MgSO4 and evaporated under reduced pressure to give dioctyl sulfoxide (0.130 g, 96%).

92%	With iodosylbenzene; VO(4-bromo-2-[(2,6-diisopropylphenylimino)methyl]phenol(-H))2; at 20.0℃; for 1.16667h;	General procedure: VO (BrDPMP)2 (0.1 mmol) and sulfide (1 mmol) were dissolved in CH2Cl2 (3 ml) and the solution was stirred for five minutes. Tothis solution PhIO was added (1.1 mmol) at once. The reaction was monitored by TLC at regular intervals and continued for stipulated reaction time. After removal of the solvent, the residue waspurified by Silica gel flash chromatography to afford sulfoxide. All the sulfoxides thus obtained were identified by comparing NMR data with values reported in the literature [8] and those of the authentic samples.
83%	With (4S,4aS,8aS)-5-ethyl-3-methyl-2′,4′:3′,5′-di-O-methylenedioxyriboflavinium perchlorate; dihydrogen peroxide; In dichloromethane; water; at 20.0℃; for 12.0h;	General procedure: A 30% aqueous solution of hydrogen peroxide (1.5 mL, 1.5 equiv) was added dropwise to a stirred mixture of sulfide (1.0 mmol) and 1 (11 mg, 0.02 mmol) in MeOH (1mL), and the mixture was stirred at ambient temperature. The progress of the reaction was monitored using gas-liquid chromatography (GLC) periodically. After the sulfide was found to be consumed, the reaction was quenched by the addition of a saturated Na2SO3 aqueous solution (1 mL) to decompose the remaining hydrogen peroxide. The reaction mixture was extracted with CH2Cl2 (1 mL × 2), dried over MgSO4, and evaporated under reduced pressure to afford sulfoxide. Structures and purity of sulfoxides were confirmed by comparison of their physical and spectral data with those reported in the literatures.
	With trans-stilbene ozonide; In methanol; at 50.0℃; for 2.0h;	5.O g of trans-stilbene (0.028 mol) suspended in 50 ml methanol at -200C was supplied with 1.2 molar equivalents of ozone. A trans-stilbene-ozonide was produced, which was present as a clear, weakly yellow solution in methanol.The solution of freshly produced ozonide wa s added drop -wise to a di-n- octylsulfide solution (7.2g / 0.028 mol) in 50 ml methanol, at 500C. Conversion was completed after 2 hours, resulting in di-n-octylsulfoxide. The selectivity was 100 %, as determined with GC-MS.
	With [Fe(2-(2′-hydroxyphenyl)-5,6-dihydro-1,3-oxazine)2Cl]; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃; for 0.25h;	General procedure: To a solution of the sulfide (0.2 mmol), chlorobenzene (0.2 mmol) as an internal standard and [Fe(N-O)2Cl] (0.01 mmol) in a 1:1 mixture of CH3OH/CH2Cl2 (1 mL) was added 0.4 mmol UHP as an oxidant. The mixture was stirred at room temperature and the reaction progress was monitored by GC. Assignments of the products were made by a comparison with authentic samples.
	With WO(O2)(salicylidene benzoyl hydrazine)(CH3OH); urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃;Catalytic behavior;	General procedure: To a solution of sulfide (0.28 mM) and catalyst (0.003 mM) in 70 : 30 mixture of CH3OH/CH2Cl2 (1.2 mL) was added urea hydrogen peroxide (UHP) (0.5 mM) as oxidant. The mixturewas stirred at room temperature, and the progress of the reaction was monitored byGC by removing small samples of the reaction mixture. To establish the identity of theproducts unequivocally, the retention times and spectral data were compared to those ofcommercially available compounds using chlorobenzene as an internal standard.
62%Chromat.	With [VO(salicylidene benzoylhydrazine)(OCH3)(CH3OH)]; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃;Catalytic behavior;	General procedure: To a solution of sulfide (0.2 mM), chlorobenzene (0.2 mM) as internal standard, and [VO(ONO)(OCH3)(CH3OH)] (0.01 mM) in a 1 : 1 mixture of CH3OH/CH2Cl2 (1 mL) wasadded 0.4 mM UHP as oxidant. The mixture was stirred at room temperature and there action progress was monitored by GC. Assignments of products were made bycomparison with authentic samples
	With C10H10MoNO7; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃; for 0.333333h;Catalytic behavior;	General procedure: To a solution of sulfide (0.2 mM), chlorobenzene (0.2 mM) as internal standard and [MoO(O2)2(phox)] (0.015 mM) in a 1 : 1 mixture of CH3OH/CH2Cl2 (1 mL), 0.4mM UHP was added as the oxidant. The mixture was stirred at room temperature and the reaction progress was monitored by GC. Assignments of products were made by comparison with authentic samples.
97%Chromat.	With dihydrogen peroxide; In water; at 50.0℃; for 4.0h;	General procedure: A test tube equipped with a magnetic stirring bar was charged with thioanisole (130.3 mg, 1.0 mmol), aqueous 35% H2O2 (247.7 mg, 2.5 mmol), and Ti-IEZ-MWW (9.9 mg). The mixture was stirred at 50C for 3 h. The conversion and yield were determined by GC analysis of the toluene solution with biphenyl as an internal standard. The yield of methyl phenyl sulfone was>99%, conversion of thioanisole was >99%, and selectivity (yield/conversion) was >99%.
	With [Fe(phox)2Cl]; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃;Catalytic behavior;	General procedure: To a solution of sulfide (0.2mmol), chlorobenzene (0.2mmol) as internal standard and [Fe(phox)2Cl] (0.01mmol) in a 1:1 mixture of CH3OH/CH2Cl2 (1mL) was added 0.4mmol UHP as a oxidant. The mixture was stirred at room temperature and the reaction progress was monitored by GC. Assignments of products were made by comparison with authentic samples.
	With (μ-oxo)diaquobis[tris(2-pyridylmethyl)amine]diiron(III) perchlorate; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃; for 0.25h;Catalytic behavior;	General procedure: For sulfide oxidation experiments, we used a standard procedure. To a solution of sulfide (0.2 mM), chlorobenzene (0.2 mM) as an internal standard and [tpa(H2O)FeOFe(H2O)tpa](ClO4)4 (0.005 mM) in a 1 : 1 mixture of CH3OH/CH2Cl2 (1 mL) 0.4 mM UHP was added as an oxidant. The mixture was stirred at room temperature and the reaction progress was monitored by GC. Assignments of the products were made by comparison with authentic samples.
	With [iron(III)(acetylacetonato)(2-(2'-hydroxyphenyl)oxazoline)2]; urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃; for 0.25h;	General procedure: The following standard procedure was used for sulfide oxidation experiments. To a solution of sulfide (0.2 mmol), chlorobenzene (0.2 mmol) as internal standard and [Fe(phox)2(acac)] (0.01 mmol) in a 1:1 mixture of CH3OH/CH2Cl2 (1 mL), was added UHP (0.4 mmol). The mixture was stirred at room temperature, and the reaction progress was monitored by GC. Products were identified by comparison with authentic samples.
84%Chromat.	With dioxo (salicylidene 2-picoloyl hydrazonato) molybdenum(VI); urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃;Catalytic behavior;	General procedure: To a solution of sulfide (0.2 mM), chlorobenzene (0.2 mM) as internal standard, and[MoO2(ONO)(CH3OH)] (0.01 mM) in a 1 : 1 mixture of CH3OH/CH2Cl2 (1 mL) was added0.2mM UHP as an oxidant. The mixture was stirred at room temperature and the reactionprogress was monitored by GC. Assignments of products were made by comparison withauthentic samples.
	With Mo12O40V(4-)*4C8H20N(1+); dihydrogen peroxide; In methanol; dichloromethane; at 20.0℃; for 2.5h;	General procedure: The oxidation reaction was carried out in a glass tube as the reaction vessel with a magnetic stirring bar. We chose oxidation of methylphenyl sulfide (MPS) by 30% H2O2 in the presence of 1 as a model reaction. To a mixture of 0.002mmol of 1 and 0.5mmol sulfide in 1mL mixture of CH3OH/CH2Cl2 (1:1) 1mmol H2O2 was added dropwise at room temperature and immediately the time of reaction was counted. The reaction progress was monitored by TLC and finally analyzed by gas chromatography. For the investigation of the influence of the reaction conditions, amount of catalyst, type and amount of oxidant, solvent type and reaction time were varied.
	With urea hydrogen peroxide adduct; In methanol; dichloromethane; at 20.0℃; for 0.5h;	General procedure: Typically, chlorobenzene (40 mL, 0.4 mmol) as the internalstandard and Mo(VI) catalyst (0.01 mmol, calculated by ICP) was added to a solution of sulfide (0.4 mmol) in (1:1) a mixture of CH3OH-CH2Cl2 (1 mL). Then, UHP (0.042 g,0.45 mmol) as the oxidant was added. The resulting mixture was stirred at room temperature for 30 min. The progress ofreaction was monitored by GC (centrifugation was used for separation of non-magnetic catalysts). After magnetic separation of the catalyst, the catalyst was washed with methanol and dichloromethane for several times and used for subsequent cycles [23].
	With dihydrogen peroxide; 14Na(1+)28H2OP2W18Co4O70(14-); In methanol; at 120.0℃; for 1.83333h;	General procedure: For a typical procedure in the oxidation of sulfides, nanocluster1 (0.0005 mmol) was added to a mixture of the sulfide substrate (0.5 mmol), H2O2 (1.0 mmol) and chlorobenzene (0.4 mmol) asan internal standard in methanol (1.0 mL) and then was stirred150 min at room temperature. The reaction completion was monitoredby Gas Chromatography (GC).
40%Chromat.	With urea hydrogen peroxide adduct; C30H26ClFeN2O4; In methanol; dichloromethane; chlorobenzene; at 20.0℃; for 1.0h;	General procedure: To a solution of sulfide (0.2 mmol), chlorobenzene (0.2 mmol)as internal standard, and catalyst (0.005 mmol) in a 1:1 mixtureof CH3OH/CH2Cl2 (1 mL) as solvent was added 0.4 mmol UHP asan oxidant. After stirring the mixture at room temperature, the reaction progress was monitored by GC, and oxidation products were assigned by matching with authentic samples (Scheme 2).

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2
[ 2004-70-8 ]
[ 1986-89-6 ]
3-methyl-2-n-heptyl-3,6-dihydro-2H-thiapyran [ No CAS ]
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