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[ CAS No. 2757-37-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2757-37-1
Chemical Structure| 2757-37-1
Chemical Structure| 2757-37-1
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Product Details of [ 2757-37-1 ]

CAS No. :2757-37-1 MDL No. :MFCD00039866
Formula : C24H50S2 Boiling Point : -
Linear Structure Formula :- InChI Key :GAYUSSOCODCSNF-UHFFFAOYSA-N
M.W : 402.78 Pubchem ID :151040
Synonyms :

Calculated chemistry of [ 2757-37-1 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 23
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 132.66
TPSA : 50.6 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -0.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 6.77
Log Po/w (XLOGP3) : 12.08
Log Po/w (WLOGP) : 10.21
Log Po/w (MLOGP) : 7.33
Log Po/w (SILICOS-IT) : 10.03
Consensus Log Po/w : 9.28

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -8.43
Solubility : 0.0000015 mg/ml ; 0.0000000037 mol/l
Class : Poorly soluble
Log S (Ali) : -13.15
Solubility : 0.0 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -9.7
Solubility : 0.0000000804 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.7

Safety of [ 2757-37-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2757-37-1 ]

* 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 [ 2757-37-1 ]

[ 2757-37-1 ] Synthesis Path-Downstream   1~87

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YieldReaction ConditionsOperation in experiment
99% With polyvinylpolypyrrolidonium tribromide; In ethanol; at 20℃; for 1.75h;Green chemistry; General procedure: A 25 mL round-bottom flask was charged with thiol (1 mmol), polyvinylpolypyrrolidoniume tribromide (1.2 gr), and EtOH(5 mL) as solvent. The reaction mixture was stirred at room temperature, and the progressof the reaction was monitored by TLC. After completion of the reaction, corresponding disulfides easily obtained by passing of reaction mixture through a short column using dichlromethane and acetone (95:5) as eluent.
92% With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 30℃; for 6h; General procedure: To a well stirred solution of Thiols (1equiv.) in THF Phenyl Trimethyl ammonium Tribromide (PTAB) (0.5 equiv) was added and the reaction was stirred at room tempearature for 4-8 hrs. After completion of the reaction which was monitored by TLC, The reaction mixture was quenched with distilled water and extracted with ethyl acetate (3X3ml). The organic fraction was washed with saturated brine solution and dried over oven dried anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. The residual crude mass was subjected to a short silica gel column filtration (petroleum ether/ethyl acetate) afforded the desired disulfane as the pure product.
90% With potassium bromate; hexaammonium heptamolybdate tetrahydrate; In water; acetonitrile; at 20℃; for 0.5h; General procedure: 4-chlorothiophenol (0.145 g, 1 mmol) was added to a heterogeneous mixture of KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24·4H2O (0.124 g, 10 mmolpercent), and CH3CN/H2O (7:3) (5 mL) and the mixture was stirred under a hood for 4 min at ambient atmosphere and room temperature. The progress of the reaction was monitored by TLC (eluent: EtOAc/n-C6H14, 1/13). After completion, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed with 5percent NaOH, water, and dried over anhydrous MgSO4. Finally, evaporation of the solvent gave the product with sufficient purity formost purposes
90% With hydrogenchloride; iodine; In dimethyl sulfoxide; EXAMPLE VII A mixture of 9 ml of DMSO (127 mmole), 12 ml of 1-dodecanethiol (50 mmole), 0.1 ml of 37 percent hydrochloric acid (1.2 mmole), and 10.8 mg of iodine (0.085 mmole as HI) was heated by a bath, while stirring magnetically, at about 60°C. After one and a fourth hours, the lower phase became amber colored. The mixture was cooled with stirring to produce fine crystals. These were filtered off and rinsed with DMSO. Recrystallization from acetone gave 9.02 g of didodecyl disulfide (90 percent of theory). Mp, 33°-5°C. (reported, 33°-4°C.).
84% With 1-n-butyl-3-methylimidazolium methylselenite; at 60℃; for 4h; Method A: In a Schlenk tube under open atmosphere and at room temperature, the corresponding thiol (1.0 mmol) was added to [bmim][SeO2(OCH3)]10 (1.0 mL). The reaction mixture was allowed to stir at 60 °C for the time indicated in Table 1. The progress of the reaction was monitored by TLC. Method B: In a 10 mL glass vial equipped with a small magnetic stirring bar, containing 1.0 mL of [bmim][SeO2(OCH3)] was added the thiol (1.0 mmol). The vial was tightly sealed with an aluminum/Teflon crimp top. The mixture was then irradiated in a microwave reactor (CEM Explorer) for the time indicated in Table 2 at 30 °C (temperature was measured with an IR sensor on the outer surface of the reaction vial), using an irradiation power of 100 W and pressure of 150 psi. After the reaction was complete, the product was extracted by successive washings with petroleum ether (3 .x. 5 mL), dried over MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate/hexanes as the eluent.
75% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper dichloride; In toluene; at 110℃; for 12h; To a reaction flask equipped with 3mL of toluene were added sequentially 0. 05mmol of TEMPO, 0. 05 mmol of CuCl2, 1 mmol dodecanethiol, substituted with an oxygen atmosphere, reflux the reaction 12 hours, the reaction was complete gussets. Direct mix sample through the column. The product was obtained in 75percent yield
73% With epolactaene; sodium hydrogencarbonate; In methanol; water; at 20℃; for 0.5h;Inert atmosphere; General procedure: To a solution of 1 (10 mg, 26 mumol) and thiol (2.2 mol equiv) in degassed MeOH (1.0 mL) was added 0.5 M aqueous solution of NaHCO3 (1.0 mL) at room temperature. The mixture was stirred at room temperature under a nitrogen atmosphere until no further change in TLC was observed. The reaction was quenched by the addition of 1 M HCl aqueous solution, and the mixture was diluted with EtOAc. The layers were separated, the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography to give the corresponding disulfide. The structures of diphenyl disulfide, 2,2'-dipyridyl disulfide, n-dihexyl disulfide and n-didodecyl disulfide were confirmed by MS analyses as well as comparison of the 1H NMR data with those of the authentic disulfides.
71% With tert.-butylnitrite; oxygen; In 1,2-dichloro-ethane; at 50℃; under 760.051 Torr; for 6h;Sealed tube; Green chemistry; General procedure: A sealed tube (90 mL) equipped with a magnetic stirring bar and an O2 balloon was charged with dichloroethane (DCE, 20 mL), thiophenol (1a, 4 mmol, 0.44 g) and TBN (0.16 mmol, 4 molpercent, 19.2 mL). Then the tube was placed in an oil bath, which was preheated to 50°C. The mixture was stirred for 1 h until starting material was completely consumed as monitored by GC and TLC. After removing the solvent, the residue was purified by column chromatography on silica gel to give the desired diphenyl disulfide (2a, 90percent, 0.394 g) as a white solid.
70% With iodine; dimethyl sulfoxide; In neat (no solvent); at 25℃; for 0.166667h;Microwave irradiation; Sealed tube; General procedure: In specific microwave tube (10.0 mL), was added iodine (51.0 mg, 20.0 molpercent), DMSO (37 muL, 1.0 mmol) and thiol (1.0 mmol), The sealed reaction tube was placed in the microwave cavity and a maximum irradiation power of 100 W was applied. When the temperature reach 25 °C the reaction was stirred for 10 minutes. After cooling the reaction system to room temperature it was quenched with ethyl acetate and the aqueous layer was extracted with Na2S2O3 (3 x 20.0 mL). The organic phase was dried over MgSO4, filtered, and the solvent was removed reduced pressure. The crude product was purified by flash column chromatography eluting with an appropriate mixture of hexane/ethyl acetate.
With propan-1-ol; tetrachloromethane; oxygen; In 2,2,4-trimethylpentane; at 175℃; for 5h;Sealed tube;Catalytic behavior; The oxidation of thiol was performed in a glass flask at room temperature under vigorous magnetic stirring. Isooctane (25 ml), a catalyst (0.1 g), and dodecane-1-thiol (5 × 10?2M) were placed in the flask; air oxygen dissolved in the reaction mixture was used as the oxidizer. The amount of thiol was measured by means of potentiometric titration with diamine silver nitrate in the presence of ion-selective argentite electrode [24]. The catalytic activity (turnover frequency (TOF)) was calculated as the ratio of the initial rate of thiol concentration decrease to the concentration of copper. The total stability (turnover number(TON)) was calculated as the ratio of oxidized thiol and copper amounts. The catalytic experiments with CCl4 were performed in sealed evacuated glass tubes as described in [22]. To prepare a standard sample, a catalyst, decane and CCl4 were placed in a glass tube. To remove dissolved air, the cycle ?freezing with liquid nitrogen-pumping out-defreezing? was repeated three times, after that the ampoule was soldered. This ampoule was placed in a thermostat, equipped with a mechanism for intense stir-ring of the mixture. The activity of the supported catalysts was characterized by the overall yield of chlorinated products(monochlorodecanes and dichlorodecanes), over a 5 h periodat 175C at the constant initial reactant ratio: 0.05 g of the heterogenous catalyst, 0.4 ml of CCl4, 0.2 ml of decane and alcohol (methanol-29 l, ethanol-42 l, isopropyl alcohol-55 l,propan-1-ol-54 l, 2-methylpropan-2-ol-68 l, butan-1-ol-66 l,pentan-1-ol-78 l).
With bis(pyridine)copper(II) dichloride; In 2,2,4-trimethylpentane; at 20℃;Catalytic behavior; Mechanism; The oxidation of thiols was carried out at room temperature and normal pressure in a flat-bottom flask with vigorous stirring, so that the reaction rate was independent of the stirring intensity. The solid catalyst (5×10?5 mole of copper) was placed in a flask and 25 ml of dodecane-1-thiol solution in isooctane was added ([RSH] = 5×10?2 M). [33] To estimate the role of copper, analogous experiments were performed without copper (the sample consisted of isooctane, thiol ([RSH] = 5×10?2 M) and the ligand (concentration 2×10?2 M)).

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[2]Journal of Chemical Research - Part S,1998,p. 816 - 817
[3]Synthesis,2008,p. 2659 - 2664
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 996
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 996
[6]Tetrahedron Letters,2005,vol. 46,p. 6097 - 6099
[7]Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,p. 433 - 439
[8]RSC Advances,2015,vol. 5,p. 31347 - 31351
[9]Journal of Chemical Research - Part S,1999,p. 374 - 375
[10]Tetrahedron Letters,2004,vol. 45,p. 8489 - 8491
[11]Tetrahedron Letters,2007,vol. 48,p. 7469 - 7471
[12]Phosphorus, Sulfur and Silicon and the Related Elements,2008,vol. 183,p. 415 - 419
[13]Journal of Organic Chemistry,2011,vol. 76,p. 4173 - 4177
[14]Journal of Organic Chemistry,1981,vol. 46,p. 2596 - 2598
[15]Synthetic Communications,1993,vol. 23,p. 1659 - 1665
[16]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 685 - 691
[17]Synthesis,2007,p. 3286 - 3289
[18]Journal of the Chemical Society. Chemical communications,1994,p. 1993 - 1994
[19]Synthetic Communications,2000,vol. 30,p. 701 - 706
[20]Synthetic Communications,2000,vol. 30,p. 1249 - 1255
[21]Journal of the American Chemical Society,2010,vol. 132,p. 13117 - 13119
[22]Organometallics,2010,vol. 29,p. 4459 - 4463
[23]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 625 - 627
[24]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 1777 - 1781
[25]Synthetic Communications,2002,vol. 32,p. 1151 - 1157
[26]Tetrahedron Letters,2018,vol. 59,p. 2360 - 2364
[27]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1997,vol. 36,p. 819 - 821
[28]Phosphorus, Sulfur and Silicon and the Related Elements,2013,vol. 188,p. 1236 - 1243
[29]Patent: US3954800,1976,A
[30]Tetrahedron Letters,2010,vol. 51,p. 6734 - 6736
[31]Organometallics,2011,vol. 30,p. 4136 - 4143
[32]Synthesis,2002,p. 856 - 858
[33]European Journal of Organic Chemistry,2010,p. 2661 - 2665
[34]Tetrahedron Letters,2011,vol. 52,p. 640 - 643
[35]Tetrahedron Letters,2003,vol. 44,p. 6789 - 6791
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[39]Patent: CN105294371,2016,A .Location in patent: Paragraph 0065; 0066; 0067; 0068; 0069; 0125-0128
[40]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4162 - 4172
[41]Chinese Chemical Letters,2016,vol. 27,p. 1505 - 1508
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[57]Organic Letters,2011,vol. 13,p. 1734 - 1737
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    Neftekhimiya,2014,vol. 54,p. 219 - 225,7
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[63]Organometallics,2017,vol. 36,p. 2588 - 2596
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  • [ 27151-73-1 ]
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  • [ 507-09-5 ]
  • 1-(S-acetyldisulfanyl)dodecane [ No CAS ]
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  • [ 51253-51-1 ]
  • [ 144640-98-2 ]
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  • 2,8-dimethyl-5-(trifluoromethyl)dibenzo[b,d]thiophenium trifluoromethanesulfonate [ No CAS ]
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  • [ 129922-44-7 ]
  • 20
  • 3,7-di-tert-butyl-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate [ No CAS ]
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  • [ 129922-44-7 ]
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  • [ 2099-87-8 ]
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  • [ 138715-77-2 ]
  • cyclohexyl dodecyl sulfide [ No CAS ]
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  • [ 80859-83-2 ]
  • 1-adamantyl dodecyl sulfide [ No CAS ]
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  • [ 2757-37-1 ]
  • <bis(pentadecanecarboxy)iodo>benzene [ No CAS ]
  • pentadecyl dodecyl sulfide [ No CAS ]
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  • [ 143-15-7 ]
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  • [ 10578-51-5 ]
  • didodecyl trisulfide [ No CAS ]
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  • 2-Benzoyl-thiobenzoic acid S-dodecyl ester [ No CAS ]
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  • [ 60456-75-9 ]
  • 28
  • [ 108-98-5 ]
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  • dodecyl phenyl disulfide [ No CAS ]
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  • [ 2487-77-6 ]
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  • S-dodecyl 2,2-dimethylpropanethioate [ No CAS ]
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  • [ 64-17-5 ]
  • sodium thiosulfate [ No CAS ]
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  • air [ No CAS ]
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  • [ 629-25-4 ]
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  • potassium peroxo disulfate [ No CAS ]
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  • [ 123-91-1 ]
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  • [ 82139-14-8 ]
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  • lead (II)-dodecyl mercaptide [ No CAS ]
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  • [ 7697-37-2 ]
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  • [ 7553-56-2 ]
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  • [ 64-19-7 ]
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  • 45
  • [ 54187-96-1 ]
  • [ 2757-37-1 ]
  • 1-dodecylsulfanylmethyl-1<i>H</i>-benzotriazole [ No CAS ]
  • 46
  • [ 86763-30-6 ]
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  • [ 87-90-1 ]
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  • [ 26960-77-0 ]
  • [ 137882-81-6 ]
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  • 2-dodecylthio-1-nitro-1-phenyl-2-p-tolylthioethane [ No CAS ]
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  • [ 26960-77-0 ]
  • [ 137908-43-1 ]
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  • 2-dodecylthio-1-nitro-1-phenylethene [ No CAS ]
  • 2-p-chlorophenylthio-2-dodecylthio-1-nitro-1-phenylethane [ No CAS ]
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  • 2-p-chlorophenylthio-2-dodecylthio-1-nitro-1-phenylethane [ No CAS ]
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  • (Z)-2,3-bis(dodecylthio)prop-2-en-1-ol [ No CAS ]
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YieldReaction ConditionsOperation in experiment
86% With hydrogen; triethylamine; In tetrahydrofuran; at 65℃; under 760.051 Torr; for 24h;Inert atmosphere; Green chemistry; General procedure: A 25 mL, three-necked round-bottom flask equipped with a refluxcondenser and a magnetic stir bar was charged sequentially withSiO2?P?RhCl(PPh3)2 (16 mg, 0.006 mmol), disulfide or diselenide(0.2 mmol), alkyl halide (0.44 mmol), THF (1.0 mL), and Et3N(0.2 mL) under argon. Then hydrogen was introduced to the resultingsuspension. The mixture was stirred at 65 °C for 24 h. After beingcooled to room temperature, the mixture was diluted with Et2O (10 mL)and filtered. The SiO2?P?RhCl(PPh3)2 complex was washed withTHF (2 × 5 mL) and Et2O (2 × 5 mL) and reused in the next run. Theether solution was concentrated under a reduced pressure, and theresidue was purified by preparative TLC (hexane) to afford the desiredproduct.
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  • [ 143-15-7 ]
  • sodium-<5.6.7.8-tetrahydro-naphtholate-(1)> [ No CAS ]
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YieldReaction ConditionsOperation in experiment
Comparative Example A; Attempted Synthesis of Bis (dodecylsuffanylthiocarbonyl) ; A 1000 mL 4-neck round bottom flask (fitted with mechanical stirrer, septum, thermocouple well, and condenser with N2 inlet) was charged with a solution of potassium t-butoxide (17.2 g, 0.153 mol) in tetrahydrofuran (200 mL). The solution was cooled to ca. 5°C and treated with dodecanethiol (30.3 g, 0.15 mol). The reaction mixture was stirred for 30 min at 5 - 10°C. The thick slurry was treated with carbon disulfide (11.8 g, 0.154 mol) over a ca. 30 min period. The mixture became yellow. The mixture was stirred at ca. 0°C for 1 h and then was allowed to warm to room temperature. The resulting yellow solution was treated in portions with iodine prills (19.0 g, 0.075 mol) over a 20 min period, keeping the temperature controlled below 28 - 30°C. When iodine addition was complete, the mixture was stirred for 1.5 h. Ethyl acetate (300 mL) was added, and the mixture was treated with water (50 mL) and then with sodium thiosulfate solution (50 mL) and stirred vigorously. The organic layer was washed twice with sodium chloride solution, dried over Na2S04, and evaporated to give only 31.6 g of almost colorless solid. 1H NMR featured a major downfield CH2S signal at 2.67, and only traces of other triplet signals in the 3.4 to 2.8 range. The mass spectrum exnibitea parent ion with m/e = 402.335, consistent with C24H50S2, bis (dodecyl) disulfide.
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  • tricapryl methyl ammonium chloride [ No CAS ]
  • [ 112-55-0 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In tetrachloromethane; water; EXAMPLE 2 202 g (1 mol) n-dodecyl mercaptan, 22 g (0.55 mol) sodium hydroxide, 100 ml water and 0.6 g (1.5 mmol) tricapryl methyl ammonium chloride are reacted as in Example 1 with 77 g (0.5 mol) tetrachloromethane. Yield of di-n-dodecyl disulfide: 198 g (99percent).
  • 62
  • [ 67-63-0 ]
  • [ 112-55-0 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
In n-heptane; EXAMPLE 4 23 g of Compound No. 9 is stirred in 100 ml of heptane with 20.2 g of n-laurylmercaptan for 4 hours. The reaction proceeds slightly exothermically; the temperature rises within 2 hours from 23° C. to 32° C. The mixture is subsequently concentrated in a rotary evaporator, and the residue is recrystallized cold from 150 ml of i-propanol: di-n-lauryl disulfide; yield: 15.2 g (75.5percent of theory); m.p. 32°-33° C. (Lit. 30°-31° C.).
  • 63
  • [ 31598-52-4 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol; COMPARATIVE EXAMPLE 1 13 g of 1-(2,4,6-trichlorophenyl)-3-{3-[(2,4-di-tert-amylphenoxy)butyramido]benzamido}-5-oxo-2-pyrazoline was added to 100 ml of 10percent ethanol solution (volume ratio of water to ethanol: 1:9), 7.7 g of didodecyl disulfide prepared by oxidizing dodecylmercaptan with hydrogen peroxide, and 1.5 g of potassium carbonate were added, and then the resulting mixture was refluxed for 1 hour under heating.
  • 64
  • [N(C2H5)3H](1+)*[HFe3(CO)11](1-)=[N(C2H5)3H][HFe3(CO)11] [ No CAS ]
  • [ 2757-37-1 ]
  • (C12H25S)2Fe2(CO)6 [ No CAS ]
  • 2C12H25S(1-)*S(2-)*4Fe(1+)*12CO=(C12H25S)2(S)Fe4(CO)12 [ No CAS ]
  • 65
  • [ 932-31-0 ]
  • [ 2757-37-1 ]
  • [ 1079988-46-7 ]
  • 66
  • [ 2757-37-1 ]
  • [ 588-72-7 ]
  • (Z)-1-(dodec-1-ylsulfanyl)-2-phenylethene [ No CAS ]
  • [ 88708-54-7 ]
  • 67
  • [ 2757-37-1 ]
  • [ 402-26-6 ]
  • [ 1079988-47-8 ]
  • 68
  • [ 2757-37-1 ]
  • [ 21970-13-8 ]
  • [ 1079988-48-9 ]
  • 69
  • [ 2757-37-1 ]
  • [ 18620-03-6 ]
  • [ 1079988-50-3 ]
  • 70
  • [ 2757-37-1 ]
  • [ 16750-63-3 ]
  • [ 1079988-49-0 ]
  • 71
  • [ 2757-37-1 ]
  • [ 100-58-3 ]
  • [ 56056-49-6 ]
  • 72
  • [ 2757-37-1 ]
  • [ 13139-86-1 ]
  • [ 867017-31-0 ]
  • 74
  • [ 917-92-0 ]
  • [ 2757-37-1 ]
  • [ 1034014-65-7 ]
  • 75
  • [ 629-05-0 ]
  • [ 2757-37-1 ]
  • [ 1034014-60-2 ]
  • 76
  • [ 2757-37-1 ]
  • [ 931-48-6 ]
  • [ 1034014-64-6 ]
  • 77
  • [ 2757-37-1 ]
  • [ 767-91-9 ]
  • [ 1034014-62-4 ]
  • 78
  • [ 2757-37-1 ]
  • [ 705-31-7 ]
  • [ 1034014-63-5 ]
  • 79
  • [ 2757-37-1 ]
  • [ 536-74-3 ]
  • [ 1034014-59-9 ]
  • 80
  • [ 2757-37-1 ]
  • [ 768-60-5 ]
  • [ 1034014-61-3 ]
  • 81
  • [ 2757-37-1 ]
  • [ 74-86-2 ]
  • [ 143570-82-5 ]
  • 82
  • [ 54489-01-9 ]
  • [ 2757-37-1 ]
  • [ 1233193-45-7 ]
  • 83
  • [ 2079-95-0 ]
  • [ 2757-37-1 ]
  • 85
  • [ 273-53-0 ]
  • [ 2757-37-1 ]
  • [ 409114-89-2 ]
  • 86
  • [ 112-53-8 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
77% General procedure: The aliphatic alcohol (1 mmol) was added to a solution of azo compound 1a or 1e (1.8 mmol) and PPh3 (1.8 mmol) in refluxing CH3CN (5 mL) and the mixture was stirred for 20 min at 80 °C. Next, NH4SCN (2.5 mmol) was added in one portion. The resulting mixture was stirred at 80 °C for the appropriate time (Table 2), until consumption of the starting material was complete, as monitored by TLC and GC analyses. The mixture was filtered and the solvent evaporated. H2O (10 mL) was added and the product was extracted with Et2O (3 × 10 mL). The organic solution was dried (MgSO4) and evaporated. The obtained residue was purified by flash column chromatography on silica gel using petroleum ether as the eluent to give the disulfide. #10;
  • 87
  • [ 2757-37-1 ]
  • [ 874-60-2 ]
  • S-(n-dodecyl) 4-methylbenzothioate [ No CAS ]
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