3386-35-4|Octyl 4-methylbenzenesulfonate| Ambeed

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Quality Control of [ 3386-35-4 ] Purity: 97% SDS Specification

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Product Details of [ 3386-35-4 ]

CAS No. :	3386-35-4
Formula :	C₁₅H₂₄O₃S
M.W :	284.41
SMILES Code :	O=S(C1=CC=C(C)C=C1)(OCCCCCCCC)=O
MDL No. :	MFCD00059447
InChI Key :	LYQJBZLAANNIER-UHFFFAOYSA-N
Pubchem ID :	599296

Safety of [ 3386-35-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 3386-35-4 ]

* 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 [ 3386-35-4 ]

[ 3386-35-4 ] Synthesis Path-Downstream 1~35

1
[ 3386-35-4 ]
[ 463-11-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1-butyl-3-methyl-3H-imidazol-1-ium fluoride; In neat (no solvent); at 80℃; for 0.5h;Microwave irradiation; Green chemistry;	General procedure: The starting substrate (0.5 mmol) and 1-nbutyl-3-methyl imidazolium fluoride (1.5 mmol, 3 equiv) were stirred for30 min at 80 C under microwave irradiation. The mixture was cooled to roomtemperature and the fluorinated compound was extracted with diethyl ether(3 5 mL). Organic layers were mixed and concentrated under reducedpressure. For NMR 19F determination, chlorodifluoroanisole (88 mg, 0.5 mL)was introduced as internal reference in 0.75 mL of acetone-d6. The productcould also be purified by chromatography on silica gel to afford the desiredproduct.
		Into an Erlenmeyer flask, 5.0 g of 1-methyl-3-(n-butyl)imidazolium chloride and 50 g of methanol (percentage of water content 1% by weight) were charged and dissolved. After 1.33 g of potassium fluoride and 33 g of methanol (percentage of water content 1% by weight) were charged into another Erlenmeyer flask and dissolved, two methanol solutions were mixed at 25C and the stirring was continued for 30 minutes at the same temperature. The crystalline precipitated after the reaction was filtered and washed with methanol (percentage of water content 1% by weight). The filtrate and wash liquid obtained were joined and concentrated. A white powder precipitated from the concentrated oil was removed by decantation and then the white powder was washed with a small amount of methanol. The filtrate, the washed liquid and the concentrated oil were joined and concentrated again to obtain 4.76 g of the colorless oil. Into a 50 mL flask equipped with a reflux condenser, 400 mg of the colorless oil synthesized (the fluorinating agent (1)) and 284 mg of n-octyl p-toluenesulfonate were charged and the resulting mixture was stirred for 5 hours at 80C. After cooling to room temperature, 5 g of ethyl acetate was added thereto and stirred. The mixture was separated to two layers by standing. The upper layer was analyzed by gas chromatography (internal standard method) to find that the main product was n-octyl fluoride. Yield: 98%.
	With potassium fluoride; In PEG 400;	(B) A mixture of <strong>[3386-35-4]1-octyl p-toluenesulfonate</strong> (1.45 g, 4.9 mmol) and potassium fluoride (1.43 g, 24.65 mmol) in 14 ml of PEG 400 was stirred continously at 50-55 C. for 27 hours. The reaction mixture was then treated as described in Example 1A above and gave 396 mg of a crude product containing 87.1% of the desired compound.

With potassium fluoride; In PEG 400;

B) A mixture of <strong>[3386-35-4]1-octyl p-toluenesulfonate</strong> (1.45 g, 4.9 mmol) and potassium fluoride (1.43 g, 24.65 mmol) in 14 ml of PEG 400 was stirred continously at 50-55C for 27 hours. The reaction mixture was then treated as described in Example 1A above and gave 396 mg of a crude product containing 87.1% of the desired compound.

References: [1]Tetrahedron Letters,1998,vol. 39,p. 7305 - 7306.
[2]Chemistry Letters,1987,p. 1675 - 1678.
[3]Tetrahedron Letters,2014,vol. 55,p. 826 - 829.
[4]Chemistry and industry,1958,p. 157.
[5]Patent: EP1698606,2006,A1 .Location in patent: Page/Page column 13-14.
[6]Patent: US4879068,1989,A .
[7]Patent: EP211916,1991,B1 .

2
[ 111-87-5 ]
[ 98-59-9 ]
[ 3386-35-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	General procedure: To a solution of Tscl (2.86 g, 15 mmol) and DMAP (166 mg,1 mmol) in DCM (30 mL), triethylamine (2.1 mL, 15 mmol) and hexyl alcohol (1.58 mL, 10 mmol) in DCM (20 mL) was addeddropwise at 0 C, and the mixture was allowed warm to rt andstirred for 1 h, the solvent was evaporated in vacuo, the residuewasdissolved by ethyl acetate (EA) and washed with satd aq NaHCO3,the organic layer was dried with Na2SO4, filtered, concentrated, andpurified by column chromatography to afford 11 as yellow solid(2.7 g, 95%).
	With pyridine; In dichloromethane;	General procedure: Alcohol (8.74 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol or 3.13 g of octanol, 24 mmol) and tertiary amine (30 mmol, triethylamine (4.2 ml) in the case of fluorinated alcohol and pyridine (2.4 ml) in the case of octanol) were dissolved in 50 ml of dichloromethane and p-toluenesulfonyl chloride (4.77 g, 25 mmol) was added in small portions. The reaction mixture was stirred overnight. The dichloromethane solution was then washed with water, dried over anhydrous MgSO4 and evaporated in vacuo. The crude product was crystallized from methanol in the case of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl tosylate. Crude octyl tosylate was used in the next step without further purification.
	With pyridine; at 10 - 20℃; for 3h;	General procedure: 4-Methylbenzenesulphonyl chloride (55 mmol) was added slowly to a mixture of a primary alcohol (50 mmol) and 20 ml of pyridine at 10 C. The reaction mixture was stirred for 3 h at 20 C. After that 120 ml of 25 % hydrochloric acid was slowly added. The reaction mixture was then extracted with chloroform, organic layer dried with Na2SO4 and evaporated to yield alkyl 4-methylbenzenesulphonate as colourless oily liquid or white solid, which was used without further purification. Ethyl 4-methylbenzenesulphonate was purchased from Fluka.

With trimethylamine hydrochloride; triethylamine; In acetonitrile; at 0℃; for 1h;

General procedure: The reaction of 1-octanol, 2-octanol, phenol and piperidine was performed according to the method described by Yoshida et al. 20 The activating agent, TsCl or CymCl, was present in 1.50 molar equivalents and dissolved in 1 mL of the chosen solvent. The solution was added drop-wise to a reagent mixture composed of 1.00 mmol of the chosen nucleophile, 1 molar equivalent of Me3N.HCl in 2.5 molar equivalents of Et3N, all dissolved in 1 mL of the chosen solvent in ice bath under magnetic stirring. The solvent was toluene, p-cymene or acetonitrile. After one hour, the reaction mixture was quenched with water, extracted with ethyl acetate, then washed with brine, dried with MgSO4 and concentrated in vacuo to give the crude arylsulphonyl derivative of the substrate that was analyzed by GC-FID, GC-MS, NMR spectroscopy and IR spectroscopy as appropriate. The conversion was calculated using GC-FID of the crude mixture against a calibration curve.

References: [1]Tetrahedron,1999,vol. 55,p. 2183 - 2192.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 11212 - 11215.
[3]Synthesis,1999,p. 1633 - 1636.
[4]Organic Letters,2009,vol. 11,p. 1757 - 1759.
[5]Catalysis Communications,2011,vol. 12,p. 1477 - 1482.
[6]Tetrahedron,2014,vol. 70,p. 7763 - 7769.
[7]Tetrahedron,1999,vol. 55,p. 2183 - 2192.
[8]Tetrahedron,2007,vol. 63,p. 5083 - 5087.
[9]Synlett,2012,vol. 23,p. 2692 - 2698,7.
[10]Journal of Molecular Catalysis A: Chemical,2011,vol. 351,p. 41 - 45.
[11]New Journal of Chemistry,2017,vol. 41,p. 4743 - 4746.
[12]Organic Letters,2017,vol. 19,p. 4413 - 4415.
[13]Chemical Communications,2020,vol. 56,p. 11855 - 11858.
[14]Journal of Organic Chemistry,1993,vol. 58,p. 3791 - 3793.
[15]Journal of the Chemical Society. Perkin transactions I,1998,p. 1913 - 1917.
[16]Journal of the Chemical Society,1953,p. 1785,1791.
[17]Journal of Organic Chemistry,1970,vol. 35,p. 973 - 978.
[18]Chemical Communications,1998,p. 2341 - 2342.
[19]Tetrahedron,2001,vol. 57,p. 4365 - 4370.
[20]Synthetic Communications,2002,vol. 32,p. 2651 - 2655.
[21]Journal of Organic Chemistry,2003,vol. 68,p. 6710 - 6715.
[22]Journal of Fluorine Chemistry,2014,vol. 164,p. 10 - 17.
[23]Chinese Chemical Letters,2014,vol. 25,p. 1643 - 1647.
[24]European Journal of Medicinal Chemistry,2015,vol. 93,p. 263 - 273.
[25]Journal of the American Chemical Society,2015,vol. 137,p. 5686 - 5694.
[26]Journal of the Brazilian Chemical Society,2015,vol. 26,p. 1914 - 1919.

3
[ 2346-00-1 ]
[ 3386-35-4 ]
[ 7087-08-3 ]

References: [1]Journal of Medicinal Chemistry,1966,vol. 9,p. 391 - 394.

4
[ 3386-35-4 ]
[ 591-51-5 ]
[ 2189-60-8 ]

References: [1]Organic Letters,2009,vol. 11,p. 4306 - 4309.
[2]Journal of the American Chemical Society,1973,vol. 95,p. 7777 - 7782.

5
[ 3386-35-4 ]
[ 603-35-0 ]
[ 105541-66-0 ]

References: [1]Chemical Communications,1998,p. 2341 - 2342.
[2]European Journal of Inorganic Chemistry,2006,p. 437 - 446.
[3]Chemische Berichte,1964,vol. 97,p. 2534 - 2538.

6
[ 70690-19-6 ]
[ 98-59-9 ]
[ 3386-35-4 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 763 - 765.
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4770 - 4772.
[3]Tetrahedron Letters,1989,vol. 30,p. 1665 - 1668.

7
[ 868-84-8 ]
[ 3386-35-4 ]
[ 3698-95-1 ]

References: [1]Synthesis,1983,p. 630 - 632.

8
[ 64-17-5 ]
[ 201230-82-2 ]
[ 3386-35-4 ]
[ 929-61-3 ]
[ 123-29-5 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3091 - 3094.

9
[ 3386-35-4 ]
[ 32657-89-9 ]
[ 5732-02-5 ]

References: [1]Tetrahedron Letters,1983,vol. 24,p. 1003 - 1006.

10
[ 3386-35-4 ]
[ 111-65-9 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 3891 - 3898.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 3389 - 3391.
Angew. Chem.,2017,vol. 129,p. 3438 - 3441,4.
[3]Chemistry Letters,1983,p. 795 - 796.
[4]Journal of Organic Chemistry,1980,vol. 45,p. 2550 - 2551.
[5]Chemistry Letters,1983,p. 795 - 796.

11
[ 3386-35-4 ]
[ 111-87-5 ]
[ 463-11-6 ]

References: [1]Synthesis,1987,p. 920 - 921.

12
[ 3386-35-4 ]
[ 629-27-6 ]

References: [1]Australian Journal of Chemistry,2014,vol. 67,p. 1360 - 1361.
[2]Synlett,2012,vol. 23,p. 2692 - 2698,7.
[3]Journal of Organic Chemistry,1994,vol. 59,p. 4687 - 4688.
[4]Journal of Organic Chemistry,1995,vol. 60,p. 5954 - 5957.

13
[ 3386-35-4 ]
[ 822-27-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; In water; at 40℃; for 2h;	General procedure: A mixture of benzyl chloride (2.0 mmol) and PMOxT (I) (3.0mmol) was added to aflask containing 0.5 mL H2O. The reaction continued at room temperature under atmospheric conditions until completion. The reaction progress was monitored by thin-layer chromatography. The reaction mixture was then filtered, CH2Cl2 (10 ml) was added to the filtrate and the mixture was washed with H2O (2×10 ml). The organic layer was dried over anhydrous Na2SO4. The solvent was evaporated to yield the crude dibenzyl disulfide, which was purified by preparative chromatography (silica gel, n-hexane-ethylacetate, 20: 1).
83%	With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; sodium carbonate; thiourea; In water; acetonitrile; at 80℃; for 6h;	General procedure: To a solution of thiourea (2.1 mmol, 0.160 g) and benzyl chloride (2 mmol, 0.23 mL) in wet CH3CN (3 mL CH3CN + 0.2 mL H2O), 4,4-azopyridine (1.1mmol, 0.202 g) and Na2CO3 (3 mmol, 0.318 g) were added. The mixture was stirred magneticallyat 80C. The progress of the reaction was monitored by TLC or GC until the benzyl chloridewas consumed. After completion of the reaction, the mixture was filtered through a sintered glassfunnel to remove the produced pyridine hydrazine. The solvent was evaporated under reducedpressure and the so-obtained residue was purified by flash chromatography on silica gel withpetroleum ether as eluent to provide benzyl disulfide. Dioctyl disulfide (4d) colorless oil; 1H NMR (250 MHz, CDCl3): δ 0.79-0.85 (t, J = 6.6 Hz,6H), 1.09-1.37 (m, 20H), 1.53-1.68 (m, 4H), 2.62 (t, J = 7.4 Hz, 4H); 13C NMR (62.5 MHz,CDCl3): δ 39.2, 33.9, 32.7, 31.9, 29.2, 28.8, 22.6, 14.0. Anal. Calcd. C16H34S2: C, 66.14%; H,11.79%; S, 22.07%. Found: C, 66.08%; H, 11.89%; S, 22.03%.
80%	With sulfur; potassium hydroxide; In water; at 60℃; for 0.5h;Green chemistry;	General procedure: RX (2.0 mmol), S (0.064 g, 2.0 mmol) and KOH (0.224 g,4 mmol) were added a flask containing H2O (0.5 mL). The reaction mixture was stirred at 60C under atmospheric conditions until completion (30 min). Upon completion of the reaction, the mixture was extracted with CH2Cl2 (3 × 5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. After, the residue was purified by plate chromatography to afford the corresponding product. Diselenides were synthesized analogously starting from selenium powder.

References: [1]Gazzetta Chimica Italiana,1982,vol. 112,p. 461 - 464.
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2008,vol. 183,p. 178 - 182.
[3]Journal of Sulfur Chemistry,2017,vol. 38,p. 134 - 141.
[4]Journal of the Iranian Chemical Society,2013,vol. 10,p. 201 - 205.
[5]Journal of Sulfur Chemistry,2015,vol. 36,p. 544 - 555.
[6]Phosphorus, Sulfur and Silicon and the Related Elements,2018,vol. 193,p. 41 - 44.
[7]Tetrahedron,2014,vol. 70,p. 7763 - 7769.

14
[ 3386-35-4 ]
[ 7438-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In methanol; at 50℃;Kinetics;	General procedure: Stock solutions of NaN3, NaOMe and NaI (0.6 M in MeOH-d4 and DMSO-d6) were prepared prior to the kinetics experiments. For kinetic experiments below room temperature, 0.75 mL of the required 0.6 M stock solution, and 5-10 mg of internal standard (toluene for 1H NMR and trifluorotoluene for 19F NMR) were placed into an NMR tube and the tube cooled to the desired temperature inside the NMR instrument. Then, 0.22 mmol of substrate previously dissolved in 0.25 mL of deuterated solvent were added to the NMR tube. The reaction was then followed by measurementof the decrease of one particular NMR signal with respect to the internal standard up to 30% of the reaction. For kinetic experiments above room temperature, 0.22 mmol of substrate in 0.25 mL of deuterated solvent were placed into an NMR tube, and then 0.75 mL of the corresponding 0.6 M stock solution and 5-10 mg of internal standard were added. The NMR tube was warmed to the desired temperature and the reaction followed by NMR up to 30% of the reaction.

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 3774 - 3777.
[2]Synlett,2000,p. 1673 - 1675.
[3]Journal of Organic Chemistry,2003,vol. 68,p. 6710 - 6715.
[4]Journal of Fluorine Chemistry,2012,vol. 135,p. 167 - 175.
[5]Chinese Chemical Letters,2014,vol. 25,p. 1643 - 1647.

15
[ 3386-35-4 ]
[ 882-33-7 ]
[ 13910-16-2 ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 3490 - 3493.

16
[ 86-79-3 ]
[ 3386-35-4 ]
[ 137280-05-8 ]
BSc₄₀₂₉ [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 5681 - 5688.

17
[ 3386-35-4 ]
[ 111-88-6 ]

References: [1]Synthesis,1995,p. 373 - 375.
[2]Synthetic Communications,1995,vol. 25,p. 2655 - 2663.

18
[ 3386-35-4 ]
[ 111-83-1 ]

References: [1]Synlett,2012,vol. 23,p. 2692 - 2698,7.
[2]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 607 - 608.

19
[ 100-42-5 ]
[ 3386-35-4 ]
[ 4537-13-7 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 5977 - 5983.
[2]Tetrahedron Letters,1998,vol. 39,p. 9201 - 9204.

20
[ 103-82-2 ]
[ 3386-35-4 ]
[ 57746-61-9 ]