[ CAS No. 1774-36-3 ] {[proInfo.proName]}

Name: 1774-36-3|4,4'-Sulfinylbis(methoxybenzene)|97%
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Quality Control of [ 1774-36-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1774-36-3 ]

Product Details of [ 1774-36-3 ]

CAS No. :	1774-36-3	MDL No. :	MFCD08443609
Formula :	C₁₄H₁₄O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LEDPSBGADKSDKI-UHFFFAOYSA-N
M.W :	262.32	Pubchem ID :	238614
Synonyms :

Calculated chemistry of [ 1774-36-3 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.14
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.68
TPSA :	54.74 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.85
Log Po/w (XLOGP3) :	2.65
Log Po/w (WLOGP) :	3.74
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	2.29
Consensus Log Po/w :	2.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.37
Solubility :	0.113 mg/ml ; 0.000431 mol/l
Class :	Soluble
Log S (Ali) :	-3.45
Solubility :	0.0929 mg/ml ; 0.000354 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.19
Solubility :	0.00169 mg/ml ; 0.00000646 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.5

Safety of [ 1774-36-3 ]

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 [ 1774-36-3 ]

* 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 [ 1774-36-3 ]
Downstream synthetic route of [ 1774-36-3 ]

[ 1774-36-3 ] Synthesis Path-Upstream 1~12

1
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1] Synlett, 1999, # 9, p. 1397 - 1398
[2] Synlett, 2003, # 13, p. 2029 - 2032
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 10, p. 2085 - 2091
[4] Synlett, 2002, # 5, p. 784 - 786
[5] Synthetic Communications, 2004, vol. 34, # 4, p. 743 - 750
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, # 2, p. 107 - 114
[7] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4727 - 4732
[8] Organic Letters, 2017, vol. 19, # 4, p. 838 - 841
[9] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[10] Journal of the Chemical Society, 1908, vol. 93, p. 756[11] Journal of the Chemical Society, 1906, vol. 89, p. 697
[12] Chemische Berichte, 1909, vol. 42, p. 3321
[13] Recueil des Travaux Chimiques des Pays-Bas, 1911, vol. 30, p. 385
[14] Chemische Berichte, 1894, vol. 27, p. 2548
[15] Journal of the Indian Chemical Society, 2007, vol. 84, # 7, p. 679 - 682
[16] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 7, p. 1470 - 1482
[17] Chemistry - A European Journal, 2012, vol. 18, # 11, p. 3136 - 3140

2
[ 13139-86-1 ]
[ 1774-36-3 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 1179
[2] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 5, p. 779 - 782
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 47, p. 15539 - 15543[4] Angew. Chem., 2018, vol. 130, p. 15765 - 15769,5

3
[ 3393-77-9 ]
[ 1774-36-3 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 18, p. 6208 - 6213
[2] Journal of Organic Chemistry, 1990, vol. 55, # 4, p. 1323 - 1328
[3] Synlett, 2004, # 2, p. 347 - 349
[4] RSC Advances, 2014, vol. 4, # 76, p. 40505 - 40510
[5] Synlett, 2010, # 10, p. 1557 - 1561
[6] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4253 - 4259
[7] Journal of the American Chemical Society, 1946, vol. 68, p. 973,974, 976, 2671[8] Journal of the American Chemical Society, 1947, vol. 69, p. 644,2310
[9] Chemische Berichte, 1894, vol. 27, p. 2548
[10] Tetrahedron Letters, 1990, vol. 31, # 32, p. 4533 - 4536
[11] Tetrahedron Letters, 1987, vol. 28, # 49, p. 6201 - 6204
[12] Journal of the American Chemical Society, 1988, vol. 110, p. 494
[13] Synthetic Communications, 2007, vol. 37, # 18, p. 3089 - 3093
[14] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2009, vol. 48, # 3, p. 346 - 351
[15] Synthetic Communications, 2011, vol. 41, # 20, p. 2993 - 2996

4
[ 13139-86-1 ]
[ 499140-11-3 ]
[ 1774-36-3 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 1, p. 75 - 78

5
[ 13139-86-1 ]
[ 499140-12-4 ]
[ 1774-36-3 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 1, p. 75 - 78

6
[ 951-92-8 ]
[ 945-51-7 ]
[ 1774-36-3 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 22, p. 6341 - 6348

7
[ 3393-77-9 ]
[ 1774-36-3 ]
[ 3112-80-9 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4253 - 4259
[2] Synthetic Communications, 1986, vol. 16, # 10, p. 1206 - 1216

8
[ 7719-09-7 ]
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 21, p. 2151 - 2153

9
[ 1013-23-6 ]
[ 3393-77-9 ]
[ 132-65-0 ]
[ 1774-36-3 ]

Reference： [1] Journal of Organic Chemistry, 2001, vol. 66, # 13, p. 4576 - 4579

10
[ 118268-73-8 ]
[ 1774-36-3 ]
[ 3393-77-9 ]
[ 3112-80-9 ]
[ 1153-43-1 ]
[ 28658-34-6 ]
[ 100-66-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1957 - 1960

11
[ 7446-70-0 ]
[ 7791-25-5 ]
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1911, vol. 30, p. 385

12
[ 1774-36-3 ]
[ 80-09-1 ]

Reference： [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132

[ 1774-36-3 ] Synthesis Path-Downstream 1~88

1
[ 1774-36-3 ]
[ 3112-80-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1957 - 1960
[2]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. 107 - 114
[3]Journal of the American Chemical Society,1981,vol. 103,p. 3832 - 3837
[4]Journal of Organic Chemistry,1993,vol. 58,p. 5055 - 5059
[5]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[6]Journal of the Chemical Society,1908,vol. 93,p. 756
Journal of the Chemical Society,1906,vol. 89,p. 697
[7]Magnetic Resonance in Chemistry,1989,vol. 27,p. 360 - 367
[8]Journal of the Chemical Society. Chemical communications,1982,p. 1352 - 1353
[9]Journal of Chemical Research, Miniprint,2000,p. 1118 - 1133
[10]Journal of the Indian Chemical Society,2007,vol. 84,p. 679 - 682

2
[ 1774-36-3 ]
[ 1774-34-1 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

3
[ 3393-77-9 ]
[ 1774-36-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3048 - 3055
[2]Journal of Organic Chemistry,2010,vol. 75,p. 6208 - 6213
[3]RSC Advances,2020,vol. 10,p. 10661 - 10665
[4]Journal of Organic Chemistry,1990,vol. 55,p. 1323 - 1328
[5]Synlett,2004,p. 347 - 349
[6]RSC Advances,2014,vol. 4,p. 40505 - 40510
[7]Synlett,2010,p. 1557 - 1561
[8]Journal of Organic Chemistry,1997,vol. 62,p. 4253 - 4259
[9]Journal of the American Chemical Society,1946,vol. 68,p. 973,974, 976, 2671
Journal of the American Chemical Society,1947,vol. 69,p. 644,2310
[10]Chemische Berichte,1894,vol. 27,p. 2548
[11]Tetrahedron Letters,1990,vol. 31,p. 4533 - 4536
[12]Tetrahedron Letters,1987,vol. 28,p. 6201 - 6204
[13]Journal of the American Chemical Society,1988,vol. 110,p. 494
[14]Synthetic Communications,2007,vol. 37,p. 3089 - 3093
[15]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2009,vol. 48,p. 346 - 351
[16]Synthetic Communications,2011,vol. 41,p. 2993 - 2996

4
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1]Synlett,1999,p. 1397 - 1398
[2]Synlett,2003,p. 2029 - 2032
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 2085 - 2091
[4]Synlett,2002,p. 784 - 786
[5]Synthetic Communications,2004,vol. 34,p. 743 - 750
[6]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. 107 - 114
[7]Chemistry - A European Journal,2016,vol. 22,p. 4727 - 4732
[8]Organic Letters,2017,vol. 19,p. 838 - 841
[9]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[10]Journal of the Chemical Society,1908,vol. 93,p. 756
Journal of the Chemical Society,1906,vol. 89,p. 697
[11]Recueil des Travaux Chimiques des Pays-Bas,1911,vol. 30,p. 385
[12]Chemische Berichte,1894,vol. 27,p. 2548
[13]Journal of the Indian Chemical Society,2007,vol. 84,p. 679 - 682
[14]Phosphorus, Sulfur and Silicon and the Related Elements,2011,vol. 186,p. 1470 - 1482
[15]Chemistry - A European Journal,2012,vol. 18,p. 3136 - 3140

5
[ 13139-86-1 ]
[ 1774-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In tetrahydrofuran; at 0 - 20℃; for 2h;	General procedure: Typical Procedure for Diaryl Sulfide. To a solution ofSOCl2 (1.5 mmol) in dry THF (10 mL) was added drop-wise aryl magnesium halide (3.0 mmol in THF or Et2O) at0 C. The resulting solution was stirred for 2 h at a slowrising from 0 C to room temperature. To the reaction mix-ture were added dropwise a solution of PPh3 (3.0 mmol) in dry THF (2 mL) via cannula and subsequently additionalSOCl2 (3.0 mmol) at room temperature. The resulting solu-tion was stirred until the sulfoxide intermediate was con-sumed completely by TLC (thin layer chromatography)monitoring at room temperature and quenched withH2O. The reaction mixture was extracted with Et2O andH2O. The organic layer was separated, dried over Na2SO4,and concentrated. The residue was subjected to columnchromatography with only hexanes or hexanes-EtOAc(30:1 - 20:1) as eluent to afford the corresponding sulfide.

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1910,vol. 150,p. 1179
[2]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 779 - 782
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 15539 - 15543
Angew. Chem.,2018,vol. 130,p. 15765 - 15769,5

6
[ 1774-36-3 ]
[ 3393-77-9 ]
[ 3112-80-9 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 6201 - 6204

7
[ 3393-77-9 ]
[ 1774-36-3 ]
[ 3112-80-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 4253 - 4259
[2]Synthetic Communications,1986,vol. 16,p. 1206 - 1216

8
[ 951-92-8 ]
[ 945-51-7 ]
[ 1774-36-3 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6341 - 6348

9
[ 118268-73-8 ]
[ 1774-36-3 ]
[ 3393-77-9 ]
[ 3112-80-9 ]
[ 1153-43-1 ]
[ 28658-34-6 ]
[ 100-66-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1957 - 1960

10
[ 7446-70-0 ]
[ 7791-25-5 ]
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1911,vol. 30,p. 385

13
[ 3393-77-9 ]
[ 64-19-7 ]
CrO₃ [ No CAS ]
[ 1774-36-3 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 973,974, 976, 2671
Journal of the American Chemical Society,1947,vol. 69,p. 644,2310

14
[ 1774-36-3 ]
[ 64-19-7 ]
KMnO₄ [ No CAS ]
[ 3112-80-9 ]

Reference： [1]Journal of the Chemical Society,1908,vol. 93,p. 756
Journal of the Chemical Society,1906,vol. 89,p. 697

15
[ 1013-23-6 ]
[ 3393-77-9 ]
[ 132-65-0 ]
[ 1774-36-3 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 4576 - 4579

16
[ 1774-36-3 ]
[ 3393-77-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With phosphorus trichloride; In acetonitrile; at 25℃; for 0.5h;Schlenk technique;	The synthesized thioether compound is: (bis(4-methoxyphenyl) sulfide)Add sulfoxide compound (0.5 mmol) and acetonitrile (2.0 mL) to a dry 15 mL schlenck tube, then add phosphorus trichloride (0.525 mmol) to the schlenck tube with a syringe at 25 C. The reaction time (ie, after completion of the reaction) was determined to be 0.5 h. After the reaction was completed, the thioether compound was separated from the solvent and POCl3by column chromatography toobtain a white solid, and the yield of the thioether compound was 99. %.
96%	With sodium iodide; at 20℃; for 4h;Green chemistry;	General procedure: To a solution of a sulfoxide (1 mmol) in PEG-200 (1 ml), silica sulfuric acid (374 mg, equal to 2.2 mmol H+) and NaI (2.2 mmol) were added. The mixture was stirred magnetically at room temperature and the progress of the reaction was monitored by TLC or GC until the starting sulfoxide was completely consumed. The reaction mixture was then neutralized using NaOH solution (0.5 M, 1 ml), and subsequently the enough well-powdered Na2S2O3 · 5H2O was added to mixture with stirring to react with iodine. The mixture was then extracted with EtOAc (5 × 1 ml). The organic layers were decanted, combined, dried over Na2SO4, filtered and concentrated. The crude product was further purified by silica gel chromatography using n-hexane as eluent to provide the desired product in excellent yields.
92%	With tantalum pentachloride; sodium iodide; In acetonitrile; at 20℃; for 0.0833333h;	General procedure: In a 10 mL round-bottom flask, to a solution of diphenylsulfoxide (202 mg, 1.0mmol) in CH3CN (4 mL), tantalum (IV) chloride (179 mg, 0.5 mmol) and sodium iodide (300 mg, 2.0 mmol) were added at room temperature. The mixture turned dark brown almost immediately and the progress of the reaction was followed by TLC. After completion of the reaction (3 min), the reaction mixture was diluted with water and then extracted with ethyl acetate. The combined organic extracts were washed successively with 10% aq Na2S2O3 and H2O. The organic layer was separated and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified through silicagel column chromatography (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%).

90%	With indium; tantalum pentachloride; In acetonitrile; at 20℃; for 3h;Sonication;	General procedure: Indium powder (229 mg, 2.0 mmol) and tantalum(V) chloride(358mg, 1.0mmol)weremixed inCH3CN(5 mL). The resultingmixture was sonicated for 0.5 h to produce a solution of the lowvalenttantalum-indium complex. Diphenyl sulfoxide (101 mg,0.5 mmol) was then added to this solution and the reactionmixturewas stirred for 3.0 h at room temperature. The progressof the reaction was followed by TLC. On completion, the solventwas removed under reduced pressure and the residue wasextracted successively with ethyl acetate, washed with water andbrine. The organic layerwas separated and dried over anhydrousNa2SO4. The crude product was purified by column chromatographyon silica gel (hexane:ethyl acetate=2:1) to afford diphenylsulfide (86mg, 92%). All of the productswere identified by comparisonof their spectroscopic data with authentic samples.
89%	With silica bromide; In dichloromethane; at 20℃; for 0.116667h;Inert atmosphere;	General procedure: In a typical procedure, diphenyl sulfoxide (2.2 g, 0.01 mol) and brominated silica (18.18 g, 40 mmole Br/g silica) are mixed in an aprotic solvent, e.g. dichloromethane (2 mL) or carbon tetrachloride, at room temperature with exclusion of atmospheric moisture, for 5 min. Diphenyl sulfide is isolated in pure state by simple filtration and evaporation of the solvent (1.84, 99%).
88%	With hafnium tetrachloride; zinc; In acetonitrile; at 20℃; for 3h;	General procedure: Diphenylsulfoxide (101 mg, 0.5 mmol) and hafnium(IV) chloride (320 mg, 1.0 mmol) were mixed in CH3CN (5 mL) and zinc powder (131 mg, 2.0 mmol) was then added to this solution. The whole mixture was stirred for 3 h at room temperature and the progress of the reaction was followed by TLC. On completion, the solvent was removed under reduced pressure and the residue was extracted successively with ethyl acetate, washed with water and brine. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on a silica gel (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%). All of the products were identified by comparison of their spectroscopic data with authentic samples.[34]
	With thionyl chloride; triphenylphosphine; In tetrahydrofuran; at 20℃; for 7h;	General procedure: Typical Procedure for Diaryl Sulfide. To a solution ofSOCl2 (1.5 mmol) in dry THF (10 mL) was added drop-wise aryl magnesium halide (3.0 mmol in THF or Et2O) at0 C. The resulting solution was stirred for 2 h at a slowrising from 0 C to room temperature. To the reaction mix-ture were added dropwise a solution of PPh3 (3.0 mmol) in dry THF (2 mL) via cannula and subsequently additionalSOCl2 (3.0 mmol) at room temperature. The resulting solu-tion was stirred until the sulfoxide intermediate was con-sumed completely by TLC (thin layer chromatography)monitoring at room temperature and quenched withH2O. The reaction mixture was extracted with Et2O andH2O. The organic layer was separated, dried over Na2SO4,and concentrated. The residue was subjected to columnchromatography with only hexanes or hexanes-EtOAc(30:1 - 20:1) as eluent to afford the corresponding sulfide.

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 6328 - 6331
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1200 - 1204
[3]Patent: CN110041236,2019,A .Location in patent: Paragraph 0127-0131
[4]European Journal of Organic Chemistry,2020,vol. 2020,p. 3009 - 3012
[5]Journal of Sulfur Chemistry,2013,vol. 34,p. 259 - 263
[6]Synthetic Communications,2003,vol. 33,p. 53 - 57
[7]Phosphorus, Sulfur and Silicon and the Related Elements,2011,vol. 186,p. 1470 - 1482
[8]Synthetic Communications,2007,vol. 37,p. 3089 - 3093
[9]Synthetic Communications,2007,vol. 37,p. 4079 - 4083
[10]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 2525 - 2526
[11]Synthetic Communications,2013,vol. 43,p. 2057 - 2061
[12]Synthetic Communications,2002,vol. 32,p. 63 - 68
[13]Journal of Sulfur Chemistry,2017,vol. 38,p. 597 - 603
[14]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 807 - 810
[15]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189
[16]Synthetic Communications,2011,vol. 41,p. 2993 - 2996
[17]Journal of Sulfur Chemistry,2014,vol. 35,p. 7 - 13
[18]Journal of Sulfur Chemistry,2015,vol. 36,p. 358 - 363
[19]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 779 - 782
[20]Journal of the American Chemical Society,2018,vol. 140,p. 9203 - 9210

17
[ 13139-86-1 ]
[ 499140-11-3 ]
[ 1774-36-3 ]
(1R,2S)-2-[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-p-methoxybenzenesulfinate [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 75 - 78

18
[ 108-86-1 ]
[ 1774-36-3 ]
bis(4-methoxyphenyl)phenylsulfonium bromide [ No CAS ]

Reference： [1]Synthesis,2004,p. 1648 - 1654

19
[ 13139-86-1 ]
[ 499140-12-4 ]
[ 1774-36-3 ]
(1R,2S)-2-[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-p-methoxybenzenesulfinate [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 75 - 78

20
[ 1774-36-3 ]
[ 80-09-1 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

21
[ 1774-36-3 ]
[ 77-46-3 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

22
[ 1774-36-3 ]
[ 47225-87-6 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

23
[ 1774-36-3 ]
[ 5456-51-9 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

24
[ 1774-36-3 ]
[ 80-08-0 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

25
[ 101-84-8 ]
[ 1774-36-3 ]
C₂₆H₂₃O₃S⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		To a one liter flask provided with a calcium chloride tube, a thermometer and a mechanical stirrer, 25 g of phosphorus oxide and 160 g of methanesulfonic acid were added, and stirred for three hours at an interior temperature at about 80 C. After being set aside to room temperature, 44 g of <strong>[1774-36-3]bis(4-methoxyphenyl)sulfoxide</strong> and 43 g of phenyl ether were added and stirred for three hours while cooling the flask with water. To a two liter conical beaker, 31 g of potassium hexafluorophosphate was added to dissolve into one liter of iced water, after which the above reacted solution was added a little at a time while mechanically stirred to obtain a soft white amorphous material. After stopping of stirring, the supernatant liquid was removed by decanting. To the residue, one liter of methylene chloride was added. After water washing, the methylene chloride layer was vacuum concentrated to obtain a crude product, which was refined using an activated alumina column treatment, and the solvent was vacuum concentrated to obtain a light brown, oily component. To the component, 1,000 ml of hexane was added and the resulting crystals were filtered to obtain TAS-2. The yield goal was 72.4 g (the yield being 77%). The crystals were identified as the specified substance using a [0125] 1H-NMR and a mass spectrometry

Reference： [1]Patent: US2004/244641,2004,A1 .Location in patent: Page 17

26
[ 1774-36-3 ]
[ 108-88-3 ]
C₂₁H₂₁O₂S⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		Added to a one liter flask provided with a calcium chloride tube and a thermometer were, 36 g of phosphorus oxide and 180 g of methanesulfonic acid, after which the contents were stirred and heated for three hours at a temperature of about 80 C. After allowed to cool to room temperature, 60.6 g of <strong>[1774-36-3]bis(4-methoxyphenyl)sulfoxide</strong> and 21.3 g of toluene were added. This resulted in a drastic temperature rise due to chemical reaction, so immediate cooling with water was conducted while stirring for another three hours. Added to a two liter conical beaker was, 49 g of potassium hexafluorophosphate and dissolved into one liter of ice cold water, after which the above reacted solution was added bit by bit while mechanically stirred to result in a liver colored, nougat-like amorphous material. After stirring, the supernatant liquid was decanted. Added to the residue, was 800 ml of methylene chloride, followed by a solution of 25 g of hexafluorophosphoric acid/500 ml of purified water, and dispersed for one hour. After draining off the water layer, the remaining methylene chloride layer was vacuum concentrated to obtain the crude product, which was refined using an activated alumina column treatment, after which the solvent was vacuum concentrated to obtain a light brown, oily compound. To the compound, about 100 ml of methanol was added and vacuum concentrated again to completely remove any remaining methylene chloride, after which drying under reduced pressure was conducted using a rotary pump. The amorphous material which foamed to a soft candy-like consistency, was beaten to result in TAS-6. The field goal was 78.5 g (at a yield of 70%). It was confirmed to be the specified substance using a 1H-NMR and a mass spectrometry

Reference： [1]Patent: US2004/244641,2004,A1 .Location in patent: Page 18

27
[ 1774-36-3 ]
[ 3699-01-2 ]
C₂₇H₂₅O₂S₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		Added to a one liter flask provided with a calcium chloride tube and a thermometer, were 32 g of phosphorus oxide and 288 g of methanesulfonic acid, stirred and heated for three hours to a temperature of 80 C.-90 C. After allowed to cool to room temperature, 78.7 g of <strong>[1774-36-3]bis(4-methoxyphenyl)sulfoxide</strong> and 60.1 g of 1-methyl-4-phenylsulfanyl-bemzene were added and stirred for three hours at ambient temperature. Added to a five liter conical beaker, was 55.2 g of potassium hexafluorophosphate and dissolved into three liters of purified water, after which the above reacted solution was added bit by bit while mechanically stirred to obtain a soft, white amorphous paste. After stirring, the supernatant liquid was decanted. Added to the residue, was 600 ml of methylene chloride, and following that a solution of 25 g of hexafluorophosphoric acid in 500 ml of purified water was added and dispersed for one hour. After siphoning off the water layer, the methylene chloride layer was vacuum concentrated to obtain the crude product, which was refined using an activated alumina column treatment, after which the solvent was vacuum concentrated to obtain a light brown, oily component. Added to the component, was hexane and suspended, after reprecipitation under vigorous mechanically stirring, TAS-11 was obtained, yielding 166.0 g at a yield of 94%. TAS-11 was confirmed to be the specified substance using a 1H-NMR and a mass spectrometry

Reference： [1]Patent: US2004/244641,2004,A1 .Location in patent: Page 18

28
methane sulfonic acid [ No CAS ]
[ 1774-36-3 ]
[ 91815-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; methoxybenzene;	EXAMPLE 2 A mixture of 192.22 g of methane sulfonic acid, 54.46 g of bis-(4-methoxyphenyl)sulfoxide and 500 ml of anisole was heated at 80 C. for 22 hours. The mixture was poured into 1000 g of ice water and extracted three times with 500-ml portions of ether. The aqueous phase was neutralized with 50 percent aqueous sodium hydroxide and extracted five times with 500-ml portions of chloroform. The combined chloroform phases were dried with magnesium sulfate and the chloroform was removed on a rotary evaporator to give 105.76 g of tris-(4-methoxyphenyl)sulfonium methane sulfonate with residual chloroform of solvation.

Reference： [1]Patent: US4451408,1984,A

29
[ 308290-53-1 ]
[ 1774-36-3 ]
ReOCH₃SC₆H₄CH₂SSO(C₆H₄OCH₃)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 4809 - 4814

30
[ 439098-82-5 ]
[ 1774-36-3 ]
[Pt(Me)(1,10-phenanthroline)(SO(p-MeOC₆H₄)2)][B(3,5-(CF₃)2C₆H₃)4] [ No CAS ]

Reference： [1]Inorganic Chemistry,2002,vol. 41,p. 2839 - 2847

31
[ 17084-13-8 ]
[ 1774-36-3 ]
[ 5331-28-2 ]
C₃₀H₃₁O₃S⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		To a one liter flask provided with a calcium chloride tube and a thermometer, 32 g of phosphorus oxide and 150 g of methanesulfonic acid were added, and stirred for three hours at an interior temperature of about 80 C. After being allowed to cool to room temperature, 54 g of <strong>[1774-36-3]bis(4-methoxyphenyl)sulfoxide</strong> and 46.8 g of 1-tert-butyl-4-phenoxybenzene were added and stirred for three hours while the flask was cooled with water. To a two liter conical beaker, 42 g of potassium hexafluorophosphate was added and mixed in one liter of iced water, and the above reacted solution was added a little at a time while mechanically stirred to obtain a soft, white amorphous material. After stirring, the supernatant liquid was removed by decanting. To the residue, one liter of methylene chloride was added. After water washing, the methylene chloride layer was vacuum concentrated to obtain a crude product, which was refined using an activated alumina column treatment, and the solvent was vacuum concentrated to obtain a light brown, oily component. To the component, about 100 ml of methanol was added and vacuum concentrated again to completely remove the methylene chloride, after which drying under reduced pressure was conducted using a rotary pump. The amorphous material which foamed to wheat gluten candy-like consistency was beaten to obtain TAS-4. The yield goal was 60.9 g (at a yield of 49%). It was determined to be the specified substance using a 1H-NMR and a mass spectrometry

Reference： [1]Patent: US2004/244641,2004,A1 .Location in patent: Page 17-18

32
[ 3988-99-6 ]
[ 1774-36-3 ]
bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 2.6 g (0.01 mol) of <strong>[1774-36-3]bis(4-methoxyphenyl) sulfoxide</strong>, 2.0 g (0.01 mol) of 2,2'-dithienyl sulfide and 5.1 g (0.05 mol) of acetic anhydride were charged and 3.8 g (0.04 mol) of methanesulfonic acid was added dropwise over 30 minutes while maintaining the inner temperature at 0 to 10C. After completion of the dropwise addition, stirring was conducted for 2 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 1.8 g (0.01 mol) of potassium hexafluorophosphate, 20 g of water and 20 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50C. After stirring at 40 to 50C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 5.9 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 4.2 g (0.007 mol) of bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium hexafluorophosphate as a pale yellow tar-like substance. As a result of the measurement by high performance liquid chromatograph, purity of the resultant bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium hexafluorophosphate was 98.7%. Also, the yield to 2,2'-dithienyl sulfide was 71%. It was confirmed by analytical results shown below that the resultant pale yellow tar-like substance is bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium hexafluorophosphate in which all R1b and R2b in the formula (B1) are 4-methoxyphenyl groups, all R3b to R5b are hydrogen atoms, and X- is a hexafluorophosphoric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 44.8%, H; 3.1%, F; 19.6%, O; 5.4%, S; 21.7% (theoretical value: C; 44.89%, H; 3.25%, F; 19.37%, O; 5.44%, S; 21.79%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) delta (ppm): 3.92(s, 6H), 7.10-7.14(m, 1H), 7.16-7.21(m, 5H), 7.40-7.42(m, 1H), 7.54-7.59(m, 4H), 7.60-7.63(m, 2H) Maximum absorption wavelength: 315.5 nm Molar extinction coefficient (365 nm): 0.2 × 103

Reference： [1]Patent: EP2218715,2010,A1 .Location in patent: Page/Page column 25-26

33
[ 3988-99-6 ]
[ 1774-36-3 ]
(thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bishexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of <strong>[1774-36-3]bis(4-methoxyphenyl) sulfoxide</strong>, 2.0 g (0.01 mol) of 2,2'-dithienyl sulfide and 10.2 g (0.1 mol) of acetic anhydride were charged and 7.7 g (0.08 mol) of methanesulfonic acid was added dropwise over 1 hour while maintaining the inner temperature at 0 to 10C. After completion of the dropwise addition, stirring was conducted for 2 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 3.7 g (0.02 mol) of potassium hexafluorophosphate, 40 g of water and 30 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50C. After stirring at 40 to 50C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 9.3 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 7.9 g (0.008 mol) of (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bishexafluorophosphate as a pale yellow solid. As a result of the measurement by high performance liquid chromatograph, purity of the resultant (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bishexafluorophosphate was 98.6%. Also, the yield to 2,2'-dithienyl sulfide was 80%. It was confirmed by analytical results shown below that the resultant pale yellow solid is (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bishexafluorophosphate in which all R1a, R2a, R3a and R4a in the formula (A1) are 4-methoxyphenyl groups and X- is a hexafluorophosphoric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 44.1%, H; 3.3%, F; 23.5%, O; 6.4%, S; 16.6% (theoretical value: C; 44.17%, H; 3.29%, F; 23.29%, O; 6.54%, S; 16.38%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) delta (ppm): 3.93(s, 12H), 7.18-7.24(m, 8H), 7.45(d, 2H), 7.59(d, 2H), 7.64-7.69(m, 8H) Molar extinction coefficient (365 nm); 1.2 × 103

Reference： [1]Patent: EP2218715,2010,A1 .Location in patent: Page/Page column 21

34
[ 3988-99-6 ]
[ 1774-36-3 ]
lithium tetrakis(pentafluorophenyl)borate ethyl etherate [ No CAS ]
bis(4-methoxyphenyl)[5-(thiophene-2-ylthio)thiophene-2-yl]sulfonium tetrakis(pentafluorophenyl)borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 2.6 g (0.01 mol) of <strong>[1774-36-3]bis(4-methoxyphenyl) sulfoxide</strong>, 2.0 g (0.01 mol) of 2,2'-dithienyl sulfide and 5.1 g (0.05 mol) of acetic anhydride were charged and 3.8 g (0.04 mol) of methanesulfonic acid was added dropwise over 30 minutes while maintaining the inner temperature at 0 to 10C. After completion of the dropwise addition, stirring was conducted for 2 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 9.4 g (0.01 mol) of lithium tetrakis(pentafluorophenyl)borate (73 wt%-diethylether complex), 50 g of water and 30 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50C. After stirring at 40 to 50C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 10.9 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 7.6 g (0.007 mol) of bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium tetrakis(pentafluorophenyl)borate as a pale yellow solid. As a result of the measurement by high performance liquid chromatograph, purity of the resultant bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium tetrakis(pentafluorophenyl)borate was 98.8%. Also, the yield to 2,2'-dithienyl sulfide was 68%. It was confirmed by analytical results shown below that the resultant pale yellow solid is bis(4-methoxyphenyl)[5-(thiophen-2-ylthio)-thiophen-2-yl]sulfonium tetrakis(pentafluorophenyl)borate in which all R1b and R2b in the formula (B1) are 4-methoxyphenyl groups, all R3b to R5b are hydrogen atoms, and X- is a tetrakis(pentafluorophenyl)boric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 49.3%, H; 1.7%, F; 33.6%, 2.9%, S; 11.3% (theoretical value: C; 49.21%, H; 1.71%, F; 33.84%, O; 2.85%, S; 11.42%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) delta (ppm): 3.90(s, 6H), 7.10-7.13(m, 1H), 7.13-7.18(m, 5H), 7.39-7.42(m, 1H), 7.46-7.51(m, 5H), 7.60-7.62(m, 1H) Molar extinction coefficient (365 nm): 0.3 × 102

Reference： [1]Patent: EP2218715,2010,A1 .Location in patent: Page/Page column 27

35
[ 3988-99-6 ]
[ 1774-36-3 ]
lithium tetrakis(pentafluorophenyl)borate ethyl etherate [ No CAS ]
(thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bis[tetrakis(pentafluorophenyl)borate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of <strong>[1774-36-3]bis(4-methoxyphenyl) sulfoxide</strong>, 2.0 g (0.01 mol) of 2,2'-dithienyl sulfide and 10.2 g (0.1 mol) of acetic anhydride were charged and 7.7 g (0.08 mol) of methanesulfonic acid was added dropwise over 1 hour while maintaining the inner temperature at 0 to 10C. After completion of the dropwise addition, stirring was conducted for 2 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 300 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 18.8 g (0.02 mol) of lithium tetrakis(pentafluorophenyl)borate (73 wt%-diethylether complex), 100 g of water and 50 g of monochlorobenzene, were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50C. After stirring at 40 to 50C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 21.0 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 15.3 g (0.007 mol) of (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bis[tetrakis(pentafluorophenyl)borate] as a pale yellow solid. As a result of the measurement by high performance liquid chromatograph, purity of the resultant (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bis[tetrakis(pentafluorophenyl)borate] was 98.5%. Also, the yield to 2,2'-dithienyl sulfide was 75%. It was confirmed by analytical results shown below that the resultant pale yellow solid is (thiodi-5,2-thienylene)bis[bis(4-methoxyphenyl)sulfonium] bis[tetrakis(pentafluorophenyl)borate] in which all R1a, R2a, R3a and R4a in the formula (A1) are 4-methoxyphenyl groups and X- is a tetrakis(pentafluorophenyl)boric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 49.4%, H; 1.5%, F; 37.1%, O; 3.0%, S; 8.0% (theoretical value: C; 49.29%, H; 1.58%, F; 37.12%, O; 3.13%, S; 7.83%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) delta (ppm): 3.90(s, 12H), 7.11-7.16(m, 8H), 7.33(d, 2H), 7.42(d, 2H), 7.48-7.53(m, 8H) Molar extinction coefficient (365 nm); 0.9 × 103

Reference： [1]Patent: EP2218715,2010,A1 .Location in patent: Page/Page column 23

36
[ 16718-12-0 ]
[ 1774-36-3 ]
bis(4-methoxyphenyl)-(5-phenylthio-thiophen-2-yl)sulfonium hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 2.6 g (0.01 mol) of <strong>[1774-36-3]bis(4-methoxyphenyl) sulfoxide</strong>, 1.9 g (0.01 mol) of 2-(phenylthio)thiophene and 5.1 g (0.05 mol) of acetic anhydride were charged and 4.8 g (0.05 mol) of methanesulfonic acid was added dropwise over 1 hour while maintaining the inner temperature at 0 to 10C. After completion of the dropwise addition, stirring was conducted for 3 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 1.8 g (0.01 mol) of potassium hexafluorophosphate, 30 g of water and 20 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50C. After stirring at 40 to 50C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 5.5 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 4.8 g (0.008 mol) of bis(4-methoxyphenyl)(5-phenylthio-thiophen-2-yl)sulfonium hexafluorophosphate as a pale yellow tar-like substance. As a result of the measurement by high performance liquid chromatograph, purity of the resultant bis(4-methoxyphenyl)(5-phenylthio-thiophen-2-yl)sulfonium hexafluorophosphate was 98.8%. Also, the yield to 2-(phenylthio)thiophene was 82%. It was confirmed by analytical results shown below that the resultant pale yellow tar-like substance is bis(4-methoxyphenyl)(5-phenylthio-thiophen-2-yl)sulfonium hexafluorophosphate in which all R1c and R2c in the formula (C1) are 4-methoxyphenyl groups, all R3c to R7c are hydrogen atoms, and X- is a hexafluorophosphoric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 49.3%, H; 3.7%, F; 19.7%, O; 5.4%, S; 16.8% (theoretical value: C; 49.48%, H; 3.63%, F; 19.57%, O; 5.49%, S; 16.51%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) delta (ppm): 3.91(s, 6H), 7.16-7.22 (m, 4H), 7.25(d, 1H), 7.39-7.44(m, 3H), 7.46-7.51(m, 2H), 7.56-7.62(m, 4H), 7.65(d, 1H) Molar extinction coefficient (365 nm): 1.3 × 103

Reference： [1]Patent: EP2218715,2010,A1 .Location in patent: Page/Page column 29-30

37
isopropylmagnesium chloride lithium chloride complex [ No CAS ]
[ 1774-36-3 ]
[ 138723-23-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 3136 - 3140

38
[ 1774-36-3 ]
[ 3536-97-8 ]
[ 7205-71-2 ]
[ 7205-71-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 3136 - 3140

39
[ 7719-09-7 ]
[ 100-66-3 ]
[ 1774-36-3 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 2151 - 2153

40
[ 1774-36-3 ]
[ 557-18-6 ]
[ 128092-50-2 ]
(-)-(S)-ethyl (4-methoxyphenyl) sulfoxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 2518 - 2530

41
[ 1774-36-3 ]
[ 557-18-6 ]
[ 7205-68-7 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910

42
[ 1774-36-3 ]
[ 1191-47-5 ]
[ 78597-97-4 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910

43
[ 1774-36-3 ]
[ 1191-47-5 ]
(S)-(-)-butyl (4-methoxyphenyl)sulfoxide [ No CAS ]
(R)-(-)-butyl (4-methoxyphenyl)sulfoxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910

44
[ 1774-36-3 ]
[ 2892-94-6 ]
isobutyl (4-methoxyphenyl)sulfoxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910

45
[ 1774-36-3 ]
[ 2892-94-6 ]
(S)-(-)-isobutyl (4-methoxyphenyl)sulfoxide [ No CAS ]
(R)-(-)-isobutyl (4-methoxyphenyl)sulfoxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 897 - 910

46
[ 1774-36-3 ]
[ 536-74-3 ]
2-(5-methoxy-2-((4-methoxyphenyl)thio)phenyl)-1-phenylethan-1-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 4727 - 4732

47
[ 1774-36-3 ]
[ 217813-00-8 ]
(2-(3,4-difluorophenoxy)-4,5-difluorophenyl)bis(4-methoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 838 - 841

48
[ 1774-36-3 ]
[ 88284-48-4 ]
bis(4-methoxyphenyl)(2-phenoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With cesium fluoride; In acetonitrile; at 25℃; for 9h;Inert atmosphere;	At room temperature, in 25mL reaction tube vacuum, nitrogen three times, under nitrogen protection by adding cesium fluoride(0.3 mmol) and acetonitrile (3 mL) were added followed by 78.7 mg (0.3 mmol) of bis-4-methoxyphenylsulfoxide and finally addedBenzynylamine 89.5 mg (0.3 mmol) was added and the reaction was carried out at 25 C. The reaction process was followed by thin layer chromatographyProduct ratio of 15: 1 dichloromethane / methanol, the reaction time of 7h, after the end of the reaction, the reaction material through the column chromatography short column filterCesium fluoride was dropped and concentrated in vacuo and isolated by column chromatography to give the desired product in a yield of 96%

Reference： [1]Organic Letters,2017,vol. 19,p. 838 - 841
[2]Patent: CN106892848,2017,A .Location in patent: Paragraph 0056; 0057; 0058; 0059

49
lithium tetrakis[pentafluorophenyl]borate ethyl etherate [ No CAS ]
[ 139-66-2 ]
[ 1774-36-3 ]
bis(4-methoxyphenyl)(4-phenylthiophenyl)sulfonium tetrakis(pentafluorophenyl)borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of bis (4-methoxyphenyl)sulfoxide, 3.9 g (0.02 mol) of diphenyl sulfide, methanesulfonic acid 5.8 g (0.06 mol) and 0.03 g (0.0002 mol) of aluminum chloride were charged, while maintaining the internal temperature at 5 to 15 C, 6.1 g (0.06 mol) of concentrated sulfuric acid was added dropwise over 1 hour. After completion of the dropwise addition, The reaction solution of the condensation reaction product was obtained by stirring for 2 hours while maintaining the same temperature and further stirring at 20 to 25 C. for 1 hour. The reaction rate of bis (4-methoxyphenyl) sulfoxide was 99.5%. Into a 300 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, Tetrakis (pentafluorophenyl) borate lithium (73 wt% - diethyl ether complex) 18.8 g (0.02 mol), 100 g of water and 50 g of monochlorobenzene were charged, while maintaining the internal temperature at 30 to 50 C., the whole amount of the reaction solution was added dropwise over 30 minutes. Further, after stirring at 40 Cto 50 C. for 30 minutes, the monochlorobenzene layer was separated. then, after washing the obtained monochlorobenzene layer with 50 g of water, Monochlorobenzene was distilled off to obtain 21.1 g of a pale yellow concentrate. The yield of bis (4-methoxyphenyl) (4-phenylthiophenyl) sulfonium tetrakispentafluorophenyl borate relative to bis (4-methoxyphenyl) sulfoxide was 95.0% . The purity by HPLC analysis was 99.1%.

Reference： [1]Patent: JP6112813,2017,B2 .Location in patent: Paragraph 0099-0100

50
[ 3988-99-6 ]
lithium tetrakis[pentafluorophenyl]borate ethyl etherate [ No CAS ]
[ 1774-36-3 ]
bis(4-methoxyphenyl)[5-(thiophene-2-ylthio)thiophene-2-yl]sulfonium tetrakis(pentafluorophenyl)borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.2%		In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of bis (4-methoxyphenyl) sulfoxide, 4.0 g (0.02 mol) of 2,2'-dithienyl sulfide, 9.6 g (0.16 mol) of acetic acid and 0.03 g (0.0002 mol) of aluminum chloride were charged, while maintaining the internal temperature at 5 to 15 C, 13.7 g (0.14 mol) of concentrated sulfuric acid was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred for 4 hours while maintaining the same temperature, By further stirring at 20 to 25 C. for 2 hours, to obtain a reaction solution of the condensation reaction product. The reaction rate of bis (4-methoxyphenyl) sulfoxide was 96.5%. Into a 300 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 18.8 g (0.02 mol) of lithium tetrakis(pentafluorophenyl)borate (73 wt% -diethyl ether complex), 100 g of water and 50 g of monochlorobenzene were charged, and while maintaining the internal temperature at 30 Cto 50 C. over 30 minutes. The whole amount of the reaction solution was added dropwise. Further, after stirring at 40 to 50 C. for 30 minutes, the monochlorobenzene layer was separated. Next, after washing the obtained monochlorobenzene layer with 50 g of water, monochlorobenzene was distilled off to obtain 21.6 g of a pale yellow concentrate. The yield of bis(4-methoxyphenyl)[5- (thiophene-2-ylthio)-thiophene-2-yl] sulfonium tetrakispentafluorophenyl borate to <strong>[1774-36-3]bis(4-methoxyphenyl)sulfoxide</strong> was 96.2%, HPLC The analytical purity was 96.1%.

Reference： [1]Patent: JP6112813,2017,B2 .Location in patent: Paragraph 0107-0108

51
[ 1774-36-3 ]
[ 615567-09-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

52
[ 1774-36-3 ]
[ 615567-09-4 ]
CF₃O₃S^(1-)*C₂₀H₁₈⁽²⁾HO₂S⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

53
[ 1774-36-3 ]
(3,4-dimethylphenyl)bis(4-methoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

54
[ 1774-36-3 ]
benzo[d][1,3]dioxol-5-ylbis(4-methoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

55
[ 1774-36-3 ]
(3-methoxyphenyl)bis(4-methoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

56
[ 1774-36-3 ]
(3-bromophenyl)bis(4-methoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7181 - 7189

57
[ 1774-36-3 ]
[ 217813-03-1 ]
3-methoxy-2-(4-methoxyphenylthio)phenyl 4-methoxyphenyl ether [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5521 - 5524

58
[ 1774-36-3 ]
[ 73183-34-3 ]
[ 171364-79-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With chloro(2-dicyclohexylphosphino-2?,6?-dimethoxy-1,1?-biphenyl)(2?-amino-1,1?-biphenyl-2-yl) palladium(II); lithium hexamethyldisilazane; In tetrahydrofuran; at 80℃; for 40h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with diphenyl sulfoxide (1a) (41 mg, 0.20mmol), SPhos Pd G2 (7.2 mg, 0.010 mmol), B 2 pin 2 (0.20 g, 0.80 mmol),and LiN(SiMe 3 ) 2 (0.20 g, 1.2 mmol). THF (0.80 mL) was added to thetube and the resulting mixture was stirred at 80 C for 20 h. After thereaction was complete, saturated aqueous NH 4 Cl (2 mL) was addedand the resulting biphasic mixture was extracted with Et 2 O (5 × 5mL). The combined organic layer was dried over Na 2 SO 4 , passedthrough a pad of silica gel, and concentrated under reduced pressure.The residue was purified by preparative TLC (hexane/EtOAc = 10:1) toprovide (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (2a)(54 mg, 0.26 mmol, 66%) as a colorless oil. All the resonances in the 1 Hand 13 C NMR spectra were consistent with the reported data. 12a

Reference： [1]Synthesis,2017,vol. 49,p. 4769 - 4774

59
[ 629-05-0 ]
[ 1774-36-3 ]
[ 197635-86-2 ]

Yield	Reaction Conditions	Operation in experiment
14%Spectr.	With ([1,3-bis(2,6-diisopropylphenyl)imidazolidene]-(3-chloropyridine)palladium(II) dichloride); lithium tert-butoxide; In tetrahydrofuran; at 70℃; for 6h;Schlenk technique; Inert atmosphere;	General procedure: The reaction of 1a with 2a is representative. An oven-dried Schlenk tube was charged withdiphenyl sulfoxide (1a, 61 mg, 0.30 mmol), 1-dodecyne (2a, 60 mg, 0.36 mmol), Pd-PEPPSISIPr(5.1 mg, 0.0075 mmol), LiOtBu (36 mg, 0.45 mmol), and THF (1.5 mL). The resultingmixture was stirred at 70 C for 6 h. The reaction was quenched with saturated aqueous NH4Cl (0.10 mL), and the resulting mixture was passed through pads of anhydrous Na2SO4, activated alumina, and silica gel with Et2O as an eluent. The ethereal solution wasconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography with an eluent (hexane/toluene = 25/1) to provide 3aa as a colorless oil (68mg, 0.28 mmol, 93% yield).

Reference： [1]Synlett,2017,vol. 28,p. 2561 - 2564

60
[ 1774-36-3 ]
[ 106-49-0 ]
[ 39253-43-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1134 - 1137

61
[ 1774-36-3 ]
[ 1875-48-5 ]
C₂₂H₁₈N₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		General procedure: Sc(OTf)3 (0.075 mmol) was added to the suspension of IBX (0.75 mmol) and PhthNH2 (0.8mmol) in EA (4 mL) under nitrogen atmosphere. After stirring 10 min at rt, sulfoxide (1 mmol) was added. The RM was strirred at reflux for 3 h, allowed to reach rt. IBX (0.75 mmol) and PhthNH2 (0.8 mmol) were added to RM and strirred at reflux for 5h, allowed to reach rt. IBX(0.75 mmol) and PhthNH2 (0.8 mmol) were added to RM and strirred at reflux for 13h, allowed to reach rt. The RM was quenched with saturated solution of Na2CO3. The separated organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using Hexane: EA (2.5:1) to afford sulfoximine.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 946 - 953

62
[ 1774-36-3 ]
ethyl (R)-6-methoxy-1-(4-methoxyphenyl)-3-methyl-1λ⁴-benzo[e][1,2]thiazine-4-carboxylate 1-oxide [ No CAS ]
ethyl 6-methoxy-1-(4-methoxyphenyl)-3-methyl-1λ⁴-benzo[e][1,2]thiazine-4-carboxylate 1-oxide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 15539 - 15543
Angew. Chem.,2018,vol. 130,p. 15765 - 15769,5

63
[ 1774-36-3 ]
[ 55440-60-3 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 15539 - 15543
Angew. Chem.,2018,vol. 130,p. 15765 - 15769,5
[2]Journal of Organic Chemistry,2019,vol. 84,p. 8248 - 8255

64
[ 459-64-3 ]
[ 1774-36-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3048 - 3055

65
[ 696-63-9 ]
1-(methylsulfonyl)-2-(4-methoxyphenyl)diazene [ No CAS ]
[ 1774-36-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	In water; acetonitrile; at 25℃; for 16h;Irradiation;	In a 15 mL reaction tube,P-methoxyphenylazomethylsulfone 1a (0.6 mmol) was added in sequence.P-methoxythiophenol 2e (0.2 mmol), 1 mL of acetonitrile and 1 mL of water,Mix evenly, then under the illumination of 3W blue LED light,The reaction was stirred at 25 C for 16 h.After the reaction was completed by TLC, the mixture was extracted with ethyl acetate.3 mL each time, extract 3 times, combine the extracts, and the extract is dried over anhydrous sodium sulfate.The extract was concentrated under reduced pressure in vacuo (0.08 Mpa) to dryness to afford crude material.Then rinse with a mixed eluent of 5:1 by volume of petroleum ether and ethyl acetate.Flash column chromatography on silica gel to obtain the sulfoxide product of this example.It was 42.5 mg of a yellow oily solid, yield 81%.

Reference： [1]Green Chemistry,2019,vol. 21,p. 1609 - 1613
[2]Patent: CN109810030,2019,A .Location in patent: Paragraph 0031; 0032

66
[ 1774-36-3 ]
6-methoxy-1-(4-methoxyphenyl)-3-phenylbenzo[e][1,2]thiazine1-oxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 8248 - 8255

67
[ 1774-36-3 ]
(E)-[(1,3-bis(2,6-bis-(diisopropylphenyl)imidazol-2-ylidene))AuC(H)C(H)C(4-C₆H₄OMe)₂]⁺ OTf^- [ No CAS ]
{(1,3-bis(2,6-bis-(diisopropylphenyl)imidazol-2-ylidene))Au[η¹-C(H)(O-S(4-C₆H₄OMe)₂)-C(H)=C(4-C₆H₄OMe)₂]⁺ OTf^– [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 13745 - 13748

68
[ 1774-36-3 ]
[ 144272-12-8 ]
1-(5-methoxy-2-((4-methoxyphenyl)thio)phenyl)-3-(triisopropylsilyl)propan-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 17303 - 17306
Angew. Chem.,2019,vol. 131,p. 17463 - 17467,5

69
[ 1774-36-3 ]
[ 5720-05-8 ]
[ 53040-92-9 ]