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Chemical Structure| 14752-66-0 Chemical Structure| 14752-66-0
Chemical Structure| 14752-66-0

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CAS No.: 14752-66-0

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Product Details of [ 14752-66-0 ]

CAS No. :14752-66-0
Formula : C6H4ClNaO2S
M.W : 198.60
SMILES Code : O=S(C1=CC=C(Cl)C=C1)[O-].[Na+]
MDL No. :MFCD00035602
InChI Key :JFXAUUFCZJYLJF-UHFFFAOYSA-M
Pubchem ID :23664783

Safety of [ 14752-66-0 ]

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

Calculated chemistry of [ 14752-66-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 38.77
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

59.34 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-4.25
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.75
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.44
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.87
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.52

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.51
Solubility 0.612 mg/ml ; 0.00308 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.61
Solubility 0.484 mg/ml ; 0.00244 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.45
Solubility 0.7 mg/ml ; 0.00352 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.27 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.61

Application In Synthesis [ 14752-66-0 ]

* 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 [ 14752-66-0 ]

[ 14752-66-0 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 14752-66-0 ]
  • [ 96-34-4 ]
  • [ 15446-25-0 ]
YieldReaction ConditionsOperation in experiment
98% In N,N-dimethyl-formamide; at 45 - 115℃; for 3h; A solution of 108.53 g (1 mol) of methyl ester ofmonochloroacetic acid (4) in 200 mL of DMF was addedto a suspension of 198.6 g (1 mol) of <strong>[14752-66-0]sodium 4-chlorophenylsulfinate</strong> (prepared by reacting 4-chlorophenylsulfochloridewith sodium sulfi te in 500 mL of DMF)heated to 45C. The reaction mixture was heated withstirring to 115C for 3 h. After cooling, it was pouredinto 3 L of cold water and held in a refrigerator for 12 h.The precipitate was fi ltered off, recrystallized from chloroform-hexane, and dried over P2O5. 233.7 g (98%) ofester 5 was obtained, mp 81-82C. 1 NMR spectrum, δ, ppm (D3OD): 7.40-7.31 m (4, 64), 4.05 s (2,2), 3.29 s (3, 3). IR spectrum, ν, cm-1:1735 (), 1150, 1330 (SO2). Found, %: C 43.80,H 3.45, Cl 14.11, S 13.12. C9H9ClO4S. Calculated, %:C 43.46, H 3.66, Cl 14.25, S 12.89.
  • 2
  • [ 14752-66-0 ]
  • [ 79-11-8 ]
  • [ 3405-89-8 ]
  • [ 98-57-7 ]
YieldReaction ConditionsOperation in experiment
92%; 7% With sodium hydroxide; In water; at 100℃; for 1h;pH 10.0;Green chemistry; (b) Sodium 4-chlorophenylsulfi nate [9.93 g(0.05 mol)] and monochloroacetic acid [4.72 g(0.05 mol)] were dissolved in 20 mL of water, adjustedto pH 10 with a NaOH solution, and boiled in a waterbath for 1 h. The reaction mixture was cooled, and extractedwith benzene (2 × 30 mL). From the benzenesolution, after distilling off the solvent, 0.67 g (7%)of sulfone (3), i.e., 4-lC6H4SO2CH3 was obtained,mp 93-95C. Found, %: 44.30, 3.58, Cl 18.41,S 16.67. 77Cl2S. Calculated (%): 44.10, 3.71,Cl 18.59, S 16.82The aqueous layer was acidifi ed with HCl untilneutral and held at 5C for 12 h. The precipitate wasrecrystallized (chloroform-hexane, 1 : 2) and dried invacuo over P2O5. 10.78 g (92%) of acid (1) was obtained,mp 120-122C.
  • 3
  • [ 14752-66-0 ]
  • [ 824-98-6 ]
  • 4-chloro-1-[(3-methoxyphenylsulfonyl)methyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Example 82: 1-(4-Chlorophenylsulfonylmethyl)-3-methoxybenzene A dimethoxyethane (10 ml) suspension of <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (210 mg, 1.06 mmol) and 3-methoxybenzyl chloride (154 μl, 1.06 mmol) was stirred at 70C for 16 hours.. After cooling to room temperature, butanol (2 ml) and tetrabutylammonium bromide (45 mg) were added and the resulting mixture was stirred further at 70C for 16 hours.. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure.. ethyl acetate was added to the residue.. The mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=5:1) elude was concentrated under reduced pressure, whereby the title compound (216 mg, 69%) was obtained as a white solid. IR (ATR) ν: 3064, 2979, 2842, 1598, 1488, 1469, 1434, 1392, 1313, 1268, 1176, 1130, 1085, 1033, 1012, 941, 879, 823, 792, 765, 742, 692, 620, 574, 528, 455 cm-1.1H-NMR (400MHz, CDCl3) δ: 3.74(3H,s), 4.27(2H,s), 6.59-6.68(2H,m), 6.82-6.90(1H,m), 7.17(1H,t,J=7.8Hz), 7.42(2H,d,J=8.6Hz), 7.56(2H,d,J=8.6Hz). MS (m/z): 297 (M++H).
  • 4
  • [ 14752-66-0 ]
  • [ 85482-13-9 ]
  • C13H9Cl3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane; at 70℃; for 24h; Example 71: 1,4-Dichloro-2-[1-[(4-chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]benzene sodium 4-chlorobenzenesulfinate (38 mg, 0.192 mmol) and <strong>[85482-13-9]2,5-dichlorobenzyl bromide</strong> (46 mg, 0.192 mmol) were added to dimethoxyethane (5 ml).. The resulting mixture was stirred at 70C for 24 hours.. After cooling to room temperature, the reaction mixture was subjected to a short column (silica gel) and the fraction eluted with diethyl ether was concentrated under reduced pressure.. The residue thus obtained was dissolved in toluene (5 ml).. To the resulting solution were added the 4-(methylsulfonyl)-1-butanol (58 mg, 0.381 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (89 mg, 0.370 mmol), followed by heating under reflux for 23 hours under an argon atmosphere.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue was subjected to medium-pressure chromatography on a silica gel column.. From the fraction eluted with hexane:ethyl acetate (=1:1), the title compound (32 mg, 35%) was obtained as a colorless oil. IR (ATR) nu: 2933, 2869, 1581, 1465, 1394, 1313, 1278, 1191, 1133, 1083, 1039, 1012, 962, 887, 821, 752, 713, 630, 588, 532, 464 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.33-1.50(2H,m), 1.80-1.96(2H,m), 2.09-2.21(1H,m), 2.48-2.59(1H,m), 2.88(3H,s), 2.90-2.99(2H,t,J=11.0,4.2Hz), 4.79(1H,dd,J=11.0,4.2 Hz), 7.15(1H,d,J=8.6Hz), 7.20-7.29(1H,m), 7.34-7.40(2H,m), 7.46-7.52(2H,m), 7.63(1H,d,J=2.5Hz). MS (m/z): 469, 471 (M++H). HRMS (FAB) for C18H20O4Cl3S2 (M++H) Calculated: 468.9869 Found: 468.9907
  • 5
  • [ 14752-66-0 ]
  • [ 1822-51-1 ]
  • [ 558462-62-7 ]
YieldReaction ConditionsOperation in experiment
62% With potassium acetate; In propan-1-ol; at 70℃; for 8h; Example 119: 4-(4-Chlorophenylsulfonylmethyl)pyridine Under heating, a 1-propanol (50 ml) solution of 4-chloromethylpyridine hydrochloride (1.26 g, 7.65 mmol), <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (1.52 g, 7.65 mmol) and potassium acetate (1.50 g, 15.3 mmol) was stirred at 70C for 8 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue was filtered through a short column (silica gel, ethyl acetate) and the elude was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=2:3) elude was concentrated under reduced pressure, whereby the title compound (1.26 g, 62%) was obtained as a white solid.1H-NMR (400MHz, CDCl3) δ: 4.29(2H,s), 7.06(2H,d,J=6.1Hz), 7.47(2H,d,J=8.8Hz), 7.59(2H,d,J=8.5Hz), 8.57(2H,d,J=6.1Hz). MS (m/z): 268 (M++H).
62% With potassium acetate; In propan-1-ol; at 70℃; for 8h; A 1-propanol (50 ml) solution of 4-chloromethylpyridine hydrochloride (1.26 g, 7.65 mmol), <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (1.52 g, 7.65 mmol) and potassium acetate (1.50 g, 15.3 mmol) was stirred under heating at 70C for 8 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue thus obtained was caused to pass through a short column (silica gel, ethyl acetate) and the eluate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, and the fraction obtained from the hexane:ethyl acetate (=2:3) eluate was concentrated under reduced pressure to give the title compound (1.26 g, 62%) as a white solid. 1H-NMR(400MHz, CDCl3) δ: 4.29(2H,s), 7.06(2H,d,J=6.1Hz), 7.47(2H,d,J=8.8Hz), 7.59(2H,d,J=8.5Hz), 8.57(2H,d,J=6.1Hz). MS (m/z) : 268 (M++H).
With potassium acetate; In butan-1-ol; at 70℃; for 5h; Example 74: 4-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]pyridine <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (207 mg, 1.04 mmol), 3-chloromethylpyridine hydrochloride (171 mg, 1.04 mmol) and potassium acetate (204 mg, 2.08 mmol) were added to n-butanol (5 ml).. The resulting mixture was stirred at 70C for 5 hours.. After cooling to room temperature, the solvent was concentrated under reduced pressure.. To the residue was added ethyl acetate and from the resulting mixture, the insoluble matter was filtered off.. The filtrate was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column and the from the fraction eluted with hexane:ethyl acetate (=2:3), a white solid (117 mg) was obtained. Then, a toluene (10 ml) solution of the resulting solid (52 mg), the 4-(methylsulfonyl)-1-butanol (90 mg, 0.592 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (140 mg, 0.582 mmol) was heated under reflux for 2 days under an argon atmosphere..
  • 6
  • [ 14752-66-0 ]
  • [ 939-26-4 ]
  • 2-(((4-chlorophenyl)sulfonyl)methyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% A mixture of THF, K2CO3 (0.77 g 0 006 mol) and sodium 4-chloro- benzenesulfinate(0.75 g, 3.7 mmol) was stirred for 15 en blanket and cooled to 0-5 C. <n="19"/>Naphth-2-ylmethylbromide (0.81 g, 3.7 mmol) was added to the reaction mixture. The mixture was stirred at 65 - 67 C for two hours and the solvent was removed by distillation. The resultant solid residue was recrystallized from isopropanol to give the title product, 0.30g, 51% yield, 99% purity by HPLC
In 1,2-dimethoxyethane; at 70℃; for 5h; Example 67: 2-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]naphthalene <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (211 mg, 1.06 mmol) and 2-bromomethylnaphthalene (235 mg, 1.06 mmol) were added to dimethoxyethane (5 ml).. The resulting mixture was stirred at 70C for 5 hours.. After cooling to room temperature, the solvent was concentrated under reduced pressure.. The residue was added with ethyl acetate and from the resulting mixture, the insoluble matter was filtered off.. The residue obtained by concentrating the filtrate under reduced pressure was washed with hexane to yield a white powder (90 mg). Then, a toluene (10 ml) solution of the resulting white powder (60 mg), the 4-(methylsulfonyl)-1-butanol (59 mg, 0.388 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (91 mg, 0.379 mmol) was heated under reflux for 21 hours under an argon atmosphere.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue was subjected to medium-pressure chromatography on a silica gel column, whereby from the fraction eluted with hexane:ethyl acetate(=2:3), the title compound was obtained as a white solid (62 mg). Melting point: 146.0-147.0C. IR (ATR) ν: 2931, 2861, 1581, 1508, 1473, 1457, 1392, 1359, 1309, 1274, 1191, 1147, 1126, 1081, 1010, 968, 902, 869, 819, 752, 734, 703, 646, 624, 566, 522, 472, 453 cm-1.1H-NMR (400MHz, CDCl3) δ: 1.34-1.51(2H,m), 1.78-1.99(2H,m), 2.25-2.40(1H,m), 2.50-2.62(1H,m), 2.84(3H,s), 2.89-3.03(2H,m), 4.19(1H,dd,J=11.2,3.9Hz), 7.18-7.36(4H,m), 7.39-7.61(4H,m), 7.69-7.90(3H,m). MS (m/z): 451 (M++H). Elemental Analysis for C22H23ClO4S2 Calculated: C 58.59%; H 5.14%; Cl 7.86%; S 14.22%. Found: C 58.46%; H 5.03%; Cl 7.94%; S 14.33%.
  • 7
  • [ 866782-59-4 ]
  • [ 14752-66-0 ]
  • [ 933792-11-1 ]
YieldReaction ConditionsOperation in experiment
33% With potassium carbonate; N,N`-dimethylethylenediamine;copper(l) iodide; In dimethyl sulfoxide; at 100℃; for 8h; Description 3 3-[(4-Chlorophenyl)sulfonyl]-8-fluoroquinoline (D3) EPO <DP n="19"/>A mixture of 8-fluoro-3-iodoquinoline (D1 ) (750 mg, 2.75 mmol), sodium 4- chlorobenzenesulfinate (1.1 g, 5.5 mmol), copper (I) iodide ( 52 mg, 0.275 mmol) and potassium carbonate (380 mg, 2.75 mmol) was treated with λ/./V-di methyl- 1 ,2- ethanediamine (49 mg, 0.55 mmol) and anhydrous dimethylsulphoxide (4 ml). The mixture was stirred at 1000C under argon for 8 hr, and cooled to 200C. The reaction mixture was diluted with water (60 ml) and extracted with ethyl acetate (3 x 40 ml). The organic extracts were combined, washed with water (60 ml) and brine (60 ml), dried over magnesium sulphate, and evaporated to dryness. The residue was dissolved in a 1 :1 mixture of dimethylsulphoxide and acetonitrile and purified by mass-directed auto- preparative chromatography using 10 minute gradients containing water and between 50% and 99% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to yield the title compound as a white solid (295 mg, 33%). δH (CDCI3, 400MHz) 7.51-7.69 (4H, m), 7.79 (1 H, d, J = 8 Hz), 7.96-7.99 (2H, m), 8.84 (1 H, d, J = 2 Hz), 9.30 (1 H, d, J = 2 Hz) Mass spectrum: C15H9CIFNO2S requires 321 ; found 322 (MH+)
33% With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; In dimethyl sulfoxide; at 100℃; for 8h; A mixture of 8-fluoro-3-iodoquinoline (750 mg, 2.75 mmol), sodium 4- chlorobenzenesulfinate (1.1 g, 5.5 mmol), copper (I) iodide ( 52 mg, 0.275 mmol) and potassium carbonate (380 mg, 2.75 mmol) was treated with λ^, λ^-dimethyl-l,2-ethanediamine (49 mg, 0.55 mmol) and anhydrous dimethylsulphoxide (4 ml). The mixture was stirred at 1000C under argon for 8 hr, and cooled to 200C. The reaction mixture was diluted with water <n="215"/>(60 ml) and extracted with ethyl acetate (3 x 40 ml). The organic extracts were combined, washed with water (60 ml) and brine (60 ml), dried over magnesium sulphate, and evaporated to dryness. The residue was dissolved in a 1 :1 mixture of dimethylsulphoxide and acetonitrile and purified by mass-directed auto -preparative chromatography using 10 minute gradients containing water and between 50% and 99% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to yield the title compound as a white solid (295 mg,δH (CDCl3, 400MHz) 7.51-7.69 (4H, m), 7.79 (IH, d, J = 8 Hz), 7.96-7.99 (2H, m), 8.84 (IH, d, J = 2 Hz), 9.30 (IH, d, J = 2 Hz)Mass spectrum: C15H9ClFNO2S requires 321; found 322 (MH+)
  • 8
  • [ 273-53-0 ]
  • [ 14752-66-0 ]
  • [ 1141-35-1 ]
YieldReaction ConditionsOperation in experiment
83% General procedure: Under nitrogen atmosphere, a sealable reaction tube equipped with a magnetic stirrer bar was charged with azole (0.50 mmol), sodium arylsulfinate (1.0 mmol), Pd(OAc)2 (0.025 mmol), Cu(OAc)2 (1.0 mmol), CF3COOH (0.50 mmol), and dimethylglycol (2.0 mL). The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel placed in an oil bath at 120 C for 24 h. After the reaction was completed, it was cooled to room temperature and the mixture was treated with K2CO3 solution (1.0 mol/L, 3.0 mL), then extracted with ethyl acetate. The resulting solution was dried by Na2SO4 then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate=12:1, v/v) to give the desired product.
  • 9
  • [ 14135-38-7 ]
  • [ 14752-66-0 ]
  • [ 1394124-54-9 ]
  • 10
  • [ 14752-66-0 ]
  • [ 1896-62-4 ]
  • [ 29869-86-1 ]
YieldReaction ConditionsOperation in experiment
74% With 1,4-diaza-bicyclo[2.2.2]octane; palladium(II) hydroxide; trifluoroacetic acid; In 1,4-dioxane; water; at 120℃; under 760.051 Torr; for 20h;Inert atmosphere; The reaction was conducted with Pd(OH)2 (1.4 mg, 0.01 mmol), DABCO (2.3 mg, 0.02 mmol),<strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (1f, 79.2 mg, 0.4 mmol), (E)-4-phenylbut-3-en-2-one (2a, 29.2mg, 0.2 mmol) and charged with argon (1 atm). TFA (0.1 mL, 6.7 equiv) and 1,4-dioxane (0.2 mL),H2O (0.2 mL) were added to the sealed reaction vessel by syringe. The resulting solution wasstirred at 120 C for 20 h. After cooling to room temperature, the volatiles were removed undervacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethylacetate = 30:1) to give 3p as pale yellow oil; yield 74%.
  • 11
  • [ 14204-24-1 ]
  • [ 14752-66-0 ]
  • [ 1142-97-8 ]
YieldReaction ConditionsOperation in experiment
72% With scandium tris(trifluoromethanesulfonate); In water; at 30℃; for 6h;Ionic liquid; General procedure: To a solution of 1 (0.3 mmol) and 2 (0.36 mmol) in [BMIM]PF6 (3 mL) and H2O (1 mL), Sc(OTf)3 was added at 30 C. The mixture solution was stirred at 30 C for respective time. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the mixture was washed with water and extracted with diethyl ether. The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired thiosulfonates 3.
  • 12
  • 1-[(4-bromophenyl)sulfanyl]pyrrolidine-2,5-dione [ No CAS ]
  • [ 14752-66-0 ]
  • S-(4-bromophenyl) 4-chlorobenzenesulfonothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With scandium tris(trifluoromethanesulfonate); In water; at 30℃; for 2h;Ionic liquid; General procedure: To a solution of 1 (0.3 mmol) and 2 (0.36 mmol) in [BMIM]PF6 (3 mL) and H2O (1 mL), Sc(OTf)3 was added at 30 C. The mixture solution was stirred at 30 C for respective time. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the mixture was washed with water and extracted with diethyl ether. The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired thiosulfonates 3.
  • 13
  • [ 14752-66-0 ]
  • [ 2050-68-2 ]
YieldReaction ConditionsOperation in experiment
87% With di-tert-butyl peroxide; palladium diacetate; In acetonitrile; at 60℃; for 12h; General procedure: A mixture of the sodium arylsulfinate (1 mmol), Pd(OAc)2 (1 mol%) and DTBP (0.5 mmol) was stirred at 60 C for 12 h in CH3CN (1 mL). Afterwards, the reaction solution was filtered through a filter paper and the organic phase was evaporated under reduced pressure at 40 C. The residue was purified on a SiO2 column (ethyl acetate/hexane = 1:20) to afford the desired product.
  • 14
  • [ 1407163-09-0 ]
  • [ 14752-66-0 ]
  • butyl 2-(4-chlorobenzyl)-3-(4-cyanophenyl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product.
  • 15
  • [ 37442-45-8 ]
  • [ 14752-66-0 ]
  • [ 859189-07-4 ]
YieldReaction ConditionsOperation in experiment
91% With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product.
  • 16
  • [ 603-76-9 ]
  • [ 14752-66-0 ]
  • [ 1555519-98-6 ]
YieldReaction ConditionsOperation in experiment
70% With tert.-butylhydroperoxide; iodine; In methanol; at 80℃; for 12h; General procedure: To a solution of N-methylindoles (1.0mmol), sodium aryl sulfonates (0.5mmol), catalyst I2 (0.75mmol) and tert-Butyl hydroperoxide (1.5mmol) in methanol (2mL) were added. The reaction mixture was stirred at 80C for 12h. Then the reaction mixture was cooled to room temperature, diluted with brine (15mL) and extracted with EtOAc (3×25mL). The organic layer dried over anhydrous MgSO4 and concentrated in vacuo. The residue was further purified by column chromatography on silica gel (Petroleum ether/EtOAc=5:1) to afford the compounds 6a, 7a-b, 8a-h, 9a-k, 10a-d with yield of 9%-95%.
  • 17
  • [ 100-42-5 ]
  • [ 14752-66-0 ]
  • [ 36603-45-9 ]
YieldReaction ConditionsOperation in experiment
90% With 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinatoiron(III) chloride; D-glucose; water monomer; oxygen; glucose oxidase; at 20℃; for 2h; General procedure: To a mixture of alkenes/alkynes (0.5 mmol), sodium benzenesulfinate(0.5 mmol), glucose (1.1 mmol) in water (2 ml), hemoproteins(heme concentration: 0.06 mol%), GOX (42 U/ml), was added. The reaction mixture was then stirred at room temperature in a round bottom flask for 2 h, with oxygen added at a rate of 1 mL/min. The reaction was monitored by TLC. When the reaction was complete, the crude mixture was extracted with ethyl acetate. Then the organic phase was dried over sodium sulfate and concentrated under reduced pressure. Finally, the desired product was obtained by flash column chromatography with petroleum ether/ethyl acetate (4/1) as an eluent. All the isolated products were well characterized by their 1H spectral analysis.
84% With copper chloride (II); In acetic acid; at 60℃; for 6h; General procedure: The reaction mixture of styrene 1a (0.5 mmol), sodium benzenesulfinate 2a (1.0 mmol), CuCl2(0.05 mmol) and 1 mL HOAc in 1 mL PEG400 in a 25 mL tube was stirred at 60 C for 6 h under air atmosphere and monitored periodically by TLC. Upon completion, the crude product was cooled to room temperature and then quenched by the addition of 5 mL water. The aqueous solution was extracted with ethyl acetate(3x5 mL) and the combined extracts were dried with anhydrous MgSO4. The solvent was removed under reduced pressure by an aspirator, and the crude product was purified by silica gel column chromatography with petroleum ether and ethyl acetate as eluent to afford the desired product 3a.
  • 18
  • [ 100-42-5 ]
  • [ 14752-66-0 ]
  • [ 1657-50-7 ]
YieldReaction ConditionsOperation in experiment
72% With ammonium hexafluorophosphate; 4,4′,5,5′-Tetrahydro-2,2′-bioxazole; acetic acid; palladium dichloride; In water; N,N-dimethyl-formamide; at 60℃; for 18h; General procedure: To a mixture of PdCl2 (5.3 mg, 0.03 mmol), 2,2’-bis(2-oxazoline) (4.6 mg, 0.033 mmol), and PhSO2Na(59.5 mg, 0.33 mmol) and NH4PF6 (14.7 mg, 0.09 mmol) in DMF (0.3 mL), H2O (0.2 mL) and AcOH(0.1 mL) were added styrene (31.2 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air.After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodiumchloride and dried over anhydrous magnesium sulfate
  • 19
  • [ 14752-66-0 ]
  • [ 536-74-3 ]
  • [ 36603-45-9 ]
YieldReaction ConditionsOperation in experiment
87% With iron(III) chloride; dipotassium peroxodisulfate; oxygen; In water; at 20℃; for 7h;Green chemistry; General procedure: A mixture of alkyne 1 (0.25 mmol), sodium sulfinate 2 (0.375 mmol), FeCl3 (20 mol %),K2S2O8 (20 mol %), and water (3 mL) was stirred at rt in an open flask for 6-9 h(Table 2). After completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 5 mL). The combined organic phases were dried over anhyd. Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of EtOAc-n-hexane (1:4) as eluent to afford an analytically pure sample of β-keto sulfones 3 (Table 2).
60% With heme b; D-glucose; water; oxygen; glucose oxidase; at 20℃; for 2h; General procedure: To a mixture of alkenes/alkynes (0.5 mmol), sodium benzenesulfinate(0.5 mmol), glucose (1.1 mmol) in water (2 ml), hemoproteins(heme concentration: 0.06 mol%), GOX (42 U/ml), was added. The reaction mixture was then stirred at room temperature in a round bottom flask for 2 h, with oxygen added at a rate of 1 mL/min. The reaction was monitored by TLC. When the reaction was complete, the crude mixture was extracted with ethyl acetate. Then the organic phase was dried over sodium sulfate and concentrated under reduced pressure. Finally, the desired product was obtained by flash column chromatography with petroleum ether/ethyl acetate (4/1) as an eluent. All the isolated products were well characterized by their 1H spectral analysis.
  • 20
  • [ 363-72-4 ]
  • [ 14752-66-0 ]
  • [ 29510-41-6 ]
YieldReaction ConditionsOperation in experiment
50% With bis(η3-allyl-μ-chloropalladium(II)); silver(l) oxide; XPhos; In water; N,N-dimethyl-formamide; at 110℃; for 20h;Schlenk technique; General procedure: [PdCl(allyl)]2 (36.6mg, 0.10mmol), Xphos (47.6mg, 0.10mmol), Ag2O (236.0mg, 1.0mmol) and sodium arylsulfinate (0.50mmol) were added to a Schlenk tube that was equipped with a stirring bar. Wet DMF (5.0mL, containing 1vol% of H2O) was added into this tube, polyfluoroarene (1.0mmol) were added in turn to the Schlenk tube through the rubber septum via syringe. The tube was capped with a septum and taken out. The reaction mixture was stirred at 110C for 20h. After cooling down, the reaction mixture was diluted with 10mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (10mL). The filtrate was washed with water (3× 10mL). The organic phase was dried over MgSO4, filtered, concentrated in vacuo. The residue was then purified by flash chromatography on silica gel to provide the corresponding product.
  • 21
  • [ 14752-66-0 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 80-00-2 ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; sodium acetate; In 1,2-dichloro-ethane; at 25℃; for 3h; General procedure: A mixture of potassium arylfluoborate (1 mmol), sodium aryl sulfinate (1 mmol), CuI (0.1 mmol), sodium acetate (1.2 mmol) and DCE (2 mL) was stirred at 25 C under air for 3 h. After filtration, the organic phases were evaporated under reduced pressure, and the residue was subjected to flash column chromatography [silica gel, ethyl acetate/petroleum ether (60-90 C) = 1/8] to obtain the desired product.
  • 22
  • [ 591-50-4 ]
  • [ 14752-66-0 ]
  • [ 80-00-2 ]
YieldReaction ConditionsOperation in experiment
80% With C93H189NO41; copper(I) bromide; In water; at 120℃; for 20h; Put iodobenzene (1mmol, 0.204g) into a 30mL test tube with a stopper,Sodium p-chlorobenzenesulfinate (1.2mmol, 0.238g),Surfactant M2070 (0.3mmol, 0.6g),Cuprous bromide (0.13mmol, 0.0186g),Add 10mL of water,The reaction was stirred at 120C for 20 hours.After cooling, 1g of sodium chloride was added, heated to a cloud point of 80C for extraction, heated to a cloud point of 80C for extraction, and separated into a lower water-rich phase and an upper surface-rich phase. Take out the rich surface layer, heat the rich surface phase (containing a large amount of surfactants and reaction substances), centrifuge at high speed to precipitate the surfactant, take the supernatant, and separate the aryl sulfone compound. High performance liquid chromatography proves that the extraction efficiency is 100%. The yield of aryl sulfone product was 80%.
  • 23
  • [ 14752-66-0 ]
  • [ 1885-29-6 ]
  • [ 2894-51-1 ]
YieldReaction ConditionsOperation in experiment
83% With p-nitrobenzenesulfonic acid; palladium diacetate; In tetrahydrofuran; water; at 80℃; for 48h;Inert atmosphere; Schlenk technique; General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol %), bpy (20 mol %), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.
  • 24
  • [ 14752-66-0 ]
  • [ 80-07-9 ]
YieldReaction ConditionsOperation in experiment
94% With copper diacetate; In acetonitrile; at 60℃; for 3h; General procedure: A mixture of the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS.
  • 25
  • [ 14752-66-0 ]
  • [ 2156-56-1 ]
  • [ 5943-04-4 ]
YieldReaction ConditionsOperation in experiment
74% In water; at 90.0℃; for 7.0h; To the solution of salt 3 (3.97 g, 20 mmol) in water(20mL) <strong>[2156-56-1]sodium dichloroacetate</strong> (3.77 g, 2.5 mmol) was added. The mixture was stirred andheated at 90Cfor 7 hours, kipping pH ~7, by dropping 30% solution of natrium hydroxide. Aftercooling to the room temperature the precipitate was filtered off, washed bywarm water and dried. The product 7 waspurified by recrystallization from ethanol. Chloromethyl-4-chlorophenyl sulfone8 was obtained in 74% yield. M.p. = 120-121C. IR (cm-1):2970 (CHaliph.), 1600 (CHar), 1320, 1140 (SO2).1H-NMR, 400MHz, (CDCl3) delta: 4.53 (s, 2H);7.58-7.60 (m, 2H); 7.90- 7.92 (m. 2H). 13C NMR (100 MHz, CDCl3) delta: 65.99; 124.03;127.47; 132.49; 146.27. Elemental analysis: for C7H6Cl2O2S(225.09) Calcd.: 37.35 % C, 2.69 %H. Found: 37.33 % C, 2.72 % H.
  • 26
  • [ 55577-25-8 ]
  • [ 14752-66-0 ]
  • [ 100-52-7 ]
  • C28H22ClNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In ethyl acetate; at 20℃; for 2h; General procedure: 2-Phenylindole (0.58 g, 3 mmol), TsOH·H2O (0.29 g, 1.5 mmol), 4-chlorobenzenesulfinic acid sodium salt(0.59 g, 3 mmol), and benzaldehyde (0.31 mL, 3 mmol) were placed in a round bottom flask and suspended inethyl acetate. The mixture was stirred at room temperature for 2 h, and was then diluted with water. Theresulting white precipitate was collected and washed with ether to afford analytically pure 2d (0.54 g, 1.2mmol, 40%).
 

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