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[ CAS No. 824-80-6 ]

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Chemical Structure| 824-80-6
Chemical Structure| 824-80-6
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Product Details of [ 824-80-6 ]

CAS No. :824-80-6 MDL No. :MFCD03093775
Formula : C6H4FNaO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :182.15 g/mol Pubchem ID :23666220
Synonyms :

Safety of [ 824-80-6 ]

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 [ 824-80-6 ]

  • Downstream synthetic route of [ 824-80-6 ]

[ 824-80-6 ] Synthesis Path-Downstream   1~25

  • 1
  • (+)-3-chloro-2-hydroxy-2-methyl propionic acid [ No CAS ]
  • [ 824-80-6 ]
  • (-)-3-(4-fluoro-benzenesulfonyl)-2-hydroxy-2-methyl propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Example 3 (-)-3-(4-Fluoro-benzenesulfonyl)-2-hydroxy-2-methyl propionic acid 1.38 g (10 mmol) of (+)-2-hydroxy-2-methyl-3-chloro propionic acid ((+)XIV, Example 2), 2.91 g (16 mmol) of sodium 4-fluorophenyl-sulfinate, 5 g of sodium carbonate, 5 cm3 of water and 1.0 g tetrabutyl ammonium chloride was placed into a round-bottomed flask. After refluxing the reaction mixture for 24 hours it was diluted with 30 cm3 of water, cooled to ambient temperature and the pH of the reaction mixture was adjusted to pH=3 by careful addition of concentrated hydrochloric acid. The reaction mixture was extracted with 6 x 50 cm3 of ethyl acetate, the combined organic phases were dried and evaporated, finally the evaporation residue was purified by refluxing with dichloromethane. Yield: 1.2 g (46%). Specific rotation: [alpha]=-3.3 (c=1, methanol, lambda=589 nm, I=1 dm). Melting point: 125-126C.
  • 2
  • [ 929093-95-8 ]
  • [ 824-80-6 ]
  • [ 929093-96-9 ]
YieldReaction ConditionsOperation in experiment
32% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 120℃; Step 3: Preparation of [3-butoxy-5-(4-fluoro-benzenesulfonyl)-phenyl]-acetic acid methyl ester (11); To a solution of (3-butoxy-5-trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester (10, 198 mg, 0.000535 mol) and sodium 4-fluoro-benzenesulfinate (120 mg, 0.00064 mol) dissolved in toluene (4 mL, 0.04 mol) in a sealable reaction vessel, tris(dibenzylideneacetone)dipalladium(0) (49 mg, 0.000053 mol), cesium carbonate (260 mg, 0.00080 mol), and xanthphos (60 mg, 0.0001 mol) were added under an argon atmosphere. The vessel was sealed and the mixture was heated overnight at 120 C. After cooling, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated and put on silica. Flash chromatography (hexane/ethyl acetate 9:1) yielded the desired compound (11, 65 mg, 32%).
  • 3
  • [ 40273-47-0 ]
  • [ 824-80-6 ]
  • [ 1161864-78-3 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 100℃; for 72h; A solution of <strong>[40273-47-0]3-fluoroisonicotinaldehyde</strong> (0.25 mL) in dimethyl sulfoxide (2.0 mL) was treated with a solution of 4-fluorobenzene sulfinic acid sodium salt (0.5 g) in dimethyl sulfoxide (3.0 mL), and the resulting mixture was stirred at 1000C for 3 days. The mixture was cooled to room temperature, partitioned between water and ethyl acetate (20 mL), and the aqueous phase extracted with ethyl acetate. The combined organic solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1 :0 to 4:1 by volume) to afford the title compound as a white solid (0.38 g). <n="22"/>1H NMR (CDCI3): delta 7.24-7.29 (m, 2H)1 7.76 (dd, J = 0.7, 4.9 Hz, 1 H), 7.95-8.01 (m, 2H), 9.02 (d, J = 4.9 Hz, 1 H), 9.30 (s, 1 H), 10.88 (d, J = 0.7 Hz, 1 H).
  • 4
  • [ 824-80-6 ]
  • [ 131184-73-1 ]
  • [ 1194551-63-7 ]
  • 5
  • [ 273-53-0 ]
  • [ 824-80-6 ]
  • [ 397-54-6 ]
YieldReaction ConditionsOperation in experiment
76% 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.
  • 6
  • [ 14135-38-7 ]
  • [ 824-80-6 ]
  • [ 1394124-51-6 ]
  • 7
  • [ 824-80-6 ]
  • [ 1896-62-4 ]
  • 4-(4-fluorophenyl)-4-phenylbutan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% 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>[824-80-6]sodium 4-fluorobenzenesulfinate</strong> (1e, 72.8 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 3o as pale yellow oil; yield 80%.
  • 8
  • [ 14204-24-1 ]
  • [ 824-80-6 ]
  • p-fluorophenylsulfonothioic phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% 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.
  • 9
  • 1-[(4-bromophenyl)sulfanyl]pyrrolidine-2,5-dione [ No CAS ]
  • [ 824-80-6 ]
  • [ 1415245-44-1 ]
YieldReaction ConditionsOperation in experiment
73% 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.
  • 10
  • [ 824-80-6 ]
  • [ 398-23-2 ]
YieldReaction ConditionsOperation in experiment
89% 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.
  • 11
  • [ 824-80-6 ]
  • [ 536-74-3 ]
  • [ 432-99-5 ]
YieldReaction ConditionsOperation in experiment
84% With iron(III) chloride; dipotassium peroxodisulfate; oxygen; In water; at 20℃; for 8h;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 beta-keto sulfones 3 (Table 2).
  • 12
  • [ 363-72-4 ]
  • [ 824-80-6 ]
  • [ 29778-93-6 ]
YieldReaction ConditionsOperation in experiment
38% With bis(eta3-allyl-mu-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.
  • 13
  • [ 824-80-6 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 312-31-2 ]
YieldReaction ConditionsOperation in experiment
89% 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.
  • 14
  • [ 824-80-6 ]
  • [ 1885-29-6 ]
  • [ 3800-06-4 ]
YieldReaction ConditionsOperation in experiment
81% 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.
  • 15
  • [ 824-80-6 ]
  • [ 383-29-9 ]
YieldReaction ConditionsOperation in experiment
88% 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.
  • 16
  • [ 824-80-6 ]
  • [ 106-96-7 ]
  • [ 1628709-34-1 ]
YieldReaction ConditionsOperation in experiment
65% General procedure: n-Bu4NF (1.0 M in THF, 0.2 mL, 0.2 mmol) was added to a solution of propargyl bromide (2a) (80% in toluene, 150 mg, 1.0 mmol)or 1-bromopent-2-yne (2b) (150 mg, 1.0 mmol) in 1,4-dioxane (5 mL) at rt. Then, RSO2Na (3a-k) (3.0 mmol) in hot water (1 mL) was slowly added to the reaction mixture. The reaction mixture was stirred at rt for 10 min. Next, Pd/C (10% in carbon, 11 mg, 0.1 mmol) was added to the stirred solution at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled, filtered, washed, and concentrated under reduced pressure. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc = 6/1~2/1) afforded skeleton 1.
  • 17
  • [ 34179-62-9 ]
  • [ 824-80-6 ]
  • [ 1423121-04-3 ]
YieldReaction ConditionsOperation in experiment
78% With copper diacetate; palladium diacetate; In 1,4-dioxane; diethylene glycol dimethyl ether; at 120℃; for 24h; General procedure: A reaction vessel was charged with thiazolo[3,2-b]-1,2,4-triazoles 1 (0.5 mmol), sodium arylsulfinates 2 (1 mmol),Pd(OAc)2 (5 mol%), Cu(OAc)2 (2 equiv), and dioxane-diglyme (1:2; 1 mL). The mixture was stirred at 120 C andmonitored by TLC. After the completion of the reaction, themixture was poured into H2O (10 mL), and extracted withEtOAc (3 × 10 mL). The combined extract was dried withanhyd MgSO4. The solvent was removed and the crudeproduct was separated by column chromatography (elutedwith petroleum ether-EtOAc) to give the desired products 3and 4.
  • 18
  • [ 824-80-6 ]
  • [ 32189-03-0 ]
  • [ 1423120-71-1 ]
YieldReaction ConditionsOperation in experiment
80% With copper diacetate; palladium diacetate; In 1,4-dioxane; diethylene glycol dimethyl ether; at 120℃; for 24h; General procedure: A reaction vessel was charged with thiazolo[3,2-b]-1,2,4-triazoles 1 (0.5 mmol), sodium arylsulfinates 2 (1 mmol),Pd(OAc)2 (5 mol%), Cu(OAc)2 (2 equiv), and dioxane-diglyme (1:2; 1 mL). The mixture was stirred at 120 C andmonitored by TLC. After the completion of the reaction, themixture was poured into H2O (10 mL), and extracted withEtOAc (3 × 10 mL). The combined extract was dried withanhyd MgSO4. The solvent was removed and the crudeproduct was separated by column chromatography (elutedwith petroleum ether-EtOAc) to give the desired products 3and 4.
  • 19
  • [ 640-60-8 ]
  • [ 824-80-6 ]
  • [ 312-31-2 ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(actonitrile)copper(I) hexafluorophosphate; In dimethyl sulfoxide; at 120℃; General procedure: A mixture of the sodium arylsulfinate (1 mmol), aryl tosylate (1 mmol), [Cu(CH3CN)4]PF6 (0.1 mmol) and DMSO (2 mL) was stirred at 120 C under air for 6 h. After wards, water (2 mL) was added to the reaction solution which was then filtered and the solution extracted by Et2O (3 × 2 mL). The organic phases were combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (eluent; ethyl acetate/hexane 1 : 15).
  • 20
  • [ 91-63-4 ]
  • [ 824-80-6 ]
  • 2-(((4-fluorophenyl)sulfonyl)methyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tert-Butyl peroxybenzoate; tetra-(n-butyl)ammonium iodide; In water; at 100℃; for 10h;Sealed tube; Green chemistry; General procedure: A sealable reaction tube equipped with a magnetic stirrer bar was charged with azaarenes (1.0 mmol), sodium benzenesulfinate (2 equiv), TBAI (0.2 equiv), tert-butyl peroxybenzoate (TBPB, 1 equiv), and water (1 ml). The reaction was carried out at 100 C. After completion, the result was diluted with diethyl ether, washed with water and brine, and dried with Mg2SO4. After solvent removal under reduced pressure, the residue was purified by column chromatography on silica gel to afford the corresponding product.
  • 21
  • [ 824-80-6 ]
  • [ 402-46-0 ]
  • 22
  • [ 127425-73-4 ]
  • [ 824-80-6 ]
  • 1-bromo-2-fluoro-4-(((4-fluorophenyl)sulfonyl)methyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.95 g In N,N-dimethyl-formamide; at 20 - 70℃; for 3h; Step B: 1-bromo-2-fluoro-4-(((4-fluorophenyl)sulfonyl)methyl)benzene Sodium 4-fluorobenzenesulfinate (15.42 g, 85 mmol) was added in several portions to a stirred solution of impure <strong>[127425-73-4]1-bromo-4-(bromomethyl)-2-fluorobenzene</strong> (28.21 g, 70.5 mmol, ?67% pure) in DMF (80 mL). The mixture warmed up slightly during the addition. The mixture was stirred at ambient temperature for 1 h and at 70 C. for 2 h. After cooling to rt, the mixture was diluted with EtOAc (500 mL), washed with water (2*250 mL), brine (50 mL), dried (MgSO4) and concentrated. The white residue was treated with CH2Cl2 (20 mL) and hexanes (200 mL), sonicated to break up solid chunks, stirred for 30 min, and filtered. The filter cake was washed with hexanes (200 mL) and dried under vacuum to give the desired product as white solid (22.95 g). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.73-7.64 (m, 2H), 7.47 (dd, J=8.1, 7.0 Hz, 1H), 7.22-7.14 (m, 2H), 6.93 (dd, J=8.9, 2.0 Hz, 1H), 6.76 (dd, J=8.2, 1.6 Hz, 1H), 4.25 (s, 2H).
  • 23
  • [ 824-80-6 ]
  • [ 68-12-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
42% General procedure: An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with formamide 1 (2.0 mmol), KO-t-Bu (2.0 mmol) and CH3CN (2.0 mL). The mixture was stirred at 50 C for 30 min and then a CH3CN (2.0 mL) solution containing sodium sulfinates 2 (0.5 mmol) and NIS (1.0 mmol) was slowly added dropwise. The resulting solution stirred at 50 C for 12 h under air. The mixture was then cooled to room temperature, diluted with 30 mL of H2O, and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the products.
  • 24
  • [ 20035-08-9 ]
  • [ 824-80-6 ]
  • S-(4-fluorophenyl) ethanesulfonothioate [ No CAS ]
  • 25
  • [ 3476-89-9 ]
  • [ 824-80-6 ]
  • C14H9FN2O2S [ No CAS ]
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