873-55-2

Basic information

• Product Name: Sodium benzenesulfinate
• Synonyms: 4-CHLOROBENZENESULPHINIC ACID SODIUM SALT;4-CHLOROBENZENESULFINIC ACID SODIUM SALT HYDRATE;SODIUM 4-CHLOROBENZENE SULFINIC ACID;P-CHLOROBENZENESULFINIC ACID SODIUM SALT;Sodium benzene sulfonate,Sodium benzosulfonate ;BENZENESULFINIC ACID NA SALT;Natriumbenzolsulfinat;Benzenesulfinic acid sodium salt
• CAS NO: 873-55-2
• Molecular Formula: C₆H₅O₂S*Na
• Molecular Weight: 164.16
• EINECS: 212-842-8
• Product Categories: Industrial/Fine Chemicals;Pharmaceutical Intermediates
• Mol File: 873-55-2.mol
• Article Data: 59

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 339.4 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: White/Crystals or Crystalline Powder
• Density: 0.8 g/cm3 (20oC)
• Vapor Pressure: 3.58E-05mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Solubility: Water
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• BRN: 3598405
• CAS DataBase Reference: Sodium benzenesulfinate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium benzenesulfinate(873-55-2)
• EPA Substance Registry System: Sodium benzenesulfinate(873-55-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36-24/25
• WGK Germany: 1
• RTECS: DA9135000
• TSCA: T
• Hazardous Substances Data: 873-55-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 873-55-2 differently. You can refer to the following data:
1. Benzenesulfinic Acid Sodium Salt is used reduce the adverse chemical interaction involved in the coupling of self/dual-cured composites to hydrated dentin.
2. It is used as a polymer adhesive enhancers, plasticizers for plasticized and modified of polyamide, epoxy resin, phenolic resin. It is designed for manufacturing of photography, pharmaceutical, electroplating industry, can be used as photo-reducing agent.
3. Benzenesulfinic acid sodium salt has been used in synthesis of sulfones by reaction of organic halides and sodium benzenesulfinate using higher alcohols or diols as solvents.It was also used in the synthesis of aryl sulfones via copper-catalyzed cross-coupling with boronic acids and vinyl sulfones via reaction with vicinal dibromides.

General Description

Benzenesulfinic acid sodium salt when treated with alkynylselenonium salts yields (Z)-β-alkoxyvinylsulfones. It undergoes rhodium-catalyzed desulfinative coupling with aldehydes to yield ketones.

Purification Methods

Dissolve it in the minimum volume of O2 free H2O (prepared by bubbling N2 through for 2 hours) and adding O2 free EtOH (prepared as for H2O), set aside at 4o overnight under N2, filter, wash with EtOH, then Et2O and dry in vacuo. The Na salt is relatively stable to air oxidation, but is best kept under N2 in the dark. Also recrystallise it from EtOH and dry it at 120o for 4hours in a vacuum. [Kornblum & Wade J Org Chem 52 5301 1987, Beilstein 11 II 2, 11 IV 3.]

InChI:InChI:1S/C6H6O2S.Na/c7-9(8)6-4-2-1-3-5-6;/h1-5H,(H,7,8);/q;+1/p-1

Synthetic route

2-nitrophenylphenyl sulfone + sodium thiophenolate (930-69-8) + thiophenol (108-98-5) → 2-nitrophenylphenyl sulfide + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium hydroxide In methanol; water; toluene	A 96.7% B 97.1%

benzenesulfonyl chloride (98-09-9) → sodium benzenesulfonate (873-55-2)

Conditions	Yield
With hydrazine hydrate; sodium carbonate In water at 60℃; for 2h; Reagent/catalyst;	96.5%
With sodium hydrogencarbonate; sodium sulfite In water at 70 - 80℃; for 2h;	88%
With sodium iodide In acetone for 3h; Ambient temperature; Yield given;

diphenyliodonium tetrafluoroborate → sodium benzenesulfonate (873-55-2)

Conditions	Yield
With iron(III) chloride; rongalite In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.333333h; Solvent; Reagent/catalyst;	96%

2-nitrophenylphenyl sulfone + sodium thiophenolate (930-69-8) → 2-nitrophenylphenyl sulfide + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In methanol; water; toluene	A n/a B 95.8%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) + sodium ethanolate (141-52-6) → 2,4-dinitro-benzenesulfenic acid ethyl ester (2388-58-1) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In ethanol at -2℃; for 4h;	A 92.2% B 76%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) → 2,4-dinitro-benzenesulfenic acid ethyl ester (2388-58-1) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium ethanolate In ethanol at -2℃; for 4h;	A 92.2% B 76%

2-(phenylsulfonyl)pyridine (24244-60-8) + sodium ethanolate (141-52-6) → 2-ethoxypyridine (14529-53-4) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In ethanol for 19h; Heating;	A n/a B 92%
In ethanol for 0.2h; Heating;	A 87 % Spectr. B 63 % Spectr.

ethanol (64-17-5) + 2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) → 2,4-dinitro-benzenesulfenic acid ethyl ester (2388-58-1) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium for 4h;	A 92% B 76%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) + acetylacetone (123-54-6) → 3-<2,4-Dinitro-phenylmercapto>-pentandion-(2,4) (25108-45-6) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium ethanolate In ethanol at 50℃; for 2h;	A 91.2% B 89.7%

C21H21N3O2S (90959-41-4) → 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (14929-23-8) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A 90% B n/a

phenylmagnesium chloride (100-59-4) → sodium benzenesulfonate (873-55-2)

Conditions	Yield
Stage #1: phenylmagnesium chloride With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Stage #2: With sodium carbonate In tetrahydrofuran; diethyl ether; water	90%

2-benzenesulfonyl-pyridine N-oxide (39574-20-4) + sodium ethanolate (141-52-6) → 2-ethoxylpyridine N-oxide (3445-09-8) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In ethanol for 0.25h; Heating;	A n/a B 89%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) + ethyl acetoacetate (141-97-9) → 2-oxo-1-ethoxycarbonylpropyl 2,4-dinitrophenyl sulfide (55158-57-1) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 1h;	A 85.4% B 74.6%

2-Benzenesulfinyl-pyridine 1-oxide (125556-92-5) → 2-ethoxylpyridine N-oxide (3445-09-8) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium ethanolate In ethanol for 0.5h;	A 85% B 74%
With sodium ethanolate In ethanol for 0.5h; Mechanism; effect of absence of air;	A 85% B 74%

bromobenzene (108-86-1) → sodium benzenesulfonate (873-55-2)

Conditions	Yield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; Stage #3: With sodium carbonate In tetrahydrofuran; diethyl ether; water Reagent/catalyst; Temperature;	85%

C30H29ClN2O7S2 (95361-36-7) → sodium benzenesulfonate (873-55-2) + p-methoxybenzyl 7β-(2-phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate (104146-10-3)

Conditions	Yield
With sodium methylate In tetrahydrofuran; methanol at -2 - 2℃; for 5.25h; Product distribution / selectivity;	A 67.9% B 84.6%

C20H18ClN3O2S (90959-34-5) → sodium benzenesulfonate (873-55-2) + 4-(4-Chloro-phenyl)-3-phenyl-4H-[1,2,4]triazole

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A n/a B 80%

α-anthraquinonyl benzenethiosulfonate (94055-55-7) + sodium ethanolate (141-52-6) → 9,10-dioxo-9,10-dihydro-anthracene-1-sulfenic acid ethyl ester (39674-32-3) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In ethanol at 20℃; for 10h;	A 77.5% B 79.3%

C20H19N3O2S (90959-31-2) → 3,4-diphenyl-1,2,4-triazole (14331-64-7) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A 78% B n/a

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) → bis(2,4-dinitrophenyl) disulphide (2217-55-2) + sodium benzenesulfonate (873-55-2) + 2,4-dinitrophenylthiocyanoacetic ester (91611-42-6)

Conditions	Yield
With sodium ethanolate; ethyl 2-cyanoacetate In ethanol at 50℃; for 3h;	A 52.2% B 70.2% C 43.7%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) + ethyl 2-cyanoacetate (105-56-6) → bis(2,4-dinitrophenyl) disulphide (2217-55-2) + sodium benzenesulfonate (873-55-2) + 2,4-dinitrophenylthiocyanoacetic ester (91611-42-6)

Conditions	Yield
With sodium ethanolate In ethanol at 50℃; for 3h;	A 52.2% B 70.2% C 43.7%
With sodium ethanolate In ethanol at 50℃; for 3h;	A 52.2% B 70.2% C 43.7%

2,4-dinitrophenyl benzenethiosulfonate (24040-12-8) + sodium methylate (124-41-4) → dinitrobenzenesulfenic acid methyl ester (10344-04-4) + sodium benzenesulfonate (873-55-2)

Conditions	Yield
In methanol at 20℃; for 1h;	A 58% B 70%

C21H21N3O3S (90959-33-4) → sodium benzenesulfonate (873-55-2) + 4-(4-methoxyphenyl)-3-phenyl-4H-1,2,4-triazole (70208-16-1)

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A n/a B 63%

C21H20ClN3O2S (90959-42-5) → sodium benzenesulfonate (873-55-2) + 4-(4-Chloro-phenyl)-3-methyl-5-phenyl-4H-[1,2,4]triazole

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A n/a B 63%

α-anthraquinonyl benzenethiosulfonate (94055-55-7) → bis(1-anthraquinonyl) disulfide (13354-33-1) + sodium benzenesulfonate (873-55-2) + Cyano-(9,10-dioxo-9,10-dihydro-anthracen-1-ylsulfanyl)-acetic acid ethyl ester (94055-23-9)

Conditions	Yield
With sodium ethanolate; ethyl 2-cyanoacetate In ethanol at 50℃; for 4h;	A 37.6% B 59.9% C 34.2%

α-anthraquinonyl benzenethiosulfonate (94055-55-7) + ethyl 2-cyanoacetate (105-56-6) → bis(1-anthraquinonyl) disulfide (13354-33-1) + sodium benzenesulfonate (873-55-2) + Cyano-(9,10-dioxo-9,10-dihydro-anthracen-1-ylsulfanyl)-acetic acid ethyl ester (94055-23-9)

Conditions	Yield
With sodium ethanolate In ethanol at 50℃; for 4h;	A 37.6% B 59.9% C 34.2%
With sodium ethanolate In ethanol at 50℃;

C21H21N3O2S (90959-32-3) → sodium benzenesulfonate (873-55-2) + 4-(4-methylphenyl)-3-phenyl-4H-1,2,4-triazole (14331-67-0)

Conditions	Yield
With sodium hydride In 1,4-dioxane for 20h; Heating; under nitrogen; Yields of byproduct given;	A n/a B 57%

Allyl acetate (591-87-7) + sodium benzenesulfonate (873-55-2) → (allylsulfonyl)benzene (16212-05-8)

Conditions	Yield
With triphenylphosphine; Pd-Gr In tetrahydrofuran; water for 0.5h; Product distribution; Mechanism; Heating; other allylic esters; other palladium catalysts; other solvents; also diethyl malonate and 1-(1-cyclohexen-1-yl)pyrrolidine as nucleophiles;	100%
With triphenylphosphine; Pd-Gr In tetrahydrofuran; water for 0.5h; Heating;	100%
With trisodium tris(3-sulfophenyl)phosphine; 1-ethyl-3-methylimidazolium tetrafluoroborate; palladium diacetate In water for 0.0333333h; Tsuji-Trost reaction; microwave irradiation;	99%

N,N-diethylacrylamide (2675-94-7) + sodium benzenesulfonate (873-55-2) → 3-Benzenesulfonyl-N,N-diethyl-propionamide (93101-87-2)

Conditions	Yield
With acetic acid In water for 8h; Heating;	100%

ethyl (E)-2-(bromomethyl)but-2-enoate (62097-05-6) + sodium benzenesulfonate (873-55-2) → (Z)-2-Benzenesulfonylmethyl-but-2-enoic acid ethyl ester (136540-17-5)

Conditions	Yield
With PEO 400 In tetrahydrofuran for 1h; Heating;	100%

p-(1-methyl-1-nitropropyl)nitrobenzene (110637-93-9, 58324-83-7) + sodium benzenesulfonate (873-55-2) → 2-(p-nitrophenyl)-2-butyl phenyl sulfone (110637-98-4)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide for 2h;	100%

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5, 78963-47-0, 78963-48-1, 78963-60-7, 80951-41-3, 81275-02-7, 85647-75-2, 85954-95-6, 92217-74-8, 104527-11-9, 76855-69-1) + sodium benzenesulfonate (873-55-2) → (3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one (383186-38-7)

Conditions	Yield
In water for 0.333333h; Inert atmosphere; Reflux;	100%
In tetrahydrofuran; water for 0.75h; Heating;	90%
	84%
In water

sodium benzenesulfonate (873-55-2) → sodium phenylthiosulfonate (1887-29-2)

Conditions	Yield
With sulfur; N-butylamine at 20℃; for 1h; Other amines. In a titanium autoclave.;	100%
With 5,6,7,8,9-pentathiabenzocycloheptene In methanol; benzene for 5h; Ambient temperature;	99%
With pyridine; sulfur at 20℃; for 24h; Large scale;	92%

sodium benzenesulfonate (873-55-2) + 2-(bromomethyl)-5-nitrofuran (20782-91-6) → 5-nitro-2-furfuryl phenyl sulphone (40941-17-1)

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 4h;	100%
In acetone

sodium benzenesulfonate (873-55-2) + α-bromoacetophenone (70-11-1) → 2-(phenylsulfonyl)acetophenone (3406-03-9)

Conditions	Yield
In 1,4-dioxane; water Reflux;	100%
With aluminum oxide for 2h; Irradiation;	98%
With PEG-400 at 20℃; for 0.166667h;	96%

tert-butyl carbamate (4248-19-5) + sodium benzenesulfonate (873-55-2) + benzaldehyde (100-52-7) → tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7)

Conditions	Yield
With formic acid In methanol; water at 20℃; for 72h;	100%
In methanol; formic acid; water at 20℃; for 72h;	99%
In methanol; formic acid; water at 20℃; for 72h;	98%

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5, 78963-47-0, 78963-48-1, 78963-60-7, 80951-41-3, 81275-02-7, 85647-75-2, 85954-95-6, 92217-74-8, 104527-11-9, 76855-69-1) + sodium benzenesulfonate (873-55-2) → (3S,4R)-4-benzenesulfonyl-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 4h;	100%

sodium benzenesulfonate (873-55-2) + (Z)-3-Chloromethyl-4-naphthalen-1-yl-but-3-en-2-one (263141-35-1) → (Z)-3-Benzenesulfonylmethyl-4-naphthalen-1-yl-but-3-en-2-one

Conditions	Yield
With 1-n-butyl-methylimidazolium tetrafluoroborate at 45 - 50℃; for 2h;	100%

sodium benzenesulfonate (873-55-2) + (Z)-3-Chloromethyl-4-(4-fluoro-phenyl)-but-3-en-2-one → (Z)-3-Benzenesulfonylmethyl-4-(4-fluoro-phenyl)-but-3-en-2-one

Conditions	Yield
With 1-n-butyl-methylimidazolium tetrafluoroborate at 45 - 50℃; for 2h;	100%

sodium benzenesulfonate (873-55-2) + 2,4-Dichlorobenzyl chloride (94-99-5) → {[(2,4-dichlorophenyl)methyl]sulfonyl}benzene (90691-46-6)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃; for 4h;	100%

(4S)-11-{2-[(3-bromopropyl)-dimethylsilanyl]-ethyI}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (1142936-66-0) + sodium benzenesulfonate (873-55-2) → (4S)-11-{2-[(3-benzenesulfonylpropyl)-dimethylsilanyl]-ethyl}-4-ethyI-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (1142936-70-6)

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 5h;	100%
In N,N-dimethyl-formamide at 70℃; for 5h;	100%

O-benzyl carbamate (621-84-1) + sodium benzenesulfonate (873-55-2) + 4-cyanobenzaldehyde (105-07-7) → benzyl (4-cyanophenyl)(phenylsulfonyl)methylcarbamate (1220349-77-8)

Conditions	Yield
With formic acid In tetrahydrofuran; water at 22℃; Inert atmosphere;	100%

3-(iodomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-[1,2]oxazine 2-oxide (1215082-84-0) + sodium benzenesulfonate (873-55-2) → 6,6-dimethyl-4-phenyl-3-[(phenylsulfonyl)methyl]-5,6-dihydro-4H-[1,2]oxazine 2-oxide (1313227-80-3)

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%

1-phenyl 2-nitrosoterephthalate (1391926-97-8) + sodium benzenesulfonate (873-55-2) → N-benzenesulfonyl 5-carboxylic benzo[c]isoxazol-3(1H)-one (123534-37-2)

Conditions	Yield
at 20℃; for 0.166667h; pH=7; Inert atmosphere; aq. phosphate buffer; chemoselective reaction;	100%

2,6-bis-(bromomethyl)pyridine (7703-74-4) + sodium benzenesulfonate (873-55-2) → 2,6-bis[(phenylsulfonyl)methyl]pyridine

Conditions	Yield
With tetra-n-propylammonium bromide In acetonitrile for 24h;	100%
With tetra-n-propylammonium bromide In acetonitrile for 24h;	87%

C23H24O3 + sodium benzenesulfonate (873-55-2) → 1-((S)-2-methoxy-1-phenylethoxy)-2-[(phenylsulfonyl)(o-tolyl)methyl]benzene

Conditions	Yield
With chloro-trimethyl-silane; tin(II) bromide In nitromethane at -15℃; for 1h; Inert atmosphere; diastereoselective reaction;	100%

C23H24O4 + sodium benzenesulfonate (873-55-2) → 1-((S)-2-methoxy-1-phenylethoxy)-2-[(2-methoxyphenyl)(phenylsulfonyl)methyl]benzene

Conditions	Yield
With chloro-trimethyl-silane; tin(II) bromide In nitromethane at -15℃; for 0.5h; Inert atmosphere; diastereoselective reaction;	100%

C22H21ClO3 + sodium benzenesulfonate (873-55-2) → 1-[(4-chlorophenyl)(phenylsulfonyl)methyl]-2-((S)-2-methoxy-1-phenylethoxy)benzene

Conditions	Yield
With chloro-trimethyl-silane; tin(II) bromide In nitromethane at -15℃; for 24h; Inert atmosphere; diastereoselective reaction;	100%

C26H24O3 + sodium benzenesulfonate (873-55-2) → 1-[{2-((S)-2-methoxy-1-phenylethoxy)phenyl}(phenylsulfonyl)methyl]naphthalene

Conditions	Yield
With chloro-trimethyl-silane; tin(II) bromide In nitromethane; dichloromethane at -40℃; for 24h; Temperature; Solvent; Inert atmosphere; diastereoselective reaction;	100%

sodium benzenesulfonate (873-55-2) → benzenesulfonyl iodide (1950-77-2)

Conditions	Yield
With ammonium iodide; acetic acid at 60℃;	99%
With (NaI)2ICl(C3H6O)6 In water	79%
With ethanol; water; iodine
With iodine In ethanol; water at 5℃;

sodium benzenesulfonate (873-55-2) + benzyl chloride (100-44-7) → Benzyl phenyl sulfone (3112-88-7)

Conditions	Yield
With aluminum oxide for 2h; Irradiation;	99%
With 1-butyl-3-methylimidazolium Tetrafluoroborate In water at 60℃; for 2h;	96%
In N,N-dimethyl-formamide at 80℃; for 12h;	96%

sodium benzenesulfonate (873-55-2) + methyl vinyl ketone (78-94-4) → 4-(phenylsulfonyl)butan-2-one (24731-39-3)

Conditions	Yield
With potassium dihydrogenphosphate In water at 20℃; for 48h;	99%
	91%
With acetic acid for 14h; Ambient temperature;	81%
With potassium dihydrogenphosphate In water

SEC-BUTYLAMINE (33966-50-6) + sodium benzenesulfonate (873-55-2) → N-sec-Butylbenzenesulfonamide (23705-41-1)

Conditions	Yield
With sodium hypochlorite In water Ambient temperature;	99%

Cinnamyl acetate (21040-45-9) + sodium benzenesulfonate (873-55-2) → trans-cinnamyl phenyl sulfone (16212-07-0)

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; 1-ethyl-3-methylimidazolium tetrafluoroborate; palladium diacetate In water for 0.025h; Tsuji-Trost reaction; microwave irradiation;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium nitrite In N,N-dimethyl-formamide for 15h; Ambient temperature;	66%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 60℃; for 2h;

diphenyliodonium tetrafluoroborate + sodium benzenesulfonate (873-55-2) → iodobenzene (591-50-4) + diphenyl sulphone (127-63-9)

Conditions	Yield
In chloroform; water at 20℃; for 64h;	A n/a B 99%
In chloroform; water at 56℃; for 2.5h; Product distribution; other temperatures, other reaction time;	A 99 % Chromat. B 97%

sodium benzenesulfonate (873-55-2) + ethyl bromoacetate (105-36-2) → ethyl 2-phenylsulfonylacetate (7605-30-3)

Conditions	Yield
With aluminum oxide for 2h; Irradiation;	99%
In N,N-dimethyl-formamide for 3h;	95%
In ethanol for 3h; Heating;	86%

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 996-82-7 sodium diethylmalonate 
• 802869-23-4 benzenesulfonic acid N-phenyl-hydrazide 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 125556-92-5 2-Benzenesulfinyl-pyridine 1-oxide 
• 24040-12-8 2,4-dinitrophenyl benzenethiosulfonate 
• 141-97-9 ethyl acetoacetate 
• 94055-55-7 α-anthraquinonyl benzenethiosulfonate 
• 141-52-6 sodium ethanolate 
• 124-41-4 sodium methylate 
• 64-17-5 ethanol 
• 24244-60-8 2-(phenylsulfonyl)pyridine 
• 39574-20-4 2-benzenesulfonyl-pyridine N-oxide 

Downstream Products

• 65003-03-4 4-(2-(phenylsulfonyl)ethyl)pyridine 
• 4238-09-9 phenyl isopropyl sulfone 
• 5533-31-3 α-chlorobenzyl phenyl sulfone 
• 69267-28-3 benzenesulfonyl-malonic acid diethyl ester 
• 64345-00-2 2-(phenylsulfonyl)benzo[d]thiazole 
• 7205-98-3 chloromethyl phenyl sulfone 
• 599-94-0 1,2-bis(phenylsulfonyl)ethane 
• 98-11-3 benzenesulfonic acid 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 588-59-0 stilbene 
• 60-29-7 diethyl ether 
• 41037-77-8 4-(benzenesulfonyl-chloro-methyl)-benzonitrile 
• 38009-92-6 2-chloro-1-phenyl-2-(phenylsulfonyl)ethanone 
• 38377-19-4 1,2-bis-benzenesulfonyl-propane 

Relevant articles and documents

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.