4430-23-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3H-2,1-benzoxathiole 1,1-dioxide is utilized as a precursor in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Dye and Pigment Production:
This chemical compound serves as a building block in the production of dyes and pigments, playing a crucial role in the creation of colorants for different applications.
Used in Material Science:
3H-2,1-benzoxathiole 1,1-dioxide has applications in material science, particularly in the synthesis of polymers and resin composites, where its unique structure and reactivity contribute to the development of advanced materials with specific properties.

InChI:InChI=1/C7H6O3S/c8-11(9)7-4-2-1-3-6(7)5-10-11/h1-4H,5H2

Synthetic route

2-methylbenzene-1-sulfonyl fluoride (444-31-5) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
With sulfuric acid; fluorosulphonic acid; lead dioxide 1) -72 deg C, 6 h; Yield given. Multistep reaction;

by/at 79 degree melting o-sulfobenzoic acid dichloride → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
With hydrogenchloride; diethyl ether; zinc

chlorotolylsultone → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
With hydrogenchloride; zinc

sodium salt of/the/ benzaldehyde sulfonic acid-(2) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
With dimethyl sulfate

hydrogenchloride (7647-01-0) + diethyl ether (60-29-7) + 3,3-dichloro-3H-benz[c][1,2]oxathiol 1,1-dioxide (62574-72-5) + zinc → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
ebenso verlaeuft die Reduktion in neutraler Loesung mit Aluminiumamalgam oder die elektrolytische Reduktion;

2-iodomethyl-benzenesulfonyl fluoride (447-63-2) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + α-hydroxy-toluene-2-sulfonyl fluoride

Conditions	Yield
With ethanol; silver(l) oxide

ethanol (64-17-5) + 2-iodomethyl-benzenesulfonyl fluoride (447-63-2) + silver oxide → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + α-hydroxy-toluene-sulfonyl fluoride-(2)

α-iodo-toluene-sulfonyl fluoride-(2) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + 2-hydroxymethyl-benzenesulfonyl fluoride

Conditions	Yield
With ethanol; silver(l) oxide ein nicht einheitliches Praeparat;

potassium toluenesulfonate (143893-31-6) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + α-hydroxy-toluene-2-sulfonyl fluoride

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / FSO3H / 1 h / Ambient temperature 2: 1) PbO2, HSO3F, 2) 20percent aq. H2SO4 / 1) -72 deg C, 6 h View Scheme

sodium 2-formylbenzenesulfonate (1008-72-6) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate; phosphorus pentachloride / 1 h / 120 °C 2: hydrogenchloride; zinc / diethyl ether; water / 0.5 h / Heating View Scheme

3-chloro benzisoxathiole-1,1-dioxide (25595-59-9) → 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3)

Conditions	Yield
With hydrogenchloride; zinc In diethyl ether; water for 0.5h; Heating;	13.4 g

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + 4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]quinoline (583854-93-7) → 2-({4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}methyl)-1-benzenesulfonate (583854-88-0)

Conditions	Yield
at 120℃;	99%

2-Methylbenzothiazole (120-75-2) + 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → 2-methyl-3-(2-sulfobenzyl)benzothiazolium betaine

Conditions	Yield
at 150℃; for 4h; Alkylation;	78%

sodium cyanide (773837-37-9) + 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → sodium 2-(cyanomethyl)benzenesulfonate

Conditions	Yield
In ethanol; water for 4.33333h; Reflux;	72%

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + sodium butanolate (2372-45-4) → 2-butoxymethyl-benzenesulfonic acid

Conditions	Yield
With butan-1-ol

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + Sodium laurate (629-25-4) → 2-lauroyloxymethyl-benzenesulfonic acid

Conditions	Yield
at 135℃;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + sodium stearate (822-16-2) → 2-stearoyloxymethyl-benzenesulfonic acid

Conditions	Yield
With toluene

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + sodium phenylacetate (114-70-5) → 2-(phenylacetoxy-methyl)-benzenesulfonic acid

Conditions	Yield
at 135℃;
at 135℃;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + sodium butanolate (2372-45-4) + butan-1-ol (71-36-3) → 2-butoxymethyl-benzenesulfonic acid

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → 2-mercaptomethyl-benzenesulfonic acid

Conditions	Yield
With sodium hydrogensulfide at 125℃;

2-(1,3-dioxolan-2-yl)pyridine (5693-54-9) + 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → 2-[1,3]dioxolan-2-yl-1-(2-sulfo-benzyl)-pyridinium betaine (3340-21-4)

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + 1-(1,3-dioxolan-2-yl)isoquinoline (170486-98-3) → 1-[1,3]dioxolan-2-yl-2-(2-sulfo-benzyl)-isoquinolinium betaine (3340-27-0)

Conditions	Yield
In acetone

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + 2-(2-methyl-(1,3)-dioxolan-2-yl)pyridine (49669-15-0) → 2-(2-methyl-[1,3]dioxolan-2-yl)-1-(2-sulfo-benzyl)-pyridinium betaine (3340-19-0)

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + -metacresol (65135-15-1) → -metacresol purple

Conditions	Yield
With zinc(II) chloride at 105℃; for 15h; sealed tube; Yield given;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + diphenylphosphane (829-85-6) → Diphenyl-(2-kaliumsulfonatobenzyl)-phosphin (127324-81-6)

Conditions	Yield
With potassium tert-butylate 1) THF, 1.5 h, 25 deg C; 2) THF; Yield given. Multistep reaction;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + benzene (71-43-2) + sodium-compound of acetamide → α-acetylamino-toluene-2-sulfonic acid

methanol (67-56-1) + 3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → α-methoxy-toluene-2-sulfonic acid

Conditions	Yield
at 100℃; Kinetics;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + sodium hydrogensulfite → 2-mercaptomethyl-benzenesulfonic acid

Conditions	Yield
at 125℃;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + potassium hydroxide → ortho-cresol (95-48-7) + benzoic acid (65-85-0)

Conditions	Yield
beim Schmelzen;

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + alkali carbonate → benzyl alcohol-sulfonic acid-(2)

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) + alkali → benzyl alcohol-sulfonic acid-(2)

3H-benzo[c][1,2]oxathiole-1,1-dioxide (4430-23-3) → trans-2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecyn-16-yl)ethenyl]-3-(2-sulfobenzyl)benzothiazolium betaine (205388-75-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / 4 h / 150 °C 2: 65 percent / pyridine / 5 h / 90 °C View Scheme

Upstream product

• 444-31-5 2-methylbenzene-1-sulfonyl fluoride 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 62574-72-5 3,3-dichloro-3H-benz[c][1,2]oxathiol 1,1-dioxide 
• 447-63-2 2-iodomethyl-benzenesulfonyl fluoride 
• 64-17-5 ethanol 
• 143893-31-6 potassium toluenesulfonate 
• 1008-72-6 sodium 2-formylbenzenesulfonate 
• 25595-59-9 3-chloro benzisoxathiole-1,1-dioxide 

Downstream Products

• 127324-81-6 Diphenyl-(2-kaliumsulfonatobenzyl)-phosphin 
• 95-48-7 ortho-cresol 
• 65-85-0 benzoic acid 
• 1290573-54-4 2,2'-[(E)-ethene-1,2-diylbis(pyridinio-4,1-diylmethylene)]dibenzenesulfonate 

Relevant academic research and scientific papers

Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction

The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

OXIDATION OF METHYL-SUBSTITUTED BENZENESULFONYL FLUORIDES IN THE PbO2-HSO3F SYSTEM

The transformations of the sulfonyl fluorides of methyl-substituted benzenes in the PbO2-HSO3F system were studied.They take place through a stage involving the one-electron oxidation of the substrate to aromatic radical-cations.One of the transformation paths of the latter is realized through the elimination of a proton from the methyl groups involved to the greatest degree in the delocalization of the unpaired electron.This leads to the formation of diarylmethanes and the fluorosulfonates of substituted benzyl alcohols, which give substituted tolylsultones and benzyl alcohols during hydrolysis of the acid solution and methyl ethers of benzyl alcohols during methanolysis.The other path, which arises during localization of the unpaired electron in the unsubstituted positions of the benzene ring, leads to biaryls.