4430-23-3

Basic information

• Product Name: 3H-2,1-benzoxathiole 1,1-dioxide
• Synonyms: 3H-2,1-benzoxathiole 1,1-dioxide;1,1-Dioxide-3H-2,1-benzoxathiole1,1-dioxide-3H-2,1-benzoxathiole1,1-dioxide-3H-2,1-benzoxathiole;1,1-DIOXIDE-3H-2,1-BENZOXATHIOLE;3H-benzo[c][1,2]oxathiole 1,1-dioxide;3H-benzo[c]oxathiole 1,1-dioxide;ALPHA-HYDROXY-O-TOLUENESULFONIC ACID GAMMA-SULTONE
• CAS NO: 4430-23-3
• Molecular Formula: C₇H₆O₃S
• Molecular Weight: 170.18574
• EINECS: 224-620-8
• Mol File: 4430-23-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 310.7 °C at 760 mmHg
• Flash Point: 141.7 °C
• Appearance: /
• Density: 1.465 g/cm³
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 3H-2,1-benzoxathiole 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-2,1-benzoxathiole 1,1-dioxide(4430-23-3)
• EPA Substance Registry System: 3H-2,1-benzoxathiole 1,1-dioxide(4430-23-3)

Safety Data

• Hazardous Substances Data: 4430-23-3(Hazardous Substances Data)

Usage

General Description

3H-2,1-benzoxathiole 1,1-dioxide, also known as dibenzothiophene dioxide, is a chemical compound with the molecular formula C12H8O2S. It is a heterocyclic organic compound containing both sulfur and oxygen atoms in a six-membered ring structure. 3H-2,1-benzoxathiole 1,1-dioxide is commonly used as a precursor in the synthesis of pharmaceuticals and agrochemicals. It is also used as a building block in the production of dyes and pigments. Additionally, dibenzothiophene dioxide has applications in the field of material science, where it is utilized in the synthesis of polymers and resin composites. Overall, this chemical compound has a wide range of industrial and scientific applications due to its unique molecular structure and reactivity.

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

• 25595-59-9 3-chloro benzisoxathiole-1,1-dioxide 
• 1008-72-6 sodium 2-formylbenzenesulfonate 
• 143893-31-6 potassium toluenesulfonate 
• 64-17-5 ethanol 
• 447-63-2 2-iodomethyl-benzenesulfonyl 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 
• 444-31-5 2-methylbenzene-1-sulfonyl fluoride 

Relevant articles and documents

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.