27148-03-4

Basic information

• Product Name: 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide
• Synonyms: 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide;Thiosaccharin;1,2-benzisothiazol-3-(2H)-thione-1,1-dioxide;Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide;1,2-benzisothiazole-3-thiol 1,1-dioxide
• CAS NO: 27148-03-4
• Molecular Formula: C₇H₅NO₂S₂
• Molecular Weight: 199.2501
• Mol File: 27148-03-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 192 °C
• Boiling Point: 379°Cat760mmHg
• Flash Point: 183°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 6.05E-06mmHg at 25°C
• Refractive Index: 1.748
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.89±0.20(Predicted)
• CAS DataBase Reference: 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide(27148-03-4)
• EPA Substance Registry System: 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide(27148-03-4)

Safety Data

• Hazardous Substances Data: 27148-03-4(Hazardous Substances Data)

Usage

General Description

1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide is a chemical compound that contains a benzisothiazole ring with a thione and dioxide functional group. It is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide is also known for its antimicrobial and fungicidal properties, making it useful in the production of antimicrobial coatings and materials. Additionally, 1,2-Benzisothiazole-3(2H)-thione 1,1-dioxide has potential applications in the treatment of certain medical conditions, such as epilepsy and neurodegenerative diseases. Overall, this chemical compound has a range of important industrial and medicinal uses due to its unique chemical structure and properties.

InChI:InChI=1/C7H5NO2S2/c9-12(10)6-4-2-1-3-5(6)7(11)8-12/h1-4H,(H,8,11)

Synthetic route

saccharin (81-07-2) → thiosaccharine (27148-03-4)

Conditions	Yield
With tetraphosphorus decasulfide at 50 - 170℃;	75%
With diphosphorus pentasulfide at 180 - 220℃;
With tetraphosphorus decasulfide

thiosaccharine (27148-03-4) → 3-hydrazinosaccharin

Conditions	Yield
With hydrazine hydrate In ethanol for 0.5h; Heating;	91.9%

thiosaccharine (27148-03-4) + dichloro(bis(diphenylphosphino)methane)platinum(II) (52595-94-5) → C39H30N2O4P2PtS4*0.5CHCl3

Conditions	Yield
With triethylamine In chloroform for 1h; Reflux;	91%

thiosaccharine (27148-03-4) + zinc(II) nitrate hexahydrate + 2,2'-biquinoline (119-91-5) → 2C7H4NO2S2(1-)*Zn(2+)*C18H12N2

Conditions	Yield
Stage #1: thiosaccharine; zinc(II) nitrate hexahydrate In ethanol; water Stage #2: 2,2'-biquinoline In ethanol; water	90%

thiosaccharine (27148-03-4) + bis[(benzyldimethylamino)chloropalladium(II)] → C25H28ClN3O2Pd2S2

Conditions	Yield
In methanol; chloroform at 20℃; for 2h;	90%

cisplatin (15663-27-1) + thiosaccharine (27148-03-4) → cis-[Pt(II)(thiosaccharinate)2(NH3)2]

Conditions	Yield
In water for 2h; Reflux;	89%

[2,2]bipyridinyl (366-18-7) + thiosaccharine (27148-03-4) + zinc(II) nitrate hexahydrate → 2C7H4NO2S2(1-)*Zn(2+)*C10H8N2

Conditions	Yield
Stage #1: thiosaccharine; zinc(II) nitrate hexahydrate In ethanol; water Stage #2: [2,2]bipyridinyl In ethanol; water	85%

thiosaccharine (27148-03-4) + [1,3-bis(diphenylphosphino)propane]dichloroplatinum(II) (59329-00-9) → C41H34N2O4P2PtS4 (1429789-37-6)

Conditions	Yield
With triethylamine In chloroform for 1h; Reflux;	82%

thiosaccharine (27148-03-4) + zinc(II) nitrate hexahydrate + 1,3-di(4-pyridyl)propane (17252-51-6) → [Zn(1,1-dioxo-1,2-benzisothiazole-3-thiolato)2(4,4'-trimethylenedipyridine)]n

Conditions	Yield
In ethanol; water at 20℃;	82%

thiosaccharine (27148-03-4) + [platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)] (83095-83-4, 14647-25-7) → C40H32N2O4P2PtS4*CH2Cl2

Conditions	Yield
With triethylamine In chloroform for 1h; Reflux;	81%

thiosaccharine (27148-03-4) + (1,4-bis(diphenylphosphanyl)butane)dichloridoplatinum(II) (65097-96-3) → C42H36N2O4P2PtS4 (1429789-52-5)

Conditions	Yield
With triethylamine In chloroform for 1h; Reflux;	80%

thiosaccharine (27148-03-4) + [Pd(benzisothiazolinate)2]*H2O → [Pd(benzisothiazolinate)(thiosaccharin)]

Conditions	Yield
In methanol; chloroform for 3.16667h;	79%

thiosaccharine (27148-03-4) + bis(acetylacetonato)palladium(II) → palladium(II) thiosaccharinate

Conditions	Yield
In acetonitrile dropwise addn. of thiosaccharine in MeCN to MeCN soln. of Pd(acac)2 at room temp. on dry air; filtered; washed with MeCN and Et2O; dried on air; elem. anal.;	76%

thiosaccharine (27148-03-4) + bismuth(III) tert-butoxide → bismuth tris(thiosaccharinate)

Conditions	Yield
In tetrahydrofuran byproducts: t-BuOH; under N2; thiosaccharine added to soln. of Bi(O-t-Bu)3 (molar ratio 3:1)in dried THF at -80°C; stirred overnight; volatiles removed under vac.; washed with EtOH; elem. anal.;	75%

thiosaccharine (27148-03-4) → C14H8N2O4S4 (1416047-04-5)

Conditions	Yield
With potassium permanganate In water	75%

thiosaccharine (27148-03-4) + trans-Cl2Pd(H2NCH2C6H5)2 (19046-92-5, 55176-74-4) → trans-[Pd(S-thiosaccharinate )2(benzylamine)2]

Conditions	Yield
In methanol at 30℃; for 2h;	75%

1,10-Phenanthroline (66-71-7) + thiosaccharine (27148-03-4) + zinc(II) nitrate hexahydrate → [Zn(1,1-dioxo-1,2-benzisothiazole-3-thiolato)2(o-phenantroline)]

Conditions	Yield
Stage #1: thiosaccharine; zinc(II) nitrate hexahydrate In ethanol; water Stage #2: 1,10-Phenanthroline In ethanol; water	74%

thiosaccharine (27148-03-4) + triphenylbismuthane (603-33-8) → phenylbismuth bis(thiosaccharinate)

Conditions	Yield
In ethanol byproducts: benzene; mixt. of BiPh3 and thiosaccharine (molar ratio 1:2) in EtOH refluxed for1 h; volatiles removed under vac.; washed with toluene; elem. anal.;	73%

thiosaccharine (27148-03-4) + silver nitrate → poly[(μ3-1,1-dioxo-1,2-benzoisothiazole-3-thiolato-κ(3)N:S(3):S(3))silver(I)]

Conditions	Yield
In acetonitrile reaction of AgNO3 with ligand in acetonitrile; recrystn. (acetonitrile);	71%
In acetonitrile soln. of AgNO3 in MeCN added to MeCN of tiosaccharin with mechanical stirring at room temp.; solid filtered off; washed with diethyl ether; dissolved in DMSO; CH2Cl2slowly diffused;

potassium tetrachloroplatinate(II) (10025-99-7) + thiosaccharine (27148-03-4) → 2C7H4NO2S2(1-)*Pt(2+)*H2O

Conditions	Yield
In methanol; water for 2h; Reflux;	71%

thiosaccharine (27148-03-4) + C16H12N2O10Os3 → C17H5NO12Os3S2 + C17H5NO12Os3S2

Conditions	Yield
In benzene at 20℃; for 2h; Inert atmosphere; Schlenk technique;	A 68% B 22%

thiosaccharine (27148-03-4) + thallium chloride → thallium(I) thiosaccharinate

Conditions	Yield
In water 1 equiv. of aq. soln. of TlCl was added to aq. soln. of S-compd. under stirring; solid was filtered off, washed with cold H2O, dried over CaCl2;	65%

thiosaccharine (27148-03-4) + dichloro(bis(diphenylphosphino)methane)platinum(II) (52595-94-5) → C64H52N2O4P4PtS4*0.5CH2Cl2

Conditions	Yield
With triethylamine In chloroform for 1h; Reflux;	65%

[2,2]bipyridinyl (366-18-7) + thiosaccharine (27148-03-4) + silver nitrate → bis(2,2'-bipyridine)bis-μ2-S-(thiosaccharinato)-disilver(I) (954103-47-0)

Conditions	Yield
In acetonitrile slow addn. of a soln. of ligand in acetonitrile to a soln. of silver salt and bipyridine in acetonitrile, standing at room temp. in the dark for1 d; elem. anal.;	55%

thiosaccharine (27148-03-4) + chloroacetonitrile (107-14-2) → (1,1-dioxo-1H-1λ6-benzo[d]isothiazol-3-ylsulfanyl)-acetonitrile (80357-08-0)

Conditions	Yield
Stage #1: thiosaccharine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: chloroacetonitrile In N,N-dimethyl-formamide for 10h; Heating;	50%

thiosaccharine (27148-03-4) + triphenylbismuthane (603-33-8) → diphenylbismuth(III) thiosaccharinate

Conditions	Yield
In ethanol byproducts: benzene; mixt. of BiPh3 and thiosaccharine (molar ratio 1:1) in EtOH refluxed for30 min; volatiles removed under vac.; washed with toluene; recrystd. from EtOH; elem. anal.;	50%

thiosaccharine (27148-03-4) + bis(acetylacetonato)palladium(II) + triphenylphosphine (603-35-0) + acetonitrile (75-05-8) → bis(thiosaccharinato)bis(triphenylphosphane)palladium(II)monoacetonitrile (1223048-87-0)

Conditions	Yield
In acetonitrile PPh3 added to MeCN soln. of Pd(acac)2; stirred for 1 h at 40°C; MeCN soln. of thiosaccharin added; stirred for 1 h; filtered; washed with MeCN and Et2O; dried on air; elem. anal.;	47%

pyridine (110-86-1) + thiosaccharine (27148-03-4) + silver nitrate → pyridine-bis(μ2-S:N-(1,1-dioxide-1,2-benzoisothiazol-3-thionato-κ2S:N)silver(I)) (1055310-56-9)

Conditions	Yield
In pyridine; acetonitrile addn. of CH3CN soln. of thiosaccharin to pyridine soln. of silver nitrate; filration, washing with diethyl ether, elem. anal.;	42%

thiosaccharine (27148-03-4) + ethanol (64-17-5) + gold(III) chloride (13453-07-1) + bis-diphenylphosphinomethane (2071-20-7) → μ-bis(diphenylphosphino)methane-κP,P'-bis[(1,1-dioxide-1,2-benzoisothiazol-3-thionato-κS) gold(I)] solvato ethanol (1340587-84-9)

Conditions	Yield
In ethanol EtOH soln. of PPh3 warmed at 45°C; AuCl3 in EtOH added dropwise; soln. kept under stirring; EtOH soln. of thiosaccharin added; solvent slowly evapd. for 24 h; crystals washed with Et2O; air dried; elem. anal.;	34%

thiosaccharine (27148-03-4) + ethanol (64-17-5) + gold(III) chloride (13453-07-1) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → μ-bis(diphenylphosphino)ethane-κP,P'-bis[(1,1-dioxide-1,2-benzoisothiazol-3-thionato-κS) gold(I)] solvato ethanol

Conditions	Yield
In ethanol EtOH soln. of PPh3 warmed at 45°C; AuCl3 in EtOH added dropwise; soln. kept under stirring; EtOH soln. of thiosaccharin added; solvent slowly evapd. for 24 h; crystals washed with Et2O; air dried; elem. anal.;	34%

Upstream product

• 81-07-2 saccharin 

Downstream Products

• 61766-82-3 3-(methylthio)-1,2-benzisothiazole 1,1-dioxide 
• 936-16-3 2,3-dihydro-1,2-benzisothiazole 1,1-dioxide 
• 632-24-6 2-sulfamoyl-benzoic acid 
• 81-07-2 saccharin 
• 80357-08-0 (1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-ylsulfanyl)-acetonitrile 
• 1223048-96-1 bis(thiosaccharinato)bis[bis(diphenylphosphanyl)methane]palladium(II) 
• 1223048-87-0 bis(thiosaccharinato)bis(triphenylphosphane)palladium(II)monoacetonitrile 
• 1223049-00-0 bis(thiosaccharinato)[bis(diphenylphosphanyl)ethane]palladium(II) monoacetonitrile 
• 1340587-84-9 μ-bis(diphenylphosphino)methane-κP,P'-bis[(1,1-dioxide-1,2-benzoisothiazol-3-thionato-κS) gold(I)] solvato ethanol 
• 1340587-82-7 (1,1-dioxide-1,2-benzoisothiazol-3-thionato-κS)triphenylphosphinegold(I) 
• 954103-46-9 tris(triphenylphosphine)-η1-S-(thiosaccharinato)silver(I) 
• 1223048-91-6 bis(thiosaccharinato)[bis(diphenylphosphanyl)methane]palladium(II) 
• 1429789-37-6 C₄₁H₃₄N₂O₄P₂PtS₄ 

Relevant articles and documents

Zn thiosacharinates: From ionic to polymeric structures. Synthesis, characterization and cell proliferation inhibition studies

A series of Zn thiosacharinates complexes with nitrogen donor co-ligands were synthesized: [Zn(tsac)2(o-phen)], [Zn(tsac)2(TMDP)]n, [(4,4′-bipy)H2][Zn(tsac)4] [Zn(tsac)2(2,2′-bipy)], [Zn(tsac)2(2,2′-bquin)], (tsac, thiosaccharinate anion: 1,1-dioxo-1,2-benzisothiazole-3-thiolato, C7H4NO2S2?, o-phen: 1,10′-phenantroline, TMDP: trimethylenedipyridine, 2,2′-bipy: 2,2′-bipyridine, 4,4′-bipy: 4,4′-bipyridine, 2,2′-bquin: 2,2′-biquinoline). They were fully characterized by means of FTIR, 13C and 1H NMR, elemental analysis and conductivity measurements. Three of them, [Zn(tsac)2(o-phen)], [(4,4′-bipy)H2][Zn(tsac)4], [Zn(tsac)2(TMDP)]n were also characterized by X-ray single crystal diffractometry and their crystal structures are described herein. DFT geometry optimization for the [Zn(tsac)2(o-phen)] complex was performed and its vibrational spectra was predicted. Moreover, we studied the effects of the five complexes on cell proliferation, thus providing preliminary evidence for their therapeutic potential as anti-cancer drugs.

Structural study of thiosaccharin by single crystal X-ray diffraction and infrared spectroscopy

The structure of thiosaccharin (1,2-benzisothiazol-3(2H)-thione 1,1-dioxide) has been investigated by X-ray diffraction and infrared spectroscopic methods.The compound crystallizes in the orthorhombic space group Fdd2 with a = 26.591(3), b = 25.058(3), c = 4.934(5) Angstroem, Z = 16.The structure consists of thiosaccharin molecules bonded to each other through N-HO intermolecular hydrogen bonds.The infrared spectra of the thiosaccharin at room and liquid-nitrogen temperature were recorded.The spectral features in the N-H stretching region were correlated with the crystallographic data on the geometry of the N-HO hydrogen bonding.In an attempt to assign the bands due to the SO2 stretching modes, the spectrum of thiosaccharin was compared with that of saccharin (1,2-benzoisothiazole-3(2H)-one, 1,1-dioxide.KEY WORDS: Thiosaccharin, infrared spectra, crystal structure polymorphs.

Pseudosaccharin amine derivatives: Synthesis and elastase inhibitory activity

Pseudosaccharin amines were synthesized from saccharin either by the reaction of pseudosaccharin chloride with amines, or via thiosaccharin which was treated with amines yielding thiosaccharinates, and their reaction with glacial acetic acid. This route gave lower yields than the first way. The synthesis of alkyl [(1,1-dioxo-benzo[d]isothiazol-3-yl)amino]alkanoates as possible Human Leukocyte Elastase (HLE) inhibitors was realized by the reaction between amino acid esters and pseudosaccharin chloride. Hydrolysis of the esters was possible under aqueous basic conditions. Selected compounds were screened for elastase inhibitory activity. Compounds 4k and 4m were found to be reversible inhibitors of HLE with Ki values of 45 μM and 60 μM.