2634-33-5

Basic information

• Product Name: 1,2-Benzisothiazolin-3-one
• Synonyms: 1,2-benzisothiazoline-3-one;proxelpl;Proxan;proxel;Proxel XL;proxil;Benzisothiazolin-3-one;BIT
• CAS NO: 2634-33-5
• Molecular Formula: C₇H₅NOS
• Molecular Weight: 151.19
• EINECS: 220-120-9
• Product Categories: Volatiles/ Semivolatiles;chemical;Aromatics;Sulfur & Selenium Compounds;BA - BH;Beverage Standards;DIN and DL 152;European Community: ISO;Method Specific;Preservatives &A-B;Alpha Sort;Alphabetic;Analytical Standards;Analytical/Chromatography;Antioxidants;Building Blocks;C3 to C7;Chemical Synthesis;Chromatography;Environmental Standards;Food &Heterocyclic Building Blocks;Volatiles/ Semivolatiles;Preservative;Industrial/Fine Chemicals;Heterocycles;Sulphur Derivatives;Hydantoins & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks;Thiazoles;76/768/EEC;BA - BHChromatography;Preservatives&AntioxidantsBuilding Blocks;ThiazolesMethod Specific;A-BAlphabetic;Alpha Sort;B;European Community: ISO and DIN;Food&Beverage Standards
• Mol File: 2634-33-5.mol
• Article Data: 49

Chemical Properties

• Melting Point: 154-158 °C(lit.)
• Boiling Point: 360°C (rough estimate)
• Flash Point: 77.5 ºC
• Appearance: white to pale yellow powder
• Density: 1.2170 (rough estimate)
• Vapor Pressure: 0.183mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in dichloromethane, dimethyl sulfoxide, methanol.
• PKA: 10.19±0.20(Predicted)
• Water Solubility: 1.288g/L at 20℃
• CAS DataBase Reference: 1,2-Benzisothiazolin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzisothiazolin-3-one(2634-33-5)
• EPA Substance Registry System: 1,2-Benzisothiazolin-3-one(2634-33-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-38-41-43-50
• Safety Statements: 24-26-37/39-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: DE4620000
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2634-33-5(Hazardous Substances Data)

Usage

Description

BIT is an irritant and also a skin sensitizer. Occupational allergie contact dermatitis has been reported mainly related to the use of cutting oils and greases in paint manufacturers, pottery mouldmakers, acrylic emulsion manufacturers, plumbers, printers and lithoprinters, paper makers, an analyticallaboratory, a rubber factory, and in employees manufacturing air fresheners.

Chemical Properties

Yellow Powder

Uses

Different sources of media describe the Uses of 2634-33-5 differently. You can refer to the following data:
1. Antimicrobial agent.
2. Isothiazolinone BIT is widely used in industry as a preservative in water-based solutions, such as pastes, paints and cutting oils. It exists at different concentrations in the different Proxel AB, GXL, CRL, XL2, XL, HL, TN, and in Mergal K-10.
3. preservative in cooling fluids, paints, adhesives paper and in the textile industry

Application

1,2-benzisothiazol-3(2H)-one (BIT) has been widely used in high concentrations for microbial growth control in many domestic and industrial processes, its potential eco-risk should be assessed.

Definition

ChEBI: An organic heterobicyclic compound based on a fused 1,2-thiazole and benzene bicyclic ring skeleton, with the S atom positioned adjacent to one of the positions of ring fusion.

General Description

1,2-Benzisothiazol-3(2H)-one is a commonly used biocide in industrial and consumer products, which possesses antimicrobial activity against gram positive and gram negative bacteria. It is mainly used in packaging, adhesives, detergents, disinfectants, sunscreen lotions, paints and lubricants.

Flammability and Explosibility

Notclassified

Contact allergens

BIT, both an irritant and a skin sensitizer, is widely used in industry as a preservative in water-based solutions such as pastes, paints, and cutting oils. Occupational dermatitis has been reported mainly due to cutting fluids and greases, in paint manufacturers, pottery moldmakers, acrylic emulsions manufacturers, plumber,printers and lithoprinters, paper makers, analytical laboratory, rubber factory, and employees manufacturing air fresheners. It is also a preservative in vinyl gloves.

InChI:InChI=1/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)

Synthetic route

2-cyanothioanisole (6609-54-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
Stage #1: 2-cyanothioanisole With chlorine In water; chlorobenzene at 45 - 70℃; for 5h; Stage #2: With water; sodium hydroxide In chlorobenzene at 65 - 70℃; Concentration; Time;	99%
Stage #1: 2-cyanothioanisole With hydrogenchloride; water; chlorine In chlorobenzene at 45 - 70℃; for 3h; Stage #2: With water; sodium hydroxide In chlorobenzene at 65 - 70℃;	98%
Stage #1: 2-cyanothioanisole With chlorine In chlorobenzene at 40 - 80℃; Stage #2: With sodium hydroxide In water at 60 - 70℃; pH=10 - 12; Stage #3: With hydrogenchloride In water at 20 - 30℃; for 1h; pH=4 - 6;	90%

2-(dodecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 1-chlorododecane (112-52-7)

Conditions	Yield
With sulfuryl dichloride; water In chlorobenzene at 20 - 65℃; for 3h; Reagent/catalyst;	A 97.2% B 143 g
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h; Reagent/catalyst;

2-(dodecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 2-Chlorobenzonitrile (873-32-5) + 1-chlorododecane (112-52-7)

Conditions	Yield
Stage #1: 2-(dodecylthio)benzonitrile With sulfuryl dichloride; water In chlorobenzene at 20 - 65℃; for 3h; Stage #2: With sodium hydroxide In water at 60 - 65℃; pH=9 - 10; Stage #3: With hydrogenchloride In water at 20 - 30℃; pH=3 - 4; Reagent/catalyst;	A 106 g B 97.2% C 143 g

2-Chlorobenzonitrile (873-32-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
Stage #1: 2-Chlorobenzonitrile With tetrabutylammomium bromide; sodium thioethylate In water; chlorobenzene for 2h; Inert atmosphere; Reflux; Stage #2: With sulfuryl dichloride; water In chlorobenzene at 5 - 80℃; for 1h;	97%
Stage #1: 2-Chlorobenzonitrile With potassium carbonate; ethane-1,2-dithiol In 1,2-dichloro-ethane at 80℃; for 5h; Stage #2: With chlorine at 40 - 80℃; for 3h;	93.08%
With tetrabutylammomium bromide; sodium thiomethoxide at 70 - 80℃; for 0.666667h; Temperature; Reagent/catalyst;	92%

2,2 dithiobis(benzonitrile) (33174-74-2) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With oxygen; (tetracarboxyphalocyaninato)copper(II) In water at 40℃; under 4500.45 Torr; for 8h; Reagent/catalyst; Temperature; Pressure;	96%

2-cyanophenyl octyl sulfide (1160509-17-0) → 1,2-benzisothiazolin-3-one (2634-33-5) + 1-Chlorooctane (111-85-3)

Conditions	Yield
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;	A 94.5% B 100 g
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;

2-cyanophenyl octyl sulfide (1160509-17-0) → 1,2-benzisothiazolin-3-one (2634-33-5) + 2-Chlorobenzonitrile (873-32-5) + 1-Chlorooctane (111-85-3)

Conditions	Yield
Stage #1: 2-cyanophenyl octyl sulfide With water; chlorine In chlorobenzene at 20 - 65℃; for 3h; Stage #2: With sodium hydroxide In water at 60 - 65℃; pH=9 - 10; Stage #3: With hydrogenchloride In water at 20 - 30℃; pH=3 - 4;	A 103 g B 94.5% C 100 g

benzamide (55-21-0) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With oxygen; sodium thiosulfate; alpha cyclodextrin; iron(II) chloride In water at 40℃; Reagent/catalyst; Temperature;	94.5%

2-(octadecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;	A 93.5% B 210 g
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;

2-(octadecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 2-Chlorobenzonitrile (873-32-5) + 1-chlorooctadecane (3386-33-2)

Conditions	Yield
Stage #1: 2-(octadecylthio)benzonitrile With water; chlorine In chlorobenzene at 20 - 65℃; for 3h; Stage #2: With sodium hydroxide In water at 60 - 65℃; pH=9 - 10; Stage #3: With hydrogenchloride In water at 20 - 30℃; pH=3 - 4;	A 102 g B 93.5% C 210 g

2,2'-dithiobisbenzamide (2527-57-3) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With chlorine; potassium iodide In 1,2-dichloro-ethane at 25 - 40℃; for 0.416667h;	93%
With bromine In dichloromethane at 0 - 20℃;	53%
With sodium hydroxide

bis[2-(methoxycarbonyl)phenyl]disulfide (5459-63-2) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
Stage #1: bis[2-(methoxycarbonyl)phenyl]disulfide With acetamide; sodium methylate In toluene at 80℃; for 2h; Stage #2: With dihydrogen peroxide at 50 - 55℃; Stage #3: With hydrogenchloride at 25℃;	90%

2-methoxycarbonylbenzenesulfenamide (94266-24-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h; Cyclization;	87%

2-chlorosulfenylbenzoyl chloride (3950-02-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With ammonia In dichloromethane at -15 - 20℃; for 2h;	85%
With ammonia In 1,2-dichloro-ethane at 60℃; for 3h;	84%
With ammonium hydroxide
With ammonia In tetrachloromethane for 3h; Ambient temperature; Yield given;
With ammonium hydroxide In dichloromethane for 1h; Yield given;

2-methylsulfanyl-benzamide (54705-16-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With N-bromophthalimide In 1,1,2,2-tetrachloroethane at 50 - 60℃;	85%
With Selectfluor In acetonitrile at 80℃; for 12h; Schlenk technique; Sealed tube;	80%
With sulfuryl dichloride In toluene

Thiosalicylic acid (147-93-3) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With pyridine; diphenyl phosphoryl azide; triethylamine at 20℃; for 6h; Cyclization;	81%
Multi-step reaction with 2 steps 2: alcohol; ammonia gas View Scheme
Multi-step reaction with 2 steps 2: alcohol; ammonia gas View Scheme

o-aminoformylphenyl tert-butylsulfoxide → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
In toluene at 100℃; for 4h; Inert atmosphere;	81%

2-mercaptobenzamide (5697-20-1) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With dihydrogen peroxide In 1-methyl-pyrrolidin-2-one; water at 20℃; for 0.5h;	80.8%
With potassium hydroxide; hydroxylamine-O-sulfonic acid In methanol; water at 0℃; for 3h;	52%
Multi-step reaction with 2 steps 1: air 2: durch Bromieren in Tetrachlorkohlenstoff und Kochen des Reaktionsprodukts mit Eisessig View Scheme

2-chlorobenzamide (609-66-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
Stage #1: 2-chlorobenzamide With sodium sulfide In 1-methyl-pyrrolidin-2-one; water at 130 - 190℃; for 4h; Inert atmosphere; Stage #2: With dihydrogen peroxide In 1-methyl-pyrrolidin-2-one; water Temperature; Solvent;	80.8%
With carbon disulfide; L-proline; copper(I) bromide In dimethyl sulfoxide at 80℃; for 6h;	35%
Multi-step reaction with 2 steps 1: sodium sulfide hydrate / 1-methyl-pyrrolidin-2-one / 4 h / 160 °C 2: dihydrogen peroxide / 1-methyl-pyrrolidin-2-one; water / 0.5 h / 20 °C View Scheme

phenyl isocyanate (1197040-29-1) + o-aminoformylphenyl tert-butylsulfoxide → 2-(phenylamino)-4H-benzo[e][1,3]thiazin-4-one (15601-88-4) + 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
In toluene at 100℃; for 4h; Inert atmosphere;	A 79% B 5%

o-iodobenzamide (3930-83-4) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With carbon disulfide; L-proline; copper(I) bromide In dimethyl sulfoxide at 80℃; for 6h; Reagent/catalyst; Solvent; Temperature;	77%

methanol (67-56-1) + N-[(2-methoxycarbonylbenzene)sulfenyl]-1,2-benzisothiazolin-3-one (54856-20-1) → 1,2-benzisothiazolin-3-one (2634-33-5) + methyl 2-methoxycarbonylbenzenesulfenate

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 2.5h; Cyclization; alkoxylation;	A 34% B 71%

ethyl 2-sulfenamoylbenzoate (256947-56-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h; Cyclization;	69%

2-Bromobenzamide (4001-73-4) + potassium thioacyanate (333-20-0) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; 1,10-Phenanthroline; tetra-(n-butyl)ammonium iodide In water at 20 - 140℃; for 48.5h; Inert atmosphere;	60%

2-methoxycarbonylbenzenesulfenamide (94266-24-7) → 1,2-benzisothiazolin-3-one (2634-33-5) + bis[2-(methoxycarbonyl)phenyl]disulfide (5459-63-2) + N-2-methoxycarbonylphenylthio-2-methoxycarbonylbenzenesulfenamide (55255-14-6) + N-[(2-methoxycarbonylbenzene)sulfenyl]-1,2-benzisothiazolin-3-one (54856-20-1)

Conditions	Yield
In toluene at 100℃; for 5h; Cyclization;	A 23% B 13% C 5% D 58%

1-oxo-1H-1λ4-benzo[1,2]dithiol-3-one (66304-00-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With ammonia In dichloromethane for 1h; Ambient temperature;	55%

aniline (62-53-3) + 2-methoxycarbonylbenzenesulfenamide (94266-24-7) → 1,2-benzisothiazolin-3-one (2634-33-5) + methyl 2-(N-phenylsulfenamoyl)benzoate (34757-99-8)

Conditions	Yield
In toluene at 100℃; for 8h;	A 49% B 48%

2-Bromobenzamide (4001-73-4) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With carbon disulfide; L-proline; copper(I) bromide In dimethyl sulfoxide at 80℃; for 6h;	48%
Stage #1: 2-Bromobenzamide With sulfur; [2,2]bipyridinyl; copper(l) iodide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 24h; Inert atmosphere; Stage #2: With pyridine; N-methoxylamine hydrochloride In 1-methyl-pyrrolidin-2-one at 110℃; for 3h; Inert atmosphere;	15%

benzo[b]thieno[3,2-e]thiepino-4(10H)-one (3759-77-1) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
With sodium azide; sulfuric acid In dichloromethane for 72h; Ambient temperature;	45%

1,2-benzisothiazolin-3-one (2634-33-5) + tetramethyl ammoniumhydroxide (75-59-2) → tetramethylammonium 1,2-benzisothiazol-3-one (400089-65-8)

Conditions	Yield
In water pH=9.58;	100%
In water pH=9.0;

1,2-benzisothiazolin-3-one (2634-33-5) + 4-Methoxyphenyl isocyanate (5416-93-3) → N-(4-methoxyphenyl)benzisothiazol-3-one-2-amide (1423967-86-5)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	99%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-phenylethylisocyanate (14649-03-7, 33375-06-3, 65451-96-9, 1837-73-6) → N-(α-methylbenzyl)benzisothiazol-3-one-2-amide (1437999-75-1)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	99%

1,2-benzisothiazolin-3-one (2634-33-5) + 3-fluorobenzylisocyanate (102422-56-0) → N-(3-fluorobenzyl)benzisothiazol-3-one-2-amide (1438000-08-8)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	99%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-dodecylthiol (112-55-0) → 2-(dodecyldithio)benzamide

Conditions	Yield
In methanol at 20℃; for 0.5h;	98%

1,2-benzisothiazolin-3-one (2634-33-5) + benzyl isothiocyanate (3173-56-6) → 3-oxo-3H-benzo[d]isothiazole-2-carboxylic acid benzylamide

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	98%
In tetrahydrofuran at 45℃; for 1h;	88%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-Isocyanato-2-methoxy-benzene (700-87-8) → N-(2-methoxyphenyl)benzisothiazol-3-one-2-amide (1403613-12-6)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	98%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-Fluoro-2-isocyanato-benzene (16744-98-2) → N-(2-fluorophenyl)benzisothiazol-3-one-2-amide (1437999-29-5)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	98%

1,2-benzisothiazolin-3-one (2634-33-5) + 4-methoxybenzyl isocyanate (56651-60-6) → N-(4-methoxybenzyl)benzisothiazol-3-one-2-amide (1437999-95-5)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	98%

1,2-benzisothiazolin-3-one (2634-33-5) → sale sodico del 1,2-benzisotiazolin-3-one (58249-25-5)

Conditions	Yield
With sodium hydroxide In methanol at 50℃; for 1h;	98%
With sodium hydroxide In ethanol at 20℃; for 0.5h;	95%
With sodium hydroxide at 50℃;	92%
With sodium hydride In methanol for 2h; Reflux;

1,2-benzisothiazolin-3-one (2634-33-5) + n-butyl methanesulfonate (1912-32-9) → 2-butyl-1,2-benzothiazolin-3-one (4299-07-4)

Conditions	Yield
Stage #1: 1,2-benzisothiazolin-3-one With sodium methylate In methanol at 0℃; for 1h; Stage #2: n-butyl methanesulfonate In methanol for 6h; Temperature;	98%

1,2-benzisothiazolin-3-one (2634-33-5) + zinc(II) chloride (7646-85-7) → C14H10Cl2N2O2S2Zn

Conditions	Yield
In water; cyclohexanone at 95 - 156℃; Temperature; Solvent; Large scale;	97.6%

1,2-benzisothiazolin-3-one (2634-33-5) + methylene chloride (74-87-3) → 2-methyl-1,2-benzisothiazole-3(2H)-one (2527-66-4)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium iodide; sodium hydroxide In water at 30 - 100℃; Reagent/catalyst;	97.6%
Stage #1: 1,2-benzisothiazolin-3-one; methylene chloride In water at 20 - 30℃; for 1h; Stage #2: With sodium hydroxide In water at 60 - 70℃; pH=10 - 12;	124.4 g

1,2-benzisothiazolin-3-one (2634-33-5) + manganese(II) chloride tetrahydrate → C14H10Cl2MnN2O2S2

Conditions	Yield
In cyclohexanone at 95 - 156℃; Temperature; Solvent; Large scale;	97.5%

1,2-benzisothiazolin-3-one (2634-33-5) → 1,2-benzisothiazolin-3-one lithium salt

Conditions	Yield
With lithium hydroxide In ethanol at 80℃; for 2h;	97.4%
With lithium hydroxide monohydrate at 80℃; for 1.5h;	71.2%
With lithium hydroxide In methanol; water for 1h; Heating / reflux;

1,2-benzisothiazolin-3-one (2634-33-5) → 1,2-benzisothiazolin-3-one potassium salt (127553-58-6)

Conditions	Yield
With potassium hydroxide In acetic acid at 50℃; for 1h;	97.2%
With potassium hydroxide In water

1,2-benzisothiazolin-3-one (2634-33-5) + 3-methoxyphenyl isocyanate (18908-07-1) → N-(3-methoxyphenyl)benzisothiazol-3-one-2-amide (1437998-97-4)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	97%
In dichloromethane for 0.5h; Reflux;	88%

1,2-benzisothiazolin-3-one (2634-33-5) + para-fluorophenyl isocyanate (1195-45-5) → N-(4-fluorophenyl)benzisothiazol-3-one-2-amide (1437999-43-3)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	97%

1,2-benzisothiazolin-3-one (2634-33-5) + 4-chloro-3-(trifluoromethyl)phenyl isocyanate (327-78-6) → N-[4-chloro-3-(trifluoromethyl)phenyl]benzisothiazol-3-one-2-amide (1437999-63-7)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	97%

1,2-benzisothiazolin-3-one (2634-33-5) + 4-fluorobenzylisocyanate (132740-43-3) → N-(4-fluorobenzyl)benzisothiazol-3-one-2-amide (1438000-14-6)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	97%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-(isocyanatomethyl)-2-methoxybenzene (93489-08-8) → N-(2-methoxybenzyl)benzisothiazol-3-one-2-amide (1437999-81-9)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	96%

1,2-benzisothiazolin-3-one (2634-33-5) + 2-fluorobenzyl isocyanate → N-(2-fluorobenzyl)benzisothiazol-3-one-2-amide (1438000-02-2)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	96%

1,2-benzisothiazolin-3-one (2634-33-5) + phenyl isocyanate (103-71-9) → 3-oxo-N-phenylbenzo[d]isothiazole-2(3H)-carboxamide (51584-04-4)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	95%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-fluoro-3-isocyanatobenzene (404-71-7) → N-(3-fluorophenyl)benzisothiazol-3-one-2-amide (1437999-36-4)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	95%

1,2-benzisothiazolin-3-one (2634-33-5) + 1-(isocyanatomethyl)-3-methoxybenzene (57198-56-8) → N-(3-methoxybenzyl)benzisothiazol-3-one-2-amide (1437999-88-6)

Conditions	Yield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;	95%

Upstream product

• 34263-64-4 3-ethoxy-1,2-benzisothiazole 
• 94266-24-7 2-methoxycarbonylbenzenesulfenamide 
• 256947-56-5 ethyl 2-sulfenamoylbenzoate 
• 147-93-3 Thiosalicylic acid 
• 5459-63-2 bis[2-(methoxycarbonyl)phenyl]disulfide 
• 54705-16-7 2-methylsulfanyl-benzamide 
• 108-90-7 chlorobenzene 
• 56101-99-6 phenoxyethyl alcohol 
• 33441-56-4 ethyl 2-mercaptobenzoate 
• 5697-20-1 2-mercaptobenzamide 
• 62-53-3 aniline 
• 67-56-1 methanol 
• 54856-20-1 N-[2-(methoxycarbonyl)benzenesulfenyl]-1,2-benzisothiazolin-3-one 
• 66304-00-5 1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 

Downstream Products

• 101793-97-9 3-[5-(4-nitro-phenoxy)-pentyloxy]-benz[d]isothiazole 
• 100-47-0 benzonitrile 
• 26824-02-2 1-(2-mercaptophenyl)ethan-1-one 
• 2527-57-3 2,2'-dithiobisbenzamide 
• 1601403-11-5 N-(3-morpholinophenyl)-3-oxobenzo[d]isothiazole-2(3H)-carboxamide 
• 1601403-08-0 N-(2-morpholinophenyl)-3-oxobenzo[d]isothiazole-2(3H)-carboxamide 
• 1601403-53-5 N-(4-(1H-pyrrol-1-yl)phenyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 1601403-51-3 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(4-(pyridin-2-yl)phenyl)acetamide 
• 1601403-49-9 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(4-(piperidin-1-yl)phenyl)acetamide 

Relevant articles and documents

Novel palladium(II) and platinum(II) complexes of biocidal benzisothiazolinone (Bit); X-ray crystal structures of co-crystallised Bit/BitO and cis-Pd(en)(Bit-1H)2·H2O

Reaction of benzisothiazolinone (Bit), a well-known biocide, with the Pd(II) and Pt(II) am(m)ine precursors cis-[Pd(en)(H2O) 2](NO3)2 and cis-[Pt(NH3) 2(H2O)2](NO

Method for preparing 1, 2-benzisothiazolin-3-one through catalytic oxidation

The invention provides a method for preparing 1, 2-benzisothiazoline-3-one through catalytic oxidation, which comprises the following steps of: by taking a metal manganese salt or a manganese complex as a catalyst, carrying out oxidative cyclization react

Synthesis method of 1, 2-benzisothiazoline-3-ketone

The invention discloses a synthesis method of 1, 2-benzisothiazoline-3-ketone, which comprises the following steps: (1) adding 1, 2-dimercaptoethane and potassium carbonate at room temperature at one time, stirring, and slowly heating to obtain a mercapto

Bioisosteric investigation of ebselen: Synthesis and in vitro characterization of 1,2-benzisothiazol-3(2H)-one derivatives as potent New Delhi metallo-β-lactamase inhibitors

Carbapenem-resistant Enterobacteriaceae (CRE) producing New Delhi metallo-β-lactamase (NDM-1) cause untreatable bacterial infections, posing a significant threat to human health. In the present study, by employing the concept of bioisosteric replacement of the selenium moiety of ebselen, we have designed, synthesized and characterized a small compound library of 2-substituted 1,2-benzisothiazol-3(2H)-one derivatives and related compounds for evaluating their cytotoxicity and synergistic activity in combination with meropenem against the E. coli Tg1 (NDM-1) strain. The most promising compound 3a demonstrated potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE strains with FICI as low as 0.09. Moreover, its IC50 value and inhibition mechanism were also confirmed by using the enzyme inhibition assay and the ESI-MS analysis respectively. Importantly, compound 3a has acceptable toxicity and is not a PAINS. Because of its structural simplicity and potent synergistic activity in combination with meropenem, we propose that compound 3a may be a promising meropenem adjuvant and a new series of such compounds may worth further investigations.