136-95-8

Basic information

• Product Name: 2-Benzothiazolamine
• Synonyms: 2-Aminobenzthiazole;2-Iminobenzothiazoline;o-Aminobenzothiazole;u-Aminoben-zothiazole;USAF EK-3941;USAF xr-27;usafek-3941;usafxr-27
• CAS NO: 136-95-8
• Molecular Formula: C₇H₆N₂S
• Molecular Weight: 150.2
• EINECS: 205-268-4
• Product Categories: BENZOTHIAZOLE;Intermediates of Dyes and Pigments;Sulphur Derivatives;Heterocyclic Compounds;Metabolites & Impurities;Miscellaneous Reagents;Sulfur & Selenium Compounds;Metabolites & Impurities, Miscellaneous Reagents, Sulfur & Selenium Compounds
• Mol File: 136-95-8.mol
• Article Data: 128

Chemical Properties

• Melting Point: 126-129 °C(lit.)
• Boiling Point: 307.5 °C at 760 mmHg
• Flash Point: 139.8 °C
• Appearance: Beige to grayish/Powder or Flakes
• Density: 1.2162 (rough estimate)
• Vapor Pressure: 0.00331mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: -20°C
• Solubility: Soluble in alcohol, chloroform, diethyl ether.
• PKA: pK1: 4.48(+1) (20°C)
• Water Solubility: <0.1 g/100 mL at 19℃
• Merck: 14,424
• BRN: 116315
• CAS DataBase Reference: 2-Benzothiazolamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzothiazolamine(136-95-8)
• EPA Substance Registry System: 2-Benzothiazolamine(136-95-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• RTECS: DL1050000
• TSCA: Yes
• Hazardous Substances Data: 136-95-8(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE TO GREYISH POWDER OR FLAKES

Uses

Different sources of media describe the Uses of 136-95-8 differently. You can refer to the following data:
1. An impurity of pramipexole production
2. 2-Aminobenzothiazole was used in the synthesis of cobalt(II) picrate mixed-ligand complexes. It was used to study adsorption of biologically significant 2-aminobenzothiazole molecules on colloidal silver particles using surface-enhanced raman scattering spectroscopy
3. 2-Aminobenzothiazole was used in the synthesis of cobalt(II) picrate mixed-ligand complexes. It was used to study adsorption of biologically significant 2-aminobenzothiazole molecules on colloidal silver particles using surface-enhanced raman scattering spectroscopy.

General Description

Odorless gray to white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 2-Benzothiazolamine are not available; however, 2-Benzothiazolamine is probably combustible.

Biochem/physiol Actions

2-Aminobenzothiazole has local anaesthetic action and has numerous applications in human and veterinary medicine.

Purification Methods

The thiazole cystallises from a H2O, aqueous EtOH, *C6H6 or pet ether. The hydrochloride crystallises from dilute HCl and has m 240.5o. [Beilstein 27 H 182, 27 III/IV 4824.]

InChI:InChI=1/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2

Synthetic route

cyclohexanone (108-94-1) + thiourea (17356-08-0) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With dihydrogen peroxide; iodine; toluene-4-sulfonic acid In acetonitrile at 75℃; for 24h;	100%
With iodine; oxygen; toluene-4-sulfonic acid In dimethyl sulfoxide at 75℃; under 760.051 Torr; for 24h; Solvent; Reagent/catalyst;	84%

2-chlorobenzo[d][1,3]thiazole (615-20-3) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With 2-(di-1-adamantylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl; C58H78NO4PPdS; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; Inert atmosphere;	96%
With 5 wt% ruthenium/carbon; formamide; lithium tert-butoxide at 80℃; for 8h;	84%
With ammonia at 150 - 160℃;

monophenylthiourea (103-85-5) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With thionyl chloride at 50 - 55℃; for 4h;	95.6%
With bromine; acetic acid at 0 - 20℃; for 12h;	80%
Stage #1: monophenylthiourea With bromine In chloroform at 0 - 5℃; Reflux; Stage #2: With ammonia In water	75%

bromobenzene (108-86-1) + 2-iodophenylisothiourea → 2-amino-benzthiazole (136-95-8) + N-phenyl-2-benzothiazolamine (1843-21-6)

Conditions	Yield
With 1,10-Phenanthroline; copper(II) acetate monohydrate; caesium carbonate In dimethyl sulfoxide Heating;	A 95% B n/a
With 1,10-Phenanthroline; cobalt(II) sulfate monohydrate; caesium carbonate In dimethyl sulfoxide at 100℃; for 20h;

phenyl-carbamimidothioic acid (103-85-5) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
In isopropyl alcohol at 45℃; for 1.33333h; Temperature;	93%

2-nitrobenzothiazole (23505-64-8) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With triethylamine In water at 80℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;	92%

potassium thioacyanate (333-20-0) + aniline (62-53-3) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With bromine; acetic acid at 20℃; for 10h;	91%
Stage #1: potassium thioacyanate; aniline With acetic acid at 5℃; for 0.5h; Stage #2: With bromine; acetic acid at 0 - 20℃;	91%
With sodium iodide dichloride at 70℃; for 3h;	87%

ammonium thiocyanate (1147550-11-5) + aniline (62-53-3) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 10h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Irradiation;	90%
With bromine; acetic acid at 10℃;	88.5%
With bromine; acetic acid at 0 - 20℃;	74%

2-iodophenylamine (615-43-0) + thiourea (17356-08-0) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
bis(triethylphosphine)nickel(II) chloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 20h;	87%
bis(triethylphosphine)nickel(II) chloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 20h; Product distribution; other temp., other reaction time;	87%

2-bromo-1,3-benzothiazole (2516-40-7) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;	81%
With C24H32N2*ClCu; ammonia; potassium carbonate In 1-methyl-pyrrolidin-2-one; methanol at 90℃; under 5171.62 Torr; for 24h; Inert atmosphere;	73%
Stage #1: 2-bromo-1,3-benzothiazole With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.1h; Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; hexane; toluene at -30℃; for 2h; Inert atmosphere;	26%

ammonium thiocyanate + aniline (62-53-3) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
Stage #1: ammonium thiocyanate; aniline With acetic acid at 0℃; Stage #2: With bromine at -3 - 0℃;	75%
With bromine; acetic acid at 0 - 20℃;	74%
Stage #1: ammonium thiocyanate; aniline With acetic acid at 10℃; Stage #2: With bromine at 10 - 20℃; for 4h;	72%

2-amino-benzenethiol (137-07-5) + di(1H-imidazol-1-yl)methanimine (104619-51-4) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	71%

2-amino-benzenethiol (137-07-5) + ethyl cyanoformate (623-49-4) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With lithium bromide In 1,4-dioxane at 100 - 105℃; for 1h;	68%

1,3-Benzothiazole (95-16-9) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With sodium hydroxide; hydroxylamine hydrochloride at 100℃; for 3h;	63%
Stage #1: 1,3-Benzothiazole With lithium di-tert-butyl(2,2,6,6-tetramethylpiperidino)zincate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique; Stage #2: With N-benzyloxyamine; copper(l) cyanide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; regioselective reaction;	56%
Stage #1: 1,3-Benzothiazole With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -30℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;	26%

potassium sulphocyanide + aniline (62-53-3) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With bromine In acetic acid at 30℃; for 10h;	60%

copper(l) cyanide + 2-Aminophenyl disulfide (1141-88-4) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen In acetonitrile at 60℃; for 1h;	57%

2-iodophenylisothiourea → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With 1,10-Phenanthroline; iodobenzene; cobalt(II) sulfate monohydrate; caesium carbonate In dimethyl sulfoxide at 70℃; for 20h; Reagent/catalyst;	55%
With 1,10-Phenanthroline; copper(II) acetate monohydrate; caesium carbonate; chlorobenzene In dimethyl sulfoxide Heating;

benzothiazol-2-yl-lithium (39582-59-7) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With 1-azidostyrene In tetrahydrofuran for 2h; from -78 deg.C to room temp.;	53%

N-(2-chlorophenyl)thiazol-2-amine (136343-79-8) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With sodium hydroxide In water; tert-butyl alcohol for 29h; Irradiation;	47%

CYANAMID (420-04-2) + 2-amino-benzenethiol (137-07-5) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With zinc(II) acetate dihydrate In neat (no solvent) at 120℃; under 7600.51 Torr; for 18h; Autoclave; Inert atmosphere; Green chemistry;	45%

(E)-N-(1,3-benzothiazol-2-yl)-3-(thiophen-2-yl)acrylamide → 2-amino-benzthiazole (136-95-8) + 3-(2-thienyl)-2-propenoic acid (1124-65-8, 15690-25-2, 51019-83-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	A 43% B 32%

N-Cyclohexyl-2-phenylbenzo[d]imidazo[2,1-b]thiazol-3-amine → 2-amino-benzthiazole (136-95-8) + N-cicloesil-α-ossofenilacetamide (724-92-5)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 35%

2-(methylsulfonyl)aniline (2987-49-7) + thiourea (17356-08-0) → 2-amino-benzthiazole (136-95-8) + C7H9N3S*H(1+)

Conditions	Yield
In water; tert-butyl alcohol at 20 - 25℃; for 6h; Irradiation; DRL-400 mercury lamp (400 W);	A 34% B n/a

copper(l) cyanide + N,N'-(disulfanediylbis(2,1-phenylene))bis(4-methylbenzenesulfonamide) (3982-42-1) → 2-amino-benzthiazole (136-95-8) + C21H18N2O4S3

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In acetonitrile at 60℃;	A n/a B 23%

2-thioxo-3H-1,3-benzothiazole (149-30-4) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With ammonium hydroxide; ammonium bisulfite at 150℃;

2-nitrophenyl thiocyanate (2769-30-4) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With palladium on activated charcoal; acetic acid Hydrogenation;
With sulfuric acid bei der elektrolytischen Reduktion;
With hydrogenchloride; tin(ll) chloride
With ammonium hydroxide; iron(II) sulfate

(5-amino-[1,2,4]dithiazol-3-ylidene)-phenyl-amine (40229-47-8) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With hydrogenchloride at 165℃; im Rohr;

thiourea (17356-08-0) + 2-amino-benzenethiol (137-07-5) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
at 150℃;

1-phenyl-3-thiosemicarbazide (645-48-7) → 2-amino-benzthiazole (136-95-8)

Conditions	Yield
With hydrogenchloride at 125 - 130℃; im Rohr;

2-amino-benzthiazole (136-95-8) + methyl iodide (74-88-4) → 2-amino-3-methylbenzo[d]thiazol-3-ium iodide

Conditions	Yield
In acetonitrile at 45℃; for 12h;	100%
In acetonitrile at 45℃; for 12h;	100%
In N,N-dimethyl-formamide at 80℃; for 24h;	90%
In tetrahydrofuran at 20℃;

2-amino-benzthiazole (136-95-8) + iodobenzene (591-50-4) → N-(2-(phenylthio)phenyl)cyanamide (1201683-08-0)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline Alkaline conditions;	100%
With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 80℃; for 10h; Reagent/catalyst; Solvent; Inert atmosphere;	90%
With copper(ll) sulfate pentahydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h;

2-amino-benzthiazole (136-95-8) + 3-Methylbenzoyl chloride (1711-06-4) → N-(benzo[d]thiazol-2-yl)-3-methylbenzamide (200726-48-3)

Conditions	Yield
With pyridine at 60℃; for 16h; Inert atmosphere; Sealed tube;	100%
With pyridine at 60℃; for 16h;	90%

2-amino-benzthiazole (136-95-8) + trimethylsilyl cyanide (7677-24-9) + tert-butyl 3-formylpyrrolidine-1-carboxylate (59379-02-1) → tert-butyl 3-((benzo[d]thiazol-2-ylamino)(cyano)methyl)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: 2-amino-benzthiazole; tert-butyl 3-formylpyrrolidine-1-carboxylate With sodium sulfate In methanol at 20℃; for 24h; Stage #2: With acetic acid In methanol at 20℃; for 24h; Stage #3: trimethylsilyl cyanide With lithium perchlorate In tetrahydrofuran; phenol at 0 - 20℃; for 21h; Reflux;	100%

2-amino-benzthiazole (136-95-8) + 4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid (909262-73-3) → N-(1,3-benzothiazol-2-yl)-4-hydroxy-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	100%

2-amino-benzthiazole (136-95-8) + 1-(benzenesulphonyl)-4-hydroxypyrrolidine-2-carboxylic acid → 1-(benzenesulfonyl)-N-(1,3-benzothiazol-2-yl)-4-hydroxypyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	100%

2-amino-benzthiazole (136-95-8) + 1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid (88867-96-3) → N-(1,3-benzothiazol-2-yl)-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.98%

2-amino-benzthiazole (136-95-8) + L-N-tosyl-proline (51077-01-1, 110771-95-4) → N-(1,3-benzothiazol-2-yl)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.98%

2-amino-benzthiazole (136-95-8) + 4-hydroxy-1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid → N-(1,3-benzothiazol-2-yl)-4-hydroxy-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.96%

2-amino-benzthiazole (136-95-8) + C19H20N2O7S → N-(1,3-benzothiazol-2-yl)-3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]pentanamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.87%

2-amino-benzthiazole (136-95-8) + N-benzenesulfonyl-L-proline (88425-46-1) → 1-(benzenesulfonyl)-N-(1,3-benzothiazol-2-yl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.82%

2-amino-benzthiazole (136-95-8) + 3-(1H-indol-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]propanoic acid → N-(1,3-benzothiazol-2-yl)-3-(1H-indol-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]propanamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	99.33%

2-amino-benzthiazole (136-95-8) + chloroacetyl chloride (79-04-9) → N-benzothiazol-2-yl-2-chloroacetamide (3028-02-2)

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 20℃; for 1h;	99%
With potassium carbonate In chloroform for 10h; Reflux;	96%
Stage #1: 2-amino-benzthiazole With pyridine In benzene at 0 - 5℃; for 0.5h; Stage #2: chloroacetyl chloride In benzene for 2h;	95%

2-amino-benzthiazole (136-95-8) + 4-chlorobenzaldehyde (104-88-1) + β-naphthol (135-19-3) → 1-((benzo[d]thiazol-2-ylamino)(4-chloro-phenyl)methyl)naphthalen-2-ol

Conditions	Yield
With C5H14N2*BiCl5(2-)*2H(1+) In neat (no solvent) at 100℃; for 0.116667h;	99%
With 1. 2-pyrrolidon-1-ium hydrogen sulfate at 80℃; for 0.1h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Concentration; Green chemistry;	96%
With C12H28O3PS(1+)*Cl4Fe(1-) In neat (no solvent) at 45℃; for 0.05h; Ionic liquid; Green chemistry;	96%

2-amino-benzthiazole (136-95-8) + iodobenzene (591-50-4) → N-phenyl-2-benzothiazolamine (1843-21-6)

Conditions	Yield
With 1,10-Phenanthroline; copper(II) acetate monohydrate; caesium carbonate In dimethyl sulfoxide at 90℃; for 14h;	99%
With copper(l) iodide; potassium tert-butylate In 1,4-dioxane at 110℃; for 24h; Sealed tube;	91%
With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate In isopropyl alcohol at 80℃; for 4h; Ullmann Condensation;	83%

2-amino-benzthiazole (136-95-8) + para-Chlorobenzyl alcohol (873-76-7) → N‐(4‐chlorobenzyl)benzo[d]thiazol‐2‐amine

Conditions	Yield
With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh3)2]; potassium hydroxide In toluene at 100℃; for 12h; Reagent/catalyst;	99%
With cesium hydroxide; palladium diacetate In toluene at 150℃; for 12h;	98%
With C41H36AsClN3OPRuS; potassium hydroxide In toluene at 100℃; for 12h;	98%

2-amino-benzthiazole (136-95-8) + benzyl alcohol (100-51-6) → N-benzyl-2-aminobenzo[d]thiazole (21816-82-0)

Conditions	Yield
With C39H34CuN3P2S; potassium hydroxide In toluene at 100℃; for 12h; Catalytic behavior; Reagent/catalyst; regioselective reaction;	99%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; regioselective reaction;	97%
With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh3)2]; potassium hydroxide In toluene at 100℃; for 12h; Reagent/catalyst;	97%

2-amino-benzthiazole (136-95-8) + alpha-(3-methylphenoxy)acetophenone (19514-02-4) → 2- phenyl-3-(m-tolyloxy)benzo[d]imidazo[2,1-b]thiazole

Conditions	Yield
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h;	99%

2-amino-benzthiazole (136-95-8) + Monomethyl terephthalate (1679-64-7) → methyl 4-(benzo[d]thiazol-2-ylcarbamoyl)benzoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Sealed tube;	99%

2-amino-benzthiazole (136-95-8) + benzenesulfonyl chloride (98-09-9) → N-(benzo[d]thiazol-2-yl)benzenesulfonamide (13068-60-5)

Conditions	Yield
With pyridine for 1h; Heating;	98.9%
With pyridine at 0℃; for 2h; Inert atmosphere;	87%
In pyridine	52%
With pyridine

2-amino-benzthiazole (136-95-8) + 3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanoic acid → N-(1,3-benzothiazol-2-yl)-3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanamide

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux; Green chemistry;	98.66%

2-amino-benzthiazole (136-95-8) + ethyl acetoacetate (141-97-9) + 2-chloro-benzaldehyde (89-98-5) → 2-methyl-4-(2-chlorophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylic acid ethyl ester

Conditions	Yield
With Fe3O4(at)nano-cellulose/TiCl In neat (no solvent) at 70℃; for 0.666667h; Green chemistry;	98.5%
With nano-TiCl2/cellulose at 70℃; for 1h;	97%
With agar In ethanol; water for 1.08333h; Reflux; Green chemistry;	93%

2-amino-benzthiazole (136-95-8) + ethyl acetoacetate (141-97-9) + 4-chlorobenzaldehyde (104-88-1) → ethyl 4-(4-chlorophenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate (1360614-10-3)

Conditions	Yield
With Fe3O4(at)nano-cellulose/TiCl In neat (no solvent) at 70℃; for 0.666667h; Green chemistry;	98.5%
With nano-TiCl2/cellulose at 70℃; for 1h;	97%
With Cu(II) supported on nano-cellulose with Fe3O4 core In neat (no solvent) at 80℃; for 0.5h; Green chemistry;	95%

2-amino-benzthiazole (136-95-8) + benzoyl chloride (98-88-4) → N-(benzo[d]thiazol-2-yl)benzamide (5005-14-1)

Conditions	Yield
With pyridine for 12h;	98%
In pyridine	87%
In pyridine for 2h; Ambient temperature;	80%

2-amino-benzthiazole (136-95-8) + 2,5-hexanedione (110-13-4) → 1-(benzothiazol-2-yl)-2,5-dimethyl-1H-pyrrole (28142-87-2)

Conditions	Yield
montmorillonite K-10 at 90℃; for 0.1h; modified Paal-Knorr synthesis; microwave heating;	98%
With benzene
With toluene

2-amino-benzthiazole (136-95-8) + di-tert-butyl dicarbonate (24424-99-5) → 2-(tert-butoxycarbonylamino)benzo[d]thiazole

Conditions	Yield
With sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite In acetonitrile at 20℃; for 0.166667h; Neat (no solvent);	98%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 5.5h;	95%
With glycerol at 20℃; for 0.583333h; Green chemistry; chemoselective reaction;	93%

2-amino-benzthiazole (136-95-8) + ethyl acetoacetate (141-97-9) + 4-nitrobenzaldehdye (555-16-8) → ethyl 2-methyl-4-(4-nitrophenyl)-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate

Conditions	Yield
With Fe3O4(at)nano-cellulose/TiCl In neat (no solvent) at 70℃; for 0.666667h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Green chemistry;	98%
With nano-cellulose/BF3/Fe3O4 In neat (no solvent) at 100℃; for 0.75h; Green chemistry;	98%
With nano-kaolin/Ti4+/Fe3O4 In neat (no solvent) at 100℃; for 0.5h;	98%

2-amino-benzthiazole (136-95-8) + ethyl acetoacetate (141-97-9) + benzaldehyde (100-52-7) → ethyl 2-methyl-4-(phenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

Conditions	Yield
With Copper(II) supported graphene quantum dots modified NiFe2O4 nanoparticles In water at 20℃; for 0.666667h; Green chemistry;	98%
With nano-TiCl2/cellulose at 70℃; for 1h;	97%
With magnesium oxide In acetonitrile for 0.0833333h; Reflux;	95%

2-amino-benzthiazole (136-95-8) + ethyl acetoacetate (141-97-9) + 4-methoxy-benzaldehyde (123-11-5) → ethyl 2-methyl-4-(4-methoxyphenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

Conditions	Yield
With Copper(II) supported graphene quantum dots modified NiFe2O4 nanoparticles In water at 20℃; for 0.583333h; Green chemistry;	98%
With magnesium oxide In acetonitrile for 0.166667h; Reflux;	93%
With aminosulfonic acid In ethanol for 0.916667h; Reflux;	90%

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 2769-30-4 2-nitrophenyl thiocyanate 
• 14779-12-5 1,2-diimido-μ-disulfido-dicarbonic acid dianilide; dihydrobromide 
• 136343-79-8 N-(2-chlorophenyl)thiazol-2-amine 
• 615-43-0 2-iodophenylamine 
• 17356-08-0 thiourea 
• 2987-49-7 2-(methylsulfonyl)aniline 
• 62-53-3 aniline 
• 333-20-0 potassium thioacyanate 
• 16779-08-1 2-((benzo[d]thiazol-2-ylimino)methyl)phenol 
• 1147550-11-5 ammonium thiocyanate 
• 5005-14-1 N-(benzo[d]thiazol-2-yl)benzamide 
• 142-04-1 aniline hydrochloride 
• 14080-18-3 2-(pyrimidinylthio)benzene 

Downstream Products

• 4692-94-8 N-(1,3-benzothiazol-2-yl)-3-oxobutanamide 
• 73901-08-3 3-butyl-3H-benzothiazol-2-one-imine 
• 101317-85-5 bis-(3-methyl-benzothiazol-2-yl)-azamethinium ; toluene-4-sulfonate 
• 100537-65-3 3-[2]furyl-3-oxo-propionic acid benzothiazol-2-ylamide 
• 622803-37-6 6-chloro-pyridine-3-sulfonic acid benzothiazol-2-ylamide 
• 30937-73-6 2-(3-phenyl-triazenyl)-benzothiazole 
• 19412-20-5 N-benzothiazol-2-yl-N'-(4-nitro-phenyl)-triazene 
• 59548-35-5 3-benzothiazol-2-ylamino-isoindol-1-one 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 63123-39-7 acetylmercapto-acetic acid benzothiazol-2-ylamide 
• 101439-97-8 5-(benzothiazol-2-ylamino-methylene)-3-phenyl-2-thioxo-thiazolidin-4-one 
• 101727-77-9 4-nitro-trans-cinnamic acid benzothiazol-2-ylamide 
• 102452-52-8 N-(3-oxo-3-phenyl-propionyl)-sulfanilic acid benzothiazol-2-ylamide 
• 25829-71-4 3-hydroxy-[2]naphthoic acid benzothiazol-2-ylamide 

Relevant articles and documents

Discovery of Potent Carbonic Anhydrase Inhibitors as Effective Anticonvulsant Agents: Drug Design, Synthesis, and in Vitro and in Vivo Investigations

Two sets of benzenesulfonamide-based effective human carbonic anhydrase (hCA) inhibitors have been developed using the tail approach. The inhibitory action of these novel molecules was examined against four isoforms: HCA I, hCA II, hCA VII, and hCA XII. Most of the molecules disclosed low to medium nanomolar range inhibition against all tested isoforms. Some of the synthesized derivatives selectively inhibited the epilepsy-involved isoforms hCA II and hCA VII, showing low nanomolar affinity. The anticonvulsant activity of selected sulfonamides was assessed using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (sc-PTZ) in vivo models of epilepsy. These potent CA inhibitors effectively inhibited seizures in both epilepsy models. The most effective compounds showed long duration of action and abolished MES-induced seizures up to 6 h after drug administration. These sulfonamides were found to be orally active anticonvulsants, being nontoxic in neuronal cell lines and in animal models.

Synthesis and photophysical investigation of (BTHN) Schiff base as off-on Cd2+ fluorescent chemosensor and its live cell imaging

A Schiff base, 1-[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl-naphthalen-2-ol (BTHN) have been synthesized by the condensation of 2-hydrazinobenzothiazole and 2-hydroxy-1-naphthaldehyde. Structure of BTHN has been determined with the help of spectroscopic techniques and elemental analysis. Photophysical parameters of the BTHN were studied in the different solvents of varying polarity. The photophysical parameter were largely affected by the varying polarity and absorption as well as emission spectra showed strong bathochromic shift. Further, interactions of the BTHN dye with metal ions were also explored by spectrofluorimetry and BTHN found to be an excellent off-on chemosensor for Cd2+ in DMF-H2O solution. The molecular coordination complex between BTHN with Cd2+ is 1:1, confirmed by Benesi-Hildebrand and Job-plot method. In addition, the BTHN has been effectively employed for the fluorescence imaging of cadmium ions in the living cells.

Chemical Genetics Reveals a Role of Squalene Synthase in TGFβ Signaling and Cardiomyogenesis

KY02111 is a widely used small molecule that boosts cardiomyogenesis of the mesoderm cells derived from pluripotent stem cells, yet its molecular mechanism of action remains elusive. The present study resolves the initially perplexing effects of KY02111 on Wnt signaling and subsequently identifies squalene synthase (SQS) as a molecular target of KY02111 and its optimized version, KY-I. By disrupting the interaction of SQS with cardiac ER-membrane protein TMEM43, KY02111 impairs TGFβ signaling, but not Wnt signaling, and thereby recapitulates the clinical mutation of TMEM43 that causes arrhythmogenic right ventricular cardiomyopathy (ARVC), an inherited heart disease that involves a substitution of myocardium with fatty tissue. These findings reveal a heretofore undescribed role of SQS in TGFβ signaling and cardiomyogenesis. KY02111 may find its use in ARVC modeling as well as serve as a chemical tool for studying TGFβ/SMAD signaling.