95-24-9

Basic information

• Product Name: 2-Amino-6-chlorobenzothiazole
• Synonyms: 2-amino-6-chloro-benzothiazol;2-Benzothiazolamine, 6-chloro-;6-chloro-2-benzothiazolamin;Benzothiazole, 2-amino-6-chloro-;LABOTEST-BB LT00012588;IFLAB-BB F1386-0399;2-AMINO-6-CHLOROBENZOTHIAZOLE;6-CHLORO-BENZOTHIAZOL-2-YLAMINE
• CAS NO: 95-24-9
• Molecular Formula: C₇H₅ClN₂S
• Molecular Weight: 184.65
• EINECS: 202-402-3
• Product Categories: Intermediates of Dyes and Pigments;BENZOTHIAZOLE;Sulphur Derivatives;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks
• Mol File: 95-24-9.mol
• Article Data: 99

Chemical Properties

• Melting Point: 199-201 °C(lit.)
• Boiling Point: 344.3 ºC at 760 mmHg
• Flash Point: 162 ºC
• Appearance: Off-white to light beige/Crystalline Powder
• Density: 1.4750 (rough estimate)
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 3.30±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-chlorobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-chlorobenzothiazole(95-24-9)
• EPA Substance Registry System: 2-Amino-6-chlorobenzothiazole(95-24-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: DL1575000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 95-24-9(Hazardous Substances Data)

Usage

General Description

2-amino-6-chloro-benzothiazole on microwave irradiation in the presence of 1-butyl-3-methylimidazolium and inorganic anions yields fluorinated benzothiazolo[2,3-b]quinazoline-2H-ones analogues. It has synergistic effect on inhibitive performance of propargyl alcohol during corrosion of mild steel in boiling HCl solution.

InChI:InChI=1/C7H5ClN2S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H2,9,10)

Upstream product

• 103-85-5 monophenylthiourea 
• 106-47-8 4-chloro-aniline 
• 7647-01-0 hydrogenchloride 
• 136-95-8 2-amino-benzthiazole 
• 2942-10-1 6-chloro-1,3-benzothiazole 
• 3425-46-5 potassium selenocyanate 
• 20265-96-7 p-chloroaniline hydrochloride 
• 333-20-0 potassium thioacyanate 
• 62-53-3 aniline 
• 1280582-67-3 4-chloro-2-thiocyanatoaniline 
• 1367199-79-8 BrH*C₇H₅ClN₂S 
• 7758-99-8 copper(II) sulfate 
• 67-56-1 methanol 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 103028-29-1 2-bromo-propionic acid-(6-chloro-benzothiazol-2-ylamide) 
• 1819-51-8 N-phenyl-N'-(6-chloro)benzothiazolylthiocarbamide 
• 58199-49-8 6-chloro-3-methyl-3H-benzothiazol-2-ylideneamine 
• 34551-19-4 6-chloro-N-methylbenzo[d]thiazol-2-amine 
• 842161-89-1 2-(p-acetylaminobenzenesulfonylamino)-6-chlorobenzothiazole 
• 3268-75-5 2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide 
• 3622-23-9 2,6-dichloro-1,3-benzothiazole 
• 855282-75-6 2-chloro-6-iodobenzothiazole 
• 38338-20-4 2-amino-4-bromo-6-chlorobenzo[d]thiazole 
• 30459-51-9 6-Chlor-3-ethylbenzothiazol-2-on 
• 93567-34-1 4-chloro-N-(6-chloro-benzothiazol-2-yl)-3-sulfamoyl-benzamide 
• 3718-97-6 N-(6-chlorobenzothiazole-2-yl)-2-(2,5-dimethoxyphenyl)acetamide 
• 3719-05-9 2-(2-(3,4-dimethoxyphenyl)acetamido)-6-chlorobenzothiazole 
• 56311-83-2 (6-chloro-benzothiazol-2-yl)-(4-chloro-benzylidene)-amine 

Relevant articles and documents

Novel benzothiazole hydrazine carboxamide hybrid scaffolds as potential in vitro GABA AT enzyme inhibitors: Synthesis, molecular docking and antiepileptic evaluation

In the present study, a series of newer benzothiazole derivatives containing thiazolidin-4-one (5a-g) and azetidin-2-one (6a-g), were synthesized by the cyclization of benzothiazolyl arylidene hydrazine carboxamide derivatives with thioglycolic acid and chloroacetyl chloride, respectively. Results of in vivo anticonvulsant screening revealed that compounds having 2,4-dicholoro (5c and 6c) and 4-nitro substituent (5g) at the phenyl ring have promising anticonvulsant activities without any neurotoxicity. Selected compounds were also evaluated for their in vitro GABA AT inhibition. The results indicated that compound 5c (IC50 15.26 μM) exhibited excellent activity as compared to the standard drug vigabatrin (IC50 39.72 μM) suggesting the potential of these benzothiazole analogues as new anticonvulsant agents.

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O

Treatment of a variety of substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F) were well tolerated. This method provides a useful alternative to other methods that are either less efficient (requiring 3–7 fold equivalents of reagents) or utilize highly toxic and corrosive liquid Br2 as the oxidizing agent.