21816-82-0

Basic information

• Product Name: N-Benzylbenzothiazole-2-amine
• Synonyms: N-Benzyl-2-benzothiazolamine;N-Benzylbenzothiazole-2-amine
• CAS NO: 21816-82-0
• Molecular Formula: C₁₄H₁₂N₂S
• Molecular Weight: 240.33
• Mol File: 21816-82-0.mol
• Article Data: 61

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Benzylbenzothiazole-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylbenzothiazole-2-amine(21816-82-0)
• EPA Substance Registry System: N-Benzylbenzothiazole-2-amine(21816-82-0)

Safety Data

• Hazardous Substances Data: 21816-82-0(Hazardous Substances Data)

Upstream product

• 50506-90-6 4-benzyl-2-phenyl-5-phenylimino-[1,2,4]thiadiazolidine-3-thione 
• 1028454-88-7 α-(diphenylphosphoryl)methyl 2-benzothiazolylsulfoxide 
• 100-46-9 benzylamine 
• 797763-25-8 α-(diethoxyphosphoryl)methyl 2-benzothiazolylsulfoxide 
• 615-43-0 2-iodophenylamine 
• 622-78-6 Benzyl isothiocyanate 
• 2740-81-0 2-chlorophenylisothiocyanate 
• 107544-69-4 1-benzyl-3-(2-chlorophenyl)thiourea 
• 136-95-8 2-amino-benzthiazole 
• 88333-03-3 Benzyl isocyanide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 92335-48-3 methyl benzo[d]thiazole-2-sulfinate 

Downstream Products

• 137267-10-8 1-{2-[(Z)-Benzylimino]-benzothiazol-3-yl}-3-phenoxy-propan-2-ol 

Relevant articles and documents

Anti-infective and herbicidal activity of N-substituted 2-aminobenzothiazoles

In this study, a series of N-substituted 2-aminobenzothiazoles was prepared according to a recently developed method. Twelve compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia

An aerobic oxidative coupling approach for the synthesis of N-substituted 2-aminobenzothiazole derivatives using iron catalyst

A facile and convenient method was developed for the formation of novel N substituted 2-aminobenzothiazoles via an iron-catalysed condensation of 2-aminobenzothizole with different amines. This method is applicable for a wide range of aliphatic, aromatic and heterocyclic amines furnishing moderate yields of the corresponding products and thus rendering the methodology as a highly eco-friendly, inexpensive alternative to the existing methods.

Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions

2-Aminobenzothiazoles comprise a valuable structural motif, which prevails in versatile natural products and biologically active compounds. Herein, a switchable and scalable C-N coupling protocol was developed for the synthesis of these compounds from 2-chlorobenzothiazoles and primary amines. Gratifyingly, this protocol was achieved under transition-metal-free and solvent-free conditions. Moreover, introducing an appropriate amount of NaH completely switched the selectivity from mono- toward di-heteroarylation, and further investigations provided a rationale for this new finding. Furthermore, gram-scale synthesis of representative products 3a and 4a was realized by applying operationally simple and glovebox-free procedures, which revealed the practical usefulness of this work. Finally, evaluation of the quantitative green metrics provided evidence that our protocol was superior over the literature ones in terms of green chemistry and sustainability.

Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides

In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.