6276-78-4

Basic information

• Product Name: BENZOTHIAZOL-2-YL-(4-CHLORO-PHENYL)-AMINE
• Synonyms: N-(4-chlorophenyl)-1,3-benzothiazol-2-amine
• CAS NO: 6276-78-4
• Molecular Formula: C₁₃H₉ClN₂S
• Molecular Weight: 260.74
• Mol File: 6276-78-4.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 401.2°C at 760 mmHg
• Flash Point: 196.4°C
• Appearance: /
• Density: 1.415g/cm³
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.747
• CAS DataBase Reference: BENZOTHIAZOL-2-YL-(4-CHLORO-PHENYL)-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOTHIAZOL-2-YL-(4-CHLORO-PHENYL)-AMINE(6276-78-4)
• EPA Substance Registry System: BENZOTHIAZOL-2-YL-(4-CHLORO-PHENYL)-AMINE(6276-78-4)

Safety Data

• Hazardous Substances Data: 6276-78-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H9ClN2S/c14-9-5-7-10(8-6-9)15-13-16-11-3-1-2-4-12(11)17-13/h1-8H,(H,15,16)

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 106-47-8 4-chloro-aniline 
• 7392-67-8 1-(4-chlorophenyl)-3-phenylthiourea 
• 615-43-0 2-iodophenylamine 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 14223-48-4 p-chlorophenyl isoselenocyanate 
• 137-07-5 2-amino-benzenethiol 
• 615-36-1 2-bromoaniline 
• 894949-65-6 C₁₃H₁₀ClIN₂S 
• 38985-64-7 o-fluorophenyl isothiocyanate 
• 65551-02-2 1-o-Fluorphenyl-3-p-chlorphenyl-2-thiocarbamid 
• 88-74-4 2-nitro-aniline 
• 1218906-35-4 N-(4-chlorophenyl)-N-(2-iodophenyl)methanediimine 
• 75-15-0 carbon disulfide 

Downstream Products

• 65416-75-3 (4-chloro-phenyl)-(3-methyl-3H-benzothiazol-2-ylidene)-amine 

Relevant articles and documents

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.

Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous mediaviatandem addition-cyclization

An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).