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

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

Downstream Products

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

Relevant articles and documents

Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by: Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

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.

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).