2406-90-8

Basic information

• Product Name: 2-Chlorobenzothiazo-6-amine
• Synonyms: 2-CHLORO-BENZOTHIAZOL-6-YLAMINE;6-Benzothiazolamine,2-chloro-(9CI);6-Benzothiazolamine, 2-chloro-;2-CHLOROBENZOTHIAZO-6-AMINE;2-Chloro-6-aminobenzothiazole;6-Amino-2-chlorobenzothiazole;2-CHLOROBENZOTHIAZO-6YL-AMINE;Benzothiazole, 6-amino-2-chloro- (6CI,7CI,8CI)
• CAS NO: 2406-90-8
• Molecular Formula: C₇H₅ClN₂S
• Molecular Weight: 184.65
• Product Categories: BENZOTHIAZOLE
• Mol File: 2406-90-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 155-157 °C
• Boiling Point: 337.292 °C at 760 mmHg
• Flash Point: 157.789 °C
• Appearance: /
• Density: 1.532
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.763
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.09±0.10(Predicted)
• CAS DataBase Reference: 2-Chlorobenzothiazo-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzothiazo-6-amine(2406-90-8)
• EPA Substance Registry System: 2-Chlorobenzothiazo-6-amine(2406-90-8)

Safety Data

• Hazardous Substances Data: 2406-90-8(Hazardous Substances Data)

Usage

General Description

2-Chlorobenzothiazole-6-amine is a chemical compound with the molecular formula C7H5ClNS. It is an organic compound that belongs to the benzothiazole class of chemicals. 2-Chlorobenzothiazo-6-amine is identified by its structure, which consists of a benzene ring fused to a six-membered thiazole ring with a chlorine atom and an amino group attached at specific positions. 2-Chlorobenzothiazole-6-amine is commonly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes. It is also utilized in the manufacturing of rubber additives and corrosion inhibitors. 2-Chlorobenzothiazo-6-amine is known to have potential toxicity and should be handled with care as it may cause skin and eye irritation upon contact.

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

Upstream product

• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 58263-00-6 6-azido-2-chloro-benzothiazole 
• 75-15-0 carbon disulfide 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 850021-27-1 2-morpholinobenzo[d]thiazol-6-amine 
• 912641-81-7 tert-butyl 2-(2-cyanobenzo[d]thiazol-6-ylamino)-2-oxoethylcarbamate 
• 1318692-71-5 6-(4-phenylbutylamino)-2-cyanobenzothiazole 
• 934270-90-3 6-(3-phenylpropylamino)-2-cyanobenzothiazole 
• 934270-89-0 6-phenethylamino-2-cyanobenzothiazole 
• 934270-88-9 6-benzylamino-2-cyanobenzothiazole 
• 1318692-88-4 6-[6-(benzyloxycarbonylamino)hexylamino]-2-cyanobenzothiazole 
• 7724-12-1 2-cyano-6-aminobenzothiazole 
• 892841-01-9 4'-fluoro-biphenyl-4-carboxylic acid (2-chloro-benzothiazol-6-yl)-amide 
• 118969-27-0 2-(6-aminobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 7714-23-0 N-(2-cyanobenzo[d]thiazol-6-yl)acetamide 

Relevant articles and documents

Site-specific immobilization of biomolecules by a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole

We report herein a new site-specific microarray immobilization method based on a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole (CBT). This immobilization strategy has been successfully applied to anchor small molecules, peptides and proteins onto microarrays.

Aminoluciferins as functional bioluminogenic substrates of firefly luciferase

Firefly luciferase is widely used as a reporter gene in assays to study gene expression, gene delivery, and so on because of its extremely high signal-to-noise ratio. The availability of a range of bioluminogenic substrates would greatly extend the applicability of the luciferin-luciferase system. Herein, we describe a design concept for functional bioluminogenic substrates based on the aminoluciferin (AL) scaffold, together with a convenient, high-yield method for synthesizing N-alkylated ALs. We confirmed the usefulness of ALs as bioluminogenic substrates by synthesizing three probes. The first was a conjugate of AL with glutamate, Glu-AL. When Glu-AL, the first membrane-impermeable bioluminogenic substrate of luciferases, was applied to cells transfected with luciferase, luminescence was not observed; that is, by using Glu-AL, we can distinguish between intracellular and extracellular events. The second was Cy5-AL, which consisted of Cy5, a near-infrared (NIR) cyanine fluorescent dye, and AL, and emitted NIR light. When Cy5-AL reacted with luciferase, luminescence derived from Cy5 was observed as a result of bioluminescence resonance energy transfer (BRET) from AL to Cy5. The NIR emission wavelength would allow a signal to be observed from deeper tissues in bioluminescence in vivo imaging. The third was biotin-DEVD-AL (DEVD=the amino acid sequence Asp-Glu-Val-Asp), which employed a caspase-3 substrate peptide as a switch to control the accessibility of the substrate to luciferase, and could detect the activity of caspase-3 in a time-dependent manner. This generalized design strategy should be applicable to other proteases. Our results indicate that the AL scaffold is appropriate for a range of functional luminophores and represents a useful alternative substrate to luciferin.

DNA-damaging activity and mutagenicity of 16 newly synthesized thiazolo[5,4-a]acridine derivatives with high photo-inducible cytotoxicity

The discovery of the potent anticancer properties of natural alkaloids in the pyrido-thiazolo-acridine series has suggested that thiazolo-acridine derivatives could be of great interest. In a continuous attempt to develop DNA-binding molecules and DNA photo-cleavers, 16 new thiazolo[5,4-a]acridines were synthesized and studied for their photo-inducible DNA-intercalative, cytotoxic and mutagenic activities, by use of the DNA methyl-green bioassay, the Alamar Blue viability assay and the Salmonella mutagenicity test using strains TA97a and TA98 with and without metabolic activation and photo-activation. Without photo-activation, one compound showed a DNA-intercalative activity in the DNA major groove while three compounds displayed intercalating properties after photo-activation. In the dark, four molecules possessed cytotoxic activities against a THP1 acute monocytic leukemia cell line while 15 derivatives displayed photo-inducible cytotoxic activity against this cell line. All compounds were mutagenic in strain TA97a with metabolic activation (+S9mix) and 15 molecules were mutagenic in strain TA98 without activation (-S9mix). Study of the quantitative structure-activity relationships (QSAR) from the Salmonella mutagenicity data revealed that several descriptors could describe cytotoxic and mutagenic activities after photo-activation. From the results of the mutagenicity test, four compounds with elevated mutagenic activities were selected for additional experiments. Their capacities to induce single-strand breaks (SSB) and chromosome-damaging effects were monitored by the comet and the micronucleus assays in normal human keratinocytes. Comparison of the minimal genotoxic concentrations showed that two compounds possessed higher capacities to induce SSB after photo-activation. In the micronucleus assay, three molecules were able to induce high numbers of micronuclei following photo-activation. Overall, the results of this study confirm that acridines are predominantly genotoxic via a DNA-intercalating mechanism in the dark, while DNA-adducts were probably induced following photo-activation.