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Cas Database

2406-90-8

2406-90-8

Identification

  • Product Name:6-Benzothiazolamine,2-chloro-

  • CAS Number: 2406-90-8

  • EINECS:

  • Molecular Weight:184.649

  • Molecular Formula: C7H5ClN2S

  • HS Code:29342000

  • Mol File:2406-90-8.mol

Synonyms:Benzothiazole,6-amino-2-chloro- (6CI,7CI,8CI);2-Chloro-6-aminobenzothiazole;6-Amino-2-chlorobenzothiazole;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:6-Amino-2-chlorobenzothiazole
  • Packaging:1g
  • Price:$ 130
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:6-Amino-2-chlorobenzothiazole
  • Packaging:1 g
  • Price:$ 122
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:6-Amino-2-chlorobenzothiazole
  • Packaging:5 g
  • Price:$ 386
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:6-Amino-2-chlorobenzothiazole
  • Packaging:10 g
  • Price:$ 616
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6-Amino-2-chlorobenzothiazole 95+%
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  • Price:$ 998
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6-Amino-2-chlorobenzothiazole 95+%
  • Packaging:1g
  • Price:$ 370
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  • Manufacture/Brand:Crysdot
  • Product Description:2-Chlorobenzo[d]thiazol-6-amine 97%
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  • Manufacture/Brand:Chemenu
  • Product Description:6-Amino-2-chlorobenzothiazole 97%
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  • Manufacture/Brand:Chemenu
  • Product Description:6-Amino-2-chlorobenzothiazole 97%
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  • Manufacture/Brand:Chemenu
  • Product Description:6-Amino-2-chlorobenzothiazole 97%
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Relevant articles and documentsAll total 11 Articles be found

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

Wang, Ping,Zhang, Chong-Jing,Chen, Ganchao,Na, Zhenkun,Yao, Shao Q.,Sun, Hongyan

, p. 8644 - 8646 (2013)

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.

Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy

Kovács, Anita K.,Hegyes, Péter,Szebeni, Gábor J.,Bogár, Krisztián,Puskás, László G.,Tóth, Gábor K.

, p. 1209 - 1215 (2019)

Abstract: The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method. Graphical Abstract: [Figure not available: see fulltext.].

Aminoluciferins as functional bioluminogenic substrates of firefly luciferase

Takakura, Hideo,Kojima, Ryosuke,Urano, Yasuteru,Terai, Takuya,Hanaoka, Kenjiro,Nagano, Tetsuo

supporting information; experimental part, p. 1800 - 1810 (2011/12/16)

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.

Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase

Reddy, Gadarla Randheer,Thompson, Walter C.,Miller, Stephen C.

supporting information; experimental part, p. 13586 - 13587 (2010/11/24)

Firefly luciferase utilizes the chemical energy of ATP and oxygen to convert its substrate, d-luciferin, into an excited-state oxyluciferin molecule. Relaxation of this molecule to the ground state is responsible for the yellow-green light emission. Synthetic cyclic alkylaminoluciferins that allow robust red-shifted light emission with the modified luciferase Ultra-Glo are described. Overall light emission is higher than that of acyclic alkylaminoluciferins, aminoluciferin, and the native substrate d-luciferin.

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

Di Giorgio, Carole,Nikoyan, Anna,Decome, Laetitia,Botta, Celine,Robin, Maxime,Reboul, Jean-Pierre,Sabatier, Anne-Sophie,Matta, Alain,De Meo, Michel

, p. 104 - 114 (2008/09/17)

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.

Process route upstream and downstream products

Process route

2-chloro-6-nitrobenzothiazole
2407-11-6

2-chloro-6-nitrobenzothiazole

2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

Conditions
Conditions Yield
2-chloro-6-nitrobenzothiazole; With iron; In ethanol; acetic acid; for 1.5h; Heating / reflux;
With sodium hydroxide; In ethanol; water; acetic acid; pH=7.5;
83%
With tin(II) chloride dihdyrate; ethanol; for 4h; Reflux;
77%
2-chloro-6-nitrobenzothiazole; With hydrogenchloride; water; tin(ll) chloride; In ethanol; at 120 ℃; Heating / reflux;
With sodium hydroxide; In ethanol; water;
61%
With hydrogenchloride; tin(ll) chloride; In ethanol; water; at 120 ℃;
61%
With hydrogenchloride; tin(II) chloride dihdyrate; In ethanol; water; for 4h; Reflux;
57.9%
With acetic acid; zinc; In tetrahydrofuran; methanol; at 60 ℃; for 2h;
56%
With iron; acetic acid; at 40 ℃; for 5h;
33%
With ethanol; iron; acetic acid;
With hydrogen; palladium on activated charcoal;
With hydrogenchloride; iron;
With iron; ammonium chloride; In water;
2-chlorobenzo[d][1,3]thiazole
615-20-3

2-chlorobenzo[d][1,3]thiazole

2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: nitric acid; sulfuric acid
2: hydrogen / Pd/C
With sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal;
Multi-step reaction with 2 steps
1: 100 percent / HNO3; H2SO4 / 3 h / 0 - 25 °C
2: 56 percent / Zn; AcOH / tetrahydrofuran; methanol / 2 h / 60 °C
With sulfuric acid; nitric acid; acetic acid; zinc; In tetrahydrofuran; methanol;
Multi-step reaction with 2 steps
1: potassium nitrate; sulfuric acid / 1.5 h / 20 °C / Cooling with ice
2: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 4 h / Reflux
With hydrogenchloride; tin(II) chloride dihdyrate; sulfuric acid; potassium nitrate; In ethanol; water;
Multi-step reaction with 2 steps
1: sulfuric acid; potassium nitrate / 0 °C
2: ammonium chloride; iron / water
With sulfuric acid; iron; ammonium chloride; potassium nitrate; In water;
6-azido-2-chloro-benzothiazole
58263-00-6

6-azido-2-chloro-benzothiazole

2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

Conditions
Conditions Yield
With potassium methanolate; In 1,4-dioxane; methanol; Product distribution; Irradiation;
33%
carbon disulfide
75-15-0,12122-00-8

carbon disulfide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

Conditions
Conditions Yield
Multistep reaction; (i) KSCN, Br2, (ii) aq. NaOH, (iii) /BRN= 1098293/, (iv) SO2Cl2;
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

2-chlorobenzo[d]thiazol-5-amine
80945-82-0

2-chlorobenzo[d]thiazol-5-amine

Conditions
Conditions Yield
With hydrogen; In ethanol;
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

Conditions
Conditions Yield
aus der Nitro-Verb.;
Entspr. Nitroverb., Raney-Ni/H2;
6-Nitro-2-chlor-benzothiazol, Fe-Pulver, Essigsaeure;
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

2-(6-aminobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
118969-27-0

2-(6-aminobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: dimethylsulfoxide
2: (i) NaNH2, liq. NH3, (ii) /BRN= 1567902/, MeOH
In dimethyl sulfoxide;
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid
138962-06-8

N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid

Conditions
Conditions Yield
With zinc/copper couple; potassium carbonate; In butanone; at 80 ℃; for 3h; ultrasonic irradiation;
86%
With copper; potassium carbonate; potassium iodide; In butanone; for 2h; Irradiation;
76%
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

4′-fluoro-[1,1′-biphenyl]-4-carbonyl chloride
782480-50-6

4′-fluoro-[1,1′-biphenyl]-4-carbonyl chloride

4'-fluoro-biphenyl-4-carboxylic acid (2-chloro-benzothiazol-6-yl)-amide
892841-01-9

4'-fluoro-biphenyl-4-carboxylic acid (2-chloro-benzothiazol-6-yl)-amide

Conditions
Conditions Yield
With pyridine; In dichloromethane; at 20 ℃;
2-chlorobenzothiazol-6-ylamine
2406-90-8

2-chlorobenzothiazol-6-ylamine

C<sub>10</sub>H<sub>11</sub>ClO<sub>3</sub>

C10H11ClO3

N-(2-chlorobenzo[d]thiazol-6-yl)-2,4-dimethoxy-3-methylbenzamide

N-(2-chlorobenzo[d]thiazol-6-yl)-2,4-dimethoxy-3-methylbenzamide

Conditions
Conditions Yield
With potassium carbonate; In dichloromethane; at 20 ℃;
70%

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