2942-06-5

Basic information

• Product Name: 6-Nitrobenzothiazole
• Synonyms: 6-Nitro-1,3-benzothiazole;Benzothiazole, 6-nitro-;6-NITROBENZOTHIAZOLE;Benzothiazole, 6-nitro- (6CI,7CI,8CI,9CI);6-NITROBENZOTHIAZOLE 98+%;6-nitrobenzo[d]thiazole;6-Nitrobenzothiazole 99%
• CAS NO: 2942-06-5
• Molecular Formula: C₇H₄N₂O₂S
• Molecular Weight: 180.18
• EINECS: 220-933-9
• Product Categories: BENZOTHIAZOLE;Building Blocks;Heterocyclic Building Blocks;Thiazoles;Aromatics;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 2942-06-5.mol

Chemical Properties

• Melting Point: 175-178 °C(lit.)
• Boiling Point: 333.7 °C at 760 mmHg
• Flash Point: 155.6 °C
• Appearance: /
• Density: 1.525 g/cm³
• Vapor Pressure: 0.000261mmHg at 25°C
• Refractive Index: 1.729
• Storage Temp.: Refrigerator
• PKA: -1.33±0.10(Predicted)
• BRN: 7824
• CAS DataBase Reference: 6-Nitrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Nitrobenzothiazole(2942-06-5)
• EPA Substance Registry System: 6-Nitrobenzothiazole(2942-06-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2942-06-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Nitrobenzothiazole is used as a chemical intermediate for the preparation of 4-amino-3-sulfanylbenzonitrile and 2-amino-5-nitrobenzothiole, which are achieved through alkaline hydrolysis. These compounds have potential applications in the development of pharmaceuticals and other chemical products.
Used in Research and Development:
The XCORFE (Xnucleus-proton correlation with fixed evolution time) pulse sequence of 6-nitrobenzothiazole has been tested, indicating its use in research and development for understanding its chemical properties and potential applications in various industries.
Used in Pharmaceutical Industry:
As a related compound of 1,2,3-benzothiadiazoles, 6-Nitrobenzothiazole may have potential applications in the pharmaceutical industry, possibly as a building block for the synthesis of new drugs or drug candidates. Its chemical properties and reactivity make it a valuable compound for further exploration and development in this field.

InChI:InChI=1/C7H4N2O2S/c10-9(11)5-1-2-6-7(3-5)12-4-8-6/h1-4H

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 64-18-6 formic acid 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 131123-99-4 6-nitrobenzo[d]thiazole-2-carboxylic acid 
• 1131-76-6 2-iodo-6-nitro-1,3-benzothiazole 
• 108-98-5 thiophenol 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 1123-99-5 2-iodobenzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 124-38-9 carbon dioxide 
• 68-12-2 N,N-dimethyl-formamide 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 533-30-2 1,3-benzothiazol-6-amine 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 67219-66-3 6-amino-7-n-butylbenzothiazole 
• 67219-67-4 7-phenethyl-benzothiazol-6-ylamine 
• 65225-74-3 5-(2-amino-5-nitro-phenylsulfanyl)-4-chloro-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one 
• 94834-02-3 1-(6-nitrobenzo[d]thiazol-2-yl)ethanone 
• 18463-85-9 6-dimethylaminophenylazobenzthiazole 
• 59484-53-6 7-benzyl-6-nitroso-benzothiazole 
• 75804-80-7 6-Chloro-7-methyl-benzothiazole 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 501-58-6 (E)-1,2-bis(4-methoxyphenyl)diazene 
• 75804-81-8 7-Benzyl-6-chloro-benzothiazole 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 72206-92-9 7-methyl-6-nitrobenzothiazole 

Relevant articles and documents

Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption

Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.

Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer's disease

In this study, four series of compounds with benzoxazolone and benzothiazolone cores were designed, synthesized and evaluated as multifunctional agents against Alzheimer's disease (AD). Additionally, in order to shed light on the effect of the carbonyl groups of benzoxazolone/benzothiazolone, benzoxazole/benzothiazole-containing analogues were also synthesized and evaluated. Inhibition potency of all final compounds towards cholinesterase enzymes and their antioxidant activity were tested. Subsequently, the anti-inflammatory activity, cytotoxicity, apoptosis, and Aβ aggregation inhibition tests were also performed for selected compounds. The results indicated that compounds 11c, a pentanamide derivative with benzothiazolone core, and 14b, a keton derivative with benzothiazolone core, were considered as promising multi-functional agents for further investigation against AD. The reversibility, kinetic and molecular docking studies were also performed for the compounds with the highest AChE 14b (eeAChE IC50 = 0.34 μM, huAChE IC50 = 0.46 μM) and BChE 11c (eqBChE IC50 = 2.98 μM, huBChE IC50 = 2.56 μM) inhibitory activities.

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthetic method of ammonium acetate-mediated benzothiazole compound

The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

A Double-Clicking Bis-Azide Fluorogenic Dye for Bioorthogonal Self-Labeling Peptide Tags

Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. This proof-of-principle study reports on the synthesis and fluorogenic characterization of a new, double-quenched, bis-azide fluorogenic probe suitable for bioorthogonal two-point tagging of small peptide tags by double strain-promoted azide-alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis-cyclooctynylated peptide sequences, which could also serve as possible self-labeling small peptide tag motifs. The first example of a fluorogenic molecular probe has been developed that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. The new, double-quenched, bis-azide fluorogenic probe can bind to small bis-cyclooctynylated peptide tags through a double strain-promoted click reaction (see figure; SPAAC=strain-promoted alkyne-azide cycloaddition). The probe exhibits remarkable increase in fluorescence intensity with peptide sequences that can serve as possible self-labeling small peptide tags.

Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst

B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.

Ionic Liquid-Catalyzed C-S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

The construction of the C-S bond using CO2 as a C1 feedstock can be considered as a green route for the synthesis of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO2 and hydrosilane under mild conditions (e.g., 60 °C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO2 as a C1 building block under metal-free and mild conditions.

Enhanced treatment regimens using mTor inhibitors

The present invention provides for methods and pharmaceutical compositions comprising inhibitors of mTorC1 and/or mTorC2. In some aspects, the invention provides for treatment regimens resulting in enhanced treatment efficacy and better tolerability.

COMBINATION OF KINASE INHIBITORS AND USES THEREOF

The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.