28620-12-4

Basic information

• Product Name: 6-Nitro-2-benzothiazolinone
• Synonyms: 6-NITRO-2-BENZOTHIAZOLINONE;6-NITRO-BENZOTHIAZOL-2-ONE;6-nitro-2(3H)-benzothiazolone;2(3H)-Benzothiazolone,6-nitro-(9CI);6-Nitro-2,3-dihydro-1,3-benzothiazol-2-one;6-nitro-2H-benzothiazolinone;6-Nitrobenzo[d]thiazol-2(3H)-one;2(3H)-Benzothiazolone,6-nitro
• CAS NO: 28620-12-4
• Molecular Formula: C₇H₄N₂O₃S
• Molecular Weight: 196.18
• Product Categories: BENZOTHIAZOLE;Building Blocks;Heterocyclic Building Blocks;Thiazolines/Thiazolidines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 28620-12-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 246 °C (dec.)(lit.)
• Boiling Point: 468.1 °C at 760 mmHg
• Flash Point: 236.9 °C
• Appearance: /
• Density: 1.603 g/cm³
• Vapor Pressure: 2.19E-09mmHg at 25°C
• Refractive Index: 1.701
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.78±0.20(Predicted)
• CAS DataBase Reference: 6-Nitro-2-benzothiazolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Nitro-2-benzothiazolinone(28620-12-4)
• EPA Substance Registry System: 6-Nitro-2-benzothiazolinone(28620-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 28620-12-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Nitro-2-benzothiazolinone is used as a starting reagent for the synthesis of 3-alkyl-6-nitro-2-benzothiazolinones. These synthesized compounds can have various applications in different industries, such as pharmaceuticals, agrochemicals, or materials science, due to their potential biological activities or properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Nitro-2-benzothiazolinone is used as an intermediate in the synthesis of various drug molecules. Its unique structure allows for the development of new compounds with potential therapeutic effects, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
6-Nitro-2-benzothiazolinone may also be utilized in the agrochemical industry as a precursor for the development of new pesticides or other agrochemical products. Its chemical properties can be exploited to create compounds with specific activities against pests or diseases, enhancing crop protection and yield.
Used in Materials Science:
In the field of materials science, 6-Nitro-2-benzothiazolinone could be used as a component in the development of novel materials with specific properties, such as improved stability, reactivity, or optical characteristics. Its integration into material systems can lead to innovative applications in various industries.
Overall, 6-Nitro-2-benzothiazolinone is a versatile chemical compound with potential applications across multiple industries, primarily due to its use as a starting reagent in the synthesis of other compounds with specific properties and functions.

InChI:InChI=1/C7H4N2O3S/c10-7-8-5-2-1-4(9(11)12)3-6(5)13-7/h1-3H,(H,8,10)

Upstream product

• 934-34-9 2(3H)-Benzothiazolone 
• 625-58-1 ethyl nitrate 
• 4845-58-3 6-nitrobenzo[d]thiazole-2(3H)-thione 
• 1131-75-5 2-fluoro-6-nitro-benzothiazole 
• 63321-86-8 2-methoxybenzothiazole 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 941-57-1 benzothiazole-2-sulphonic acid 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 934-34-9 2-hydroxybenzothiazole 
• 3621-99-6 2-methylthio-6-nitrobenzothiazole 
• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 21554-41-6 2-(methylsulfonyl)-6-nitrobenzo[d]thiazole 

Downstream Products

• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 121999-16-4 ω-(6-nitro-2-benzothiazolon-3-yl)acetophenone 
• 533-30-2 1,3-benzothiazol-6-amine 
• 34976-39-1 Tioxacin 
• 56354-98-4 6-Amino-1,3-benzothiazol-2(3H)-one 

Relevant articles and documents

Benzo[d]thiazol-2(3H)-ones as new potent selective CB2 agonists with anti-inflammatory properties

The high distribution of CB2 receptors in immune cells suggests their important role in the control of inflammation. Growing evidence offers this receptor as an attractive therapeutic target: selective CB2 agonists are able to modula

Identification and characterization of benzo[d]oxazol-2(3H)-one derivatives as the first potent and selective small-molecule inhibitors of chromodomain protein CDYL

Chemical probes of epigenetic ‘readers’ of histone post-translational modifications (PTMs) have become powerful tools for mechanistic and functional studies of their target proteins in physiology and pathology. However, only limited ‘reader’ probes have been developed, which restricted our understanding towards these macromolecules and their roles in cells or animals. Here, we reported a structure-guided approach to develop and characterize benzo [d]oxazol-2(3H)-one analogs as the first potent and selective small-molecule inhibitors of chromodomain Y-like (CDYL), a histone methyllysine reader protein. The binding conformation between the chromodomain of CDYL and the modified peptidomimetics was studied via molecular docking and dynamic simulations, facilitating subsequent virtual screening of tens of hits from Specs chemical library validated by SPR technique (KD values: from 271.1 μM to 5.4 μM). Further design and synthesis of 43 compounds helped to interpret the structure-activity relationship (SAR) that lead to the discovery of novel small-molecule inhibitors of CDYL. Compound D03 (KD: 0.5 μM) was discovered and showed excellent selectivity among other chromodomain proteins, including CDYL2 (>140 folds), CDY1 (no observed binding) and CBX7 (>32 folds). Moreover, we demonstrated that D03 engaged with endogenous CDYL in a dose-dependent manner, and perturbed the recruitment of CDYL onto chromatin, resulting in transcriptional derepression of its target genes. Finally, the results showed that D03 promoted the development and branching of neurodendrites by inhibiting CDYL in hippocampal and cortical cultured neurons. This study not only discovers the first selective small-molecule inhibitors of CDYL, but provids a new chemical tool to intervene the dynamic nature of bio-macromolecules involved in epigenetic mechanism.

AZABENZIMIDAZOLES AND THEIR USE AS AMPA RECEPTOR MODULATORS

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, [formula (I) should be inserted here]. Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods

6-Sulfonylbenzothiazolones as potential scaffolds for the design of 5-HT6 ligands

5-HT6 Receptors are relatively recently discovered receptors that interact with cholinergic, glutamatergic, GABAergic and dopaminergic transmission systems. These receptors have been implicated in the CNS system as therapeutic targets in applications such as psychosis, reduction of body weight or Alzheimer's disease. As part of our efforts to develop 5-HT6 antagonists, we explored the benzothiazolone scaffold substituted in position 3 or 6 respectively with ethylamino chains and an aromatic ring connected through a sulfonyl linker. Final compounds were evaluated in radioligand binding assays for their ability to interact with 5-HT6 receptors. Their potential cytotoxic effects were determined on the human neuroblastoma cell line SY5Y. They showed very low cytotoxicity, and one of them has submicromolar affinity for 5-HT6 receptors.

Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives

A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]

Novel heterocyclic derivatives, preparation method and pharmaceutical compositions containing same

Compounds of formula (I): wherein: X represents an oxygen atom or a sulphur atom or a group CH2 or R1 and R2 represent a hydrogen atom, or a group as defined in the description, A represents an alkylene chain as described

Synthesis of semicarbazones and thiosemicarbazones of 1-(2-benzothiazolon-3-yl) propanones

Semi- and thiosemicarbazones were synthesized by the reaction of 1-(2-benzothiazolon-3-yl)propanones with semi- and thiosemicarbazide. These compounds are more active in stimulating plant growth than the starting propanones.

Synthesis of 2-Oxo and 2-Thioxo-3(2H)-benzothiazoleethanimic Acid Anhydride with Acetic Acid and Related Products

The reaction of the appropriate 2-benzothiazolinone with 2-chloroacetamide under basic conditions afforded the 2-oxo-3(2H)-benzothiazolineacetamides 6-9.The 2-thioxo-3(2H)-benzothiazolineacetamide (10) was prepared by the reaction of 3-(carbethoxymethyl)benzothiazoline-2-thione with ammonium hydroxide.The reaction of acetamides 6-10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11-18 in excellent yields.The omission of the catalyst in the same reaction furnished a mixture containing 57percent of the titled compound, 37percent of the nitrile and 6percent of an unknown.Possible mechanism and supporting nmr, ir and mass spectral data are discussed.

Synthesis and Reactions of Azido-benzothiazoles and -benzothiophens; Novel Thiazolobenzoxazoles and Dihydrothienobenzoxazoles

6-Azidobenzothiazole and its 2-methyl and 2-methylthio-derivatives were prepared from the corresponding amine and gave the thiazolobenzoxazoles (8)-(10), on thermolysis in a polyphosphoric-acetic acid mixture. 6,7-Dihydro-2-methylthienobenzoxazole 8,8-dioxide (12) was prepared similarly.An improved method of synthesis of 2-fluoro-6-nitrobenzothiazole is reported.