16588-06-0

Basic information

• Product Name: 4-CHLORO-3-NITROBENZAMIDE
• Synonyms: 4-chlor-3-nitrobenzamid;BUTTPARK 121\15-25;4-CHLORO-3-NITROBENZAMIDE;3-NITRO-4-CHLOROBENZAMIDE
• CAS NO: 16588-06-0
• Molecular Formula: C₇H₅ClN₂O₃
• Molecular Weight: 200.58
• EINECS: 240-644-1
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 16588-06-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 148-150°C
• Boiling Point: 315.6 °C at 760 mmHg
• Flash Point: 144.7 °C
• Appearance: /
• Density: 1.52 g/cm³
• Vapor Pressure: 0.000432mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 645210
• CAS DataBase Reference: 4-CHLORO-3-NITROBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-3-NITROBENZAMIDE(16588-06-0)
• EPA Substance Registry System: 4-CHLORO-3-NITROBENZAMIDE(16588-06-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36-37
• RTECS: CV2465000
• TSCA: Yes
• Hazardous Substances Data: 16588-06-0(Hazardous Substances Data)

Usage

Description

4-CHLORO-3-NITROBENZAMIDE is a chemical compound characterized by the molecular formula C7H5ClN2O3. It features a benzene ring with a chlorine atom at the 4-position and a nitro group at the 3-position, which is connected to an amide group. 4-CHLORO-3-NITROBENZAMIDE is recognized for its high reactivity and is utilized in various applications due to its unique structural properties.

Uses

Used in Organic Synthesis:
4-CHLORO-3-NITROBENZAMIDE is used as a building block in organic synthesis for the creation of various pharmaceuticals and agrochemicals. Its unique structure allows it to be a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-CHLORO-3-NITROBENZAMIDE is employed as a reagent in chemical reactions. Its potential applications in this field are being explored due to its reactivity and the possibility of it serving as a precursor for the synthesis of new medicinal compounds.
Used in Chemical Reactions:
4-CHLORO-3-NITROBENZAMIDE is utilized as a reagent in chemical reactions, where its high reactivity is leveraged to facilitate specific transformations or to produce desired products in the synthesis process.
Used in the Production of Pharmaceuticals and Agrochemicals:
As a key component in the manufacturing process, 4-CHLORO-3-NITROBENZAMIDE is used in the production of various pharmaceuticals and agrochemicals, contributing to the development of new and effective products in these industries.

InChI:InChI=1/C7H5ClN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)

Upstream product

• 96-99-1 4-chloro-3-nitrobenzoate 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 7664-41-7 ammonia 
• 38818-50-7 4-chloro-3-nitro-benzoyl chloride 
• 74-11-3 para-chlorobenzoic acid 
• 7697-37-2 nitric acid 
• 619-56-7 4-chlorobenzamide 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 506-68-3 bromocyane 
• 63603-09-8 methyl 4-chloro-3-methoxy-5-nitrobenzoate 
• 91367-05-4 methyl 4-chloro-3-methylbenzoate 
• 2137975-62-1 4-chloro-3-methoxy-5-nitrobenzamide 
• 1336-21-6 ammonium hydroxide 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 857488-34-7 4-methylsulfanyl-3-nitro-benzoic acid amide 
• 860683-98-3 4-ethylsulfanyl-3-nitro-benzoic acid amide 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 3544-24-9 3-Aminobenzamide 
• 19694-10-1 4-chloro-3-amino-benzoic acid amide 
• 1224590-61-7 C₁₅H₁₂N₂O₆ 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Amidobenzimidazole Derivatives as Stimulator of Interferon Genes (STING) Receptor Agonists

Stimulator of interferon genes (STING) is an endoplasmic reticulum-localized adaptor protein (STING receptor) that has been shown to be activated by binding to natural cyclic dinucleotide (CDN) ligands and plays a vital role in innate immune sensing of exogenous or endogenous DNA, which then induces type I interferons and other cytokines. In this paper, we described a series of amidobenzimidazole STING agonists with high potency for the STING receptor and presented the relevant structure-activity relationships (SARs). The relative potencies of compounds 16g, 24b, and 24e were measured by a STING competition binding assay. A more thorough study of the effect on the STING signaling pathway demonstrated that three compounds, 16g, 24b, and 24e, significantly increased the protein levels and mRNA levels of IFN-β, CXCL10, and IL-6, and 24b as a representative compound effectively triggered the phosphorylation of STING, TBK1, and IRF3 in both human peripheral blood mononuclear cells (hPBMCs) and WT THP-1 cells. In addition, compound 24b demonstrated impressive antitumor efficacy in mice with established syngeneic colon tumors by intravenous administration. Furthermore, the pharmacokinetic profile of compound 24b was fully evaluated.

STING HETEROCYCLE AGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of STING, and the treatment of STING-mediated disorders.

Synthesis and evaluation of sulfonylnitrophenylthiazoles (SNPTs) as thyroid hormone receptor-coactivator interaction inhibitors

We previously identified a series of methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its coactivators. MSNBs inhibit coactivator binding through irreversible modification of cysteine 298 of the thyroid hormone receptor (TR). Although MSNBs have better pharmacological features than our first generation inhibitors (β-aminoketones), they contain a potentially unstable ester linkage. Here we report the bioisosteric replacement of the ester linkage with a thiazole moiety, yielding sulfonylnitrophenylthiazoles (SNPTs). An array of SNPTs representing optimal side chains from the MSNB series was constructed using parallel chemistry and evaluated to test their antagonism of the TR-coactivator interaction. Selected active compounds were evaluated in secondary confirmatory assays including regulation of thyroid response element driven transcription in reporter constructs and native genes. In addition the selected SNPTs were shown to be selective for TR relative to other nuclear hormone receptors (NRs).