5443-33-4

Usage

Uses

Used in Dye and Pigment Production:
5-CHLORO-2-NITROACETYLANILINE is used as an intermediate in the production of dyes and pigments for various applications. Its unique chemical structure contributes to the color properties of the final products, making it a valuable component in the manufacturing process.
Used in Chemical Research:
5-CHLORO-2-NITROACETYLANILINE serves as a research compound in the field of organic chemistry. It is utilized in the synthesis of various organic compounds and can be used to study the reactivity and properties of different functional groups.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5-CHLORO-2-NITROACETYLANILINE may also have potential applications in the pharmaceutical industry. Its unique chemical structure could be used in the development of new drugs or as a building block for the synthesis of pharmaceutical compounds.

InChI:InChI=1/C8H7ClN2O3/c1-5(12)10-7-4-6(9)2-3-8(7)11(13)14/h2-4H,1H3,(H,10,12)

Upstream product

• 588-07-8 3-Chloroacetanilide 
• 1635-61-6 5-chloro-2-nitroaniline 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 63471-10-3 acetic acid-(2-nitro-5-phenoxy-anilide) 
• 1635-61-6 5-chloro-2-nitroaniline 
• 87049-66-9 2'-amino-5'-chloroacetanilide 
• 857786-53-9 bis-(3-acetylamino-4-nitro-phenyl)-disulfide 
• 6942-98-9 5-chloro-8-nitroquinoline 
• 102653-54-3 5-chloro-2-methyl-8-nitroquinoline 
• 128765-25-3 5-(3-oxo-1,4-benzothiazin-7-yloxy)-2-nitroacetanilide 
• 128765-26-4 N-[5-(4-Methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-7-yloxy)-2-nitro-phenyl]-acetamide 
• 128765-27-5 N-[5-(4-Ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-7-yloxy)-2-nitro-phenyl]-acetamide 
• 128765-28-6 N-[5-(4-Benzyl-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-7-yloxy)-2-nitro-phenyl]-acetamide 
• 128765-29-7 N-{5-[4-(4-Chloro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-7-yloxy]-2-nitro-phenyl}-acetamide 
• 102790-48-7 3,3'-diamino-4,4'-dinitrodiphenyl sulfide 
• 65671-10-5 1-(3-carbomethoxythioureido)-2-nitro-5-propylthiobenzene 
• 57780-75-3 2-nitro-5-n-propylthioaniline 

Relevant academic research and scientific papers

Design, synthesis, kinetic, molecular dynamics, and hypoglycemic effect characterization of new and potential selective benzimidazole derivatives as Protein Tyrosine Phosphatase 1B inhibitors

Protein-tyrosine phosphatase 1B (PTP1B) is a negative regulator of insulin signaling pathway and has been validated as a therapeutic target for type 2 diabetes. A wide variety of scaffolds have been included in the structure of PTP1B inhibitors, one of them is the benzimidazole nucleus. Here, we report the design and synthesis of a new series of di- and tri- substituted benzimidazole derivatives including their kinetic and structural characterization as PTP1B inhibitors and hypoglycemic activity. Results show that compounds 43, 44, 45, and 46 are complete mixed type inhibitors with a Ki of 12.6 μM for the most potent (46). SAR type analysis indicates that a chloro substituent at position 6(5), a β-naphthyloxy at position 5(6), and a p-benzoic acid attached to the linker 2-thioacetamido at position 2 of the benzimidazole nucleus, was the best combination for PTP1B inhibition and hypoglycemic activity. In addition, molecular dynamics studies suggest that these compounds could be potential selective inhibitors from other PTPs such as its closest homologous TCPTP, SHP-1, SHP-2 and CDC25B. Therefore, the compounds reported here are good hits that provide structural, kinetic, and biological information that can be used to develop novel and selective PTP1B inhibitors based on benzimidazole scaffold.

Transition-metal-free mono- or dinitration of protected anilines

An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.

BENZIMIDAZOLECARBOXAMIDES AS INHIBITORS OF FAK

This invention relates to benzimadolecarboxamides of formula (I) which are inhibitors of focal adhesion kinase, and as such are useful for treating proliferative diseases

Synthesis and in vitro cysticidal activity of new benzimidazole derivatives

Despite albendazole being the drug of choice in neurocysticercosis treatment, its low solubility limits its bioavailability; therefore, more research is required in order to find new molecules with cestocidal activity and adequate aqueous solubility. A set of 13 benzimidazole derivatives were synthesized and their in vitro activities were evaluated against Taenia crassiceps cysts, using albendazole sulfoxide as reference molecule, showing that two of them exhibited good activity. Molecular modelling revealed that the cysticidal efficacy depends on the presence on the molecule of an H in the 1-position, a planar carbamate group at 2-position, and if the substituent in 5-position is voluminous, it should be orthogonal to the benzimidazole ring.

Preparation of N-methoxycarbonyl-N'-[2-nitro-4(5)-propyl-thiophenyl]thiourea as prodrugs of albendazole

N-methoxycarbonyl-N'-(2-nitro-4-propylthiophenyl)thiourea and N-methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)thiourea, prodrugs of albendazole, have been synthesized. The biotransformation in rats, after oral administration of these prodrugs to albendazole and albendazole sulphoxide, is described.

Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications

In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.

Ortho-Selective Nitration of Acetanilides with Nitrogen Dioxide in the Presence of Ozone

In the presence of ozone, nitrogen dioxide rapidly reacts with acetanilides ortho-selectively at low temperatures, giving a high proportion of ortho-nitro derivatives in good yields.

Diuretic and antihypertensive benzimidazoles

The invention relates to compounds which exhibit diuretic and antihypertensive properties and have the following structures: STR1 or pharmaceutically acceptable salts thereof, wherein: X=halogen or trifluoromethyl Y1 and Y2 =independently hydrogen, alkyl, acyl, aryl, substituted aryl or heterocycle, R1 =hydrogen, lower alkyl, aryl, substituted aryl, benzyl, substituted benzyl, aralkyl, heterocycle or substituted heterocycle, n=O or an integer from 1-4 R2 =amino, substituted amino, guanidino, substituted guanidino, halogen, alkyl, substituted alkyl, aryl, substituted aryl or heterocycle, and R3 =hydrogen, lower alkyl, aryl, substituted aryl, benzyl, substituted benzyl, aralkyl, heterocycle, substituted heterocycle or acyl.