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Usage

Uses

Used in Chemical Synthesis:
5-Acetylamido-2-chloroaniline is used as an intermediate in the chemical synthesis of various organic compounds, particularly those involving the formation of amide and chloro groups. Its unique structure allows for the creation of a wide range of products with diverse applications.
Used in Pharmaceutical Industry:
5-Acetylamido-2-chloroaniline is used as a building block for the development of new pharmaceutical compounds. Its specific functional groups enable the design of molecules with potential therapeutic properties, making it a valuable asset in drug discovery and development.
Used in Dye Manufacturing:
5-Acetylamido-2-chloroaniline is used as a starting material in the production of various dyes and pigments. Its brown crystalline form can be further modified to create a range of colors, making it a versatile component in the dye manufacturing process.
Used in Research and Development:
5-Acetylamido-2-chloroaniline is used as a research compound for studying the properties and reactions of anilide derivatives. Its unique structure provides valuable insights into the behavior of similar compounds, contributing to the advancement of chemical knowledge and innovation.
Used in Analytical Chemistry:
5-Acetylamido-2-chloroaniline is used as a reference compound in analytical chemistry for the identification and quantification of related substances. Its distinct chemical properties make it an ideal candidate for calibration and quality control purposes in various analytical techniques.

InChI:InChI=1/C8H9ClN2O/c1-5(12)11-6-2-3-7(9)8(10)4-6/h2-4H,10H2,1H3,(H,11,12)

Upstream product

• 5540-60-3 N-(4-chloro-3-nitrophenyl)acetamide 
• 108-24-7 acetic anhydride 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 635-22-3 4-Chloro-3-nitroaniline 
• 10199-85-6 1-chloro-2,4-dinitrochlorobenzene 

Downstream Products

• 149526-85-2 N-(3-azido-4-chlorophenyl)-N'-methyl-thiourea 
• 149526-84-1 N-(3-azido-4-chlorophenyl)-thiourea 
• 155593-82-1 3-azido-4-chlorophenylisothiocyanate 
• 155593-81-0 3-azido-4-chloroaniline 
• 155593-80-9 3-azido-4-chloroacetanilide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine scaffold as DFG-out B-Raf kinase inhibitors

By combining the scaffolds of UI-125 and Sorafenib, a series of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine moiety were designed and synthesized as novel DFG-out B-RafV600E inhibitors. Among them, 20c-e, 20g and 21h displayed potent antiproliferative activities against melanoma A375 (B-RafV600E) cell lines with IC50 values of 3.190, 2.276, 1.856, 1.632 μM and 1.839 μM, respectively, comparable with the positive control Vemurafenib (IC50 Combining double low line 3.32 μM). Selected compounds were tested for the ERK inhibition in human melanoma A375 (B-RafV600E) and SK-MEL-2 (B-RafWT) cell lines by Western blot. The results revealed that our compounds inhibited the proliferation of melanoma A375 cells (B-RafV600E) through ERK pathway, without paradoxical activation of ERK in melanoma SK-MEL-2 cells (B-RafWT). Eventually, 20g and 21h were selected to confirm their inhibitory effects on tumor growth in A375 xenograft models in mice. Compound 20g exhibited equivalent antitumor efficacy in vivo (T/C Combining double low line 44.37%), compared to Sorafenib (T/C Combining double low line 37.35%), by 23-day repetitive administration of a single dose of 50 mg/kg without significant body weight loss.

Design and synthesis of tag-free photoprobes for the identification of the molecular target for CCG-1423, a novel inhibitor of the Rho/MKL1/SRF signaling pathway

CCG-1423 and related analogues represent a new class of inhibitors of Rho/MKL1/SRF-mediated gene transcription, a pathway that has been implicated in both cancer and fibrosis. The molecular target for these compounds is unknown. To facilitate its identification, a series of tag-free photoaffinity probes was designed and synthesized, each one containing a photoactivatable group and an acetylenic end group for subsequent attachment to a fluorescent tag using click chemistry. All were confirmed to maintain biological activity in a cell-based assay for inhibition of SRE-Luc expression. The functional activity of the most potent probe 24 was further confirmed in an assay for PC-3 cell migration. Photolysis of 24 in intact PC-3 cells followed by cell lysis, click ligation of a fluorescent dye, and gel electrophoresis revealed specific labeling of a single 24 kDa band that could be blocked with an active competitor. Future work will focus on identifying the labeled protein(s).

One-pot reductive conversion of nitroarenes to N-arylacetamides mediated by metallic samarium

Nitroarenes can be reduced and then converted to N-arylacetamides by metallic samarium in the presence of acetic anhydride, acetic acid and methanol in excellent yields by a one pot-procedure.

Process for the catalytic hydrogeneration of aromatic nitro compounds

PCT No. PCT/EP96/01889 Sec. 371 Date Nov. 13, 1997 Sec. 102(e) Date Nov. 13, 1997 PCT Filed May 7, 1996 PCT Pub. No. WO96/36597 PCT Pub. Date Nov. 21, 1996One object of the invention is a process for the catalytic hydrogenation of aromatic nitro compounds in solution or in melt in the presence of hydrogen and at least one noble metal catalyst, nickel catalyst or cobalt catalyst, in which process a catalytic amount of at least one vanadium compound is present, wherein the vanadium has the oxidation state 0, II, IV or V. It has been found that in the catalytic hydrogenation of aromatic nitro compounds the accumulation of hydroxylamines can be almost completely prevented by the addition of catalytic amounts of vanadium compounds, which usually results in concentrations of 1% hydroxylamine. The resulting hydrogenated products are whiter (purer) than those obtained without the addition of the vanadium compound because almost no azo or azoxy compounds are obtained. The hydrogenation, in particular the final phase, proceeds faster than without said addition. Accordingly, substantial advantages with respect to quality constancy and economy are obtained.

Synthesis of N-(3-azido-4-chlorophenyl)-N'-[3H-methyl]thiourea, an efficient photoaffinity probe for the urea carrier

Starting from commercial 4-chloro-3-nitroaniline, through a 5 step synthesis, was prepared 3-azido-4-chlorophenylisothiocyanate 5 which was reacted with [3H]-methylamine. The latter was obtained by three methods: i- [3H]-LiAlT4 reduction of benzylcarbamate gave rise to [3H][-methylamine (S.A.: >70 Ci/mmol). ii- Catalytic reduction of HCN with 3H2 lead to [3H]-CH3NH2 (S.A.: 0.7 Ci/mmol). iii- Schmidt rearrangement of [3H]-sodium acetate gave [3H]-CH3NH2 (S.A.: 29 Ci/mmol). Compound 7 at the highest specific activity had a self radiolysis rate precluding its practical use in biological studies whilst 29 Ci/mmol [3H]-7 was satisfactory.