5345-53-9

Usage

Uses

Used in Chemical Research:
1,4-Diacetamino-2-nitrobenzene is used as a research compound for studying its chemical properties and potential applications in various fields.
Used in Manufacturing Applications:
1,4-Diacetamino-2-nitrobenzene is used as an intermediate in the synthesis of other chemical products, contributing to the development of new materials and compounds.

InChI:InChI=1/C10H11N3O4/c1-6(14)11-8-3-4-9(12-7(2)15)10(5-8)13(16)17/h3-5H,1-2H3,(H,11,14)(H,12,15)

Upstream product

• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 108-24-7 acetic anhydride 
• 140-50-1 N,N'-diacetyl-1,4-phenylenediamine 
• 106-50-3 1,4-phenylenediamine 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 6086-29-9 4-acetylamino-1-amino-2-nitrobenzene 

Downstream Products

• 6086-29-9 4-acetylamino-1-amino-2-nitrobenzene 
• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 5393-46-4 4-acetamido-3-nitro-biphenyl 
• 25826-33-9 1,2,4-triaminobenzene N¹,N⁴-diacetate 
• 859952-43-5 2-nitro-1,4-bis-(4-nitro-benzoylamino)-benzene 
• 6086-30-2 N-(4-azido-3-nitro-phenyl)-acetamide 
• 859952-47-9 2,3-dinitro-1,4-bis-(4-nitro-benzoylamino)-benzene 
• 20809-93-2 4-acetylamino-2-nitro-benzenediazonium; chloride 
• 27908-96-9 benzoic acid-(4-amino-3-nitro-anilide) 

Relevant academic research and scientific papers

Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

SYNTHESIS AND TRANSFORMATION OF NITRO-N,N'-DIACETYLPHENYLENEDIAMINES

N,N'-Diacetyl-2,3-dinitro-1,4-phenylenediamine, N,N'-diacetyl-2,3-dinitro-4-nitroaminoaniline, and 1,4-bis(acetylnitroamino)-2,3-dinitrobenzene were obtained by nitration of N,N'-diacetyl-1,4-phenylenediamine by solutions of nitric acid in acetic acid or acetic anhydride.In nucleophilic substitution reactions the obtained N-nitroanilines eliminate the N-nitro group or acetyl group, depending on the nature of the nucleophile, to form the salts of the corresponding N-nitroamines.