16264-05-4

Basic information

• Product Name: 1,4-bis(4-nitrophenyl)piperazine
• Synonyms: 1,4-bis(4-nitrophenyl)piperazine;Einecs 240-371-8
• CAS NO: 16264-05-4
• Molecular Formula: C₁₆H₁₆N₄O₄
• Molecular Weight: 328.32264
• EINECS: 240-371-8
• Mol File: 16264-05-4.mol

Chemical Properties

• Melting Point: 258.5-259 °C
• Boiling Point: 556.8°Cat760mmHg
• Flash Point: 290.5°C
• Appearance: /
• Density: 1.364g/cm³
• Vapor Pressure: 1.96E-12mmHg at 25°C
• Refractive Index: 1.648
• PKA: 1.36±0.40(Predicted)
• CAS DataBase Reference: 1,4-bis(4-nitrophenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(4-nitrophenyl)piperazine(16264-05-4)
• EPA Substance Registry System: 1,4-bis(4-nitrophenyl)piperazine(16264-05-4)

Safety Data

• Hazardous Substances Data: 16264-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-bis(4-nitrophenyl)piperazine is used as a chemical intermediate for the synthesis of pharmaceutical drugs, leveraging its structural properties to create novel therapeutic agents.
Used in Organic Synthesis:
1,4-bis(4-nitrophenyl)piperazine is used as a building block in organic synthesis for creating a variety of complex organic compounds, contributing to the development of new materials and chemical entities.
Used in Cancer Research:
1,4-bis(4-nitrophenyl)piperazine is used as a potential anti-cancer agent in research settings, where its effects on cancer cells and mechanisms of action are studied to explore its therapeutic potential.
Used in Enzyme Inhibition Studies:
1,4-bis(4-nitrophenyl)piperazine is used as an enzyme inhibitor in biological research, helping to understand its interaction with specific enzymes and its potential use in treating enzyme-related diseases.
Used in Dye and Pigment Production:
1,4-bis(4-nitrophenyl)piperazine is used in the production of dyes and pigments, capitalizing on its chemical properties to create colorants for various applications.

InChI:InChI=1/C16H16N4O4/c21-19(22)15-5-1-13(2-6-15)17-9-11-18(12-10-17)14-3-7-16(8-4-14)20(23)24/h1-8H,9-12H2

Upstream product

• 110-85-0 piperazine 
• 100-00-5 4-chlorobenzonitrile 
• 6269-89-2 1-(4-Nitrophenyl)piperazine 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 692259-80-6 1,4-bis[4-(N²,N³-bis(tert-butoxycarbonyl)guanidino)phenyl]piperazine 
• 692259-85-1 di-tert-butul 2-(4-[4-(4-[1,3-bis(tert-butoxycarbonyl)tetrahydro-1H-2-imidazolyliden]aminophenyl)piperazino]phenylimino)-1,3-imidazolidinedicarboxylate 
• 7479-12-1 4-(4-(4-aminophenyl)piperazin-1-yl)benzenamine 
• 184177-83-1 2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one 
• 7061-88-3 1,4-Bis-<2,4,6-trinitro-phenyl>-piperazin 

Relevant articles and documents

Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions

A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.

Preparation method of posaconazole intermediate

The invention discloses a preparation method of a posaconazole intermediate shown as a formula I. According to the method, p-brominated nitrobenzene and anhydrous piperazine are used as raw materials, and a target product is prepared through a condensation reaction, a reduction reaction, a monoacylation reaction, a cyclization reaction and a diazotization hydrolysis reaction. Compared with a synthesis method taking 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine as a starting material in the prior art, the preparation method provided by the invention has the advantages that the raw materials are easy to obtain, the reaction efficiency is high, the reaction conditions are mild, the yield of a target product is high, the operation is simple and convenient, the efficiency is high, and the cost is low.

1,4-Diarylpiperazines and analogs as anti-tubercular agents: Synthesis and biological evaluation

Despite progress in modern chemotherapy to combat tuberculosis, the causative pathogen Mycobacterium tuberculosis (M.tb.) is far from eradicated. Bacillary resistance to anti-mycobacterial agents, bacillary persistence and human immunodeficiency virus (HIV) co-infection hamper current drug treatment to completely cure the infection, generating a constant demand for novel drug candidates to tackle these problems. A small library of novel heterocyclic compounds was screened in a rapid luminometric in vitro assay against the laboratory M.tb. strain H37Rv. A group of amidines was found to have the highest potency and was further evaluated for acute toxicity against C3A hepatocytes. Next, the most promising compounds were evaluated for activity against a multi-drug resistant clinical isolate. The group of amidines was also tested for their ability to kill intracellular M.tb. residing in mouse J774A.1 macrophages. Finally, we report on a correlation between the structural differences of the compounds and their anti-mycobacterial activity.

Bisguanidine, Bis(2-aminoimidazoline), and Polyamine Derivatives as Potent and Selective Chemotherapeutic Agents against Trypanosoma brucei rhodesiense. Synthesis and in Vitro Evaluation

The in vitro screening for trypanocidal activity against Trypanosoma brucei rhodesiense of an in-house library of 62 compounds [i.e. alkane, diphenyl, and azaalkane bisguanidines and bis-(2-aminoimidazolines)], which were chosen for their structural similarity to the trypanocidal agents synthalin (1,10-decanediguanidine) and 4,4′-diguanidinodiphenylmethane and the polyamine N1-(3-amino-propyl)propane-1,3-diamine, respectively, is reported. The original synthetic procedure for the preparation of 21 of these compounds is also reported. Most compounds displayed low micromolar antitrypanosomal activity, with five of them presenting a nanomolar inhibitory action on the parasite: 1,9-nonanediguanidine (1c), 1,12-dodecanediguanidine (1d), 4,4′ -bis[1,3-bis(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine (28a), 4,4′-bis(4,5-dihydro-1H-2-imidazolylamino)diphenylamine (28b), and 4,4′-diguanidino-diphenylamine (32b). Those molecules that showed an excellent in vitro activity as well as high selectivity for the parasite [e.g. 1c (IC50 = 49 nM; SI > 5294), 28b (IC50 = 69 nM; SI = 3072), 32b (IC50 = 22 nM; SI = 29.5), 41b (IC50 = 118 nM; SI = 881)] represent new antitrypanosomal lead compounds.

Synthesis, antituberculosis activity, and DNA binding affinity of a highly diverse library of 1,4-diarylpiperazines

A library of eighteen 1,4-diarylpiperazines has been synthesized and evaluated for antituberculosis activity and DNA binding affinity. Among them, 4,4′-(1,4-piperazinediyl)bis(N-alkylbenzenecarboximidamides) emerged as attractive leads for further drug development.

Chemotherapeutically active nitro compounds. I. Nitroanilines

More than 200 nitro compounds, most of them nitroaniline derivatives substituted with one or more radicals having a basic reaction, were prepared and investigated as to their therapeutic activity against bacteria, fungi, protozoa, helminths, viruses and tumors. Several mono nitrobenzenes with a radical having a basic reaction showed a weak in vitro activity against gram positive bacteria and against Crocker's sarcoma 180; they also showed systemic activity against nematodes (Aspiculuris tetraptera) and viruses. The majority of therapeutically active compounds with pronounced in vitro activity against Trichomonas fetus, Entamoeba histolytica, Schistosoma mansoni, cestodes, nematodes (Ancylostoma caninum), viruses (influenza, MHV, SAV and EMC) and various types of carcinoma (Ehrlich's carcinoma, leukemia 1210, Crocker's sarcoma 180) were dinitrobenzene derivatives with one radical having a basic reaction and electropositive groups or unreactive or reactive chlorine atom, and di nitrobenzene with two equal or two different radicals having a basic reaction. Compound No. 70 revealed a marked in vitro activity against fungi (Trichophyton; Microsporum, Candida albicans). Other nitro compounds such as bis mono and bis dinitrobenzene derivatives likewise showed a systemic action against E. histolytica, viruses and, in particular, carcinoma (Crocker's sarcoma 180, Ridgway's osteosarcoma). Oxygen and sulfur analogue compounds as well as compounds produced by reduction also possessed a distinct activity against E. histolytica and viruses. On the basis of the present results, the dinitrobenzenes substituted with two radicals having a basic reaction include a number which have in common a recognizable structure/activity relationship in respect to E. histolytica, Schistosoma mansoni and different types of viruses. The activity against viruses in this class of compounds is probably due to an increased interferon production in the host animal. Whether the mechanism of action is the same against E. histolytica or Schistosoma mansoni has not been determined so far. A tumorigenic effect was observed mainly in those di nitrobenzenes which are classed as alkylating compounds. Because of the small chemotherapeutic index, the trials were not continued with the most effective compounds mentioned.