489-98-5

Usage

InChI:InChI=1/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2

Upstream product

• 98-50-0 p-aminophenylarsonic acid 
• 932-90-1 syn-benzaldehyde oxime 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 64-17-5 ethanol 
• 99-35-4 1,3,5-trinitrobenzene 
• 857592-15-5 N-methyl-2,4,6-trinitro-N-nitroso-aniline 
• 14677-67-9 phenyl-picryl sulfone 
• 18631-76-0 N-Hydroxy-2,4,6-trinitroaniline 
• 21416-60-4 naphthalene; compound with 2-chloro-1,3,5-trinitro-benzene 
• 88-89-1 2,4,6-Trinitrophenol 
• 57-13-6 urea 
• 91-66-7 N,N-diethylaniline 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 110533-91-0 furan-2-carboxylic acid-(2,4,6-trinitro-anilide) 
• 89488-72-2 benzene-1,2,3,5-tetrayltetraamine 
• 609-24-5 2,4,6-triaminophenol 
• 4591-46-2 trinitrophenylnitramine 
• 89533-32-4 5-nitro-benzene-1,2,3-triyltriamine 
• 132752-72-8 1-Picrylazo-[2]naphthol 
• 88-89-1 2,4,6-Trinitrophenol 
• 3698-53-1 1,2,3,5-tetranitrobenzene 
• 131-73-7 Dipikrylamin 
• 3694-51-7 2-amino-3,5-dinitrophenylamine 
• 97661-74-0 benzoic acid-(2,4,6-trinitro-anilide) 
• 5457-35-2 N-picryl-dibenzamide 
• 84615-01-0 N-picryl-phthalimide 
• 56205-32-4 2-thioxo-3-(2,4,6-trinitro-phenyl)-thiazolidin-4-one 

Relevant academic research and scientific papers

Insights into the synthesis of hexaaminobenzene hydrochloride: An entry to hexaazatriphenylenes

Polycyclic N-heteroaromatic systems and particularly, the dipyrazino[2,3-f:2′,3′-h]quinoxaline also known as 1,4,5,8,9,12-hexaazatriphenylene (HAT) displays very useful optoelectronic properties. Its synthesis through condensation of functionalized 1,2-diketones and hexaaminobenzene is often applied on laboratory scale. Hexaaminobenzene could be prepared from 4-nitroaniline but, despite its many applications, the experimental protocol is not trivial and should by carefully controlled in each step. In this work, we presented an efficient and reproducible 4 steps synthesis of hexaaminobenzene hydrochloride and a comprehensive analysis of reactions conditions and products formed in all synthetic steps. As evidence, this aromatic polyamine was effectively condensed with 1,2-di(4-bromophenyl)-1,2-ethanedione affording a synthetically versatile HAT derivative for the application in the design of organic materials.

Ultrathin two-dimensional π-d conjugated coordination polymer Co3(hexaaminobenzene)2 nanosheets for highly efficient oxygen evolution

Organic two-dimensional (2D) materials with unique optic-electronic properties are attracting great interest for application in functional electronic devices. However, low electronic conductivity and poor stability still are major defects of 2D organic systems. Herein, we demonstrated ultrathin 2D conductive cobalt-hexaaminobenzene metal-organic coordination polymer nanosheets (Co-HAB-NSs) with a thickness of ～4.5 nm. The as-prepared Co-HAB-NSs exhibit a low overpotential (310 mV @ 10 mA cm-2) and high durability in 1 M KOH. The experimental and computational results show that the high electrocatalytic activity is ascribed to the enhanced electrochemically active surface area as well as the dense and stable catalytic active sites of Co-HAB-NSs.

Signature of metallic behavior in the metal-organic frameworks M3(hexaiminobenzene)2 (M = Ni, Cu)

The two-dimensionally connected metal- organic frameworks (MOFs) Ni3(HIB)2 and Cu3(HIB)2 (HIB = hexaiminobenzene) are bulk electrical conductors and exhibit ultraviolet-photoelectron spectroscopy (UPS) signatures expected of metallic solids. Electronic band structure calculations confirm that in both materials the Fermi energy lies in a partially filled delocalized band. Together with additional structural characterization and microscopy data, these results represent the first report of metallic behavior and permanent porosity coexisting within a metal-organic framework.

Erratum: Hexaaminobenzene as a building block for a family of 2D coordination polymers (Journal of the American Chemical Society (2017) 139 (19-22) DOI: 10.1021/jacs.6b09889)

Supporting Information, page S2. We regret that we inadvertently omitted a safety note stating that 2,4,6-trinitroaniline (TNA) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) are very sensitive and highly explosive. They should be handled with extreme caution. An updated Supporting Information file with this note in place is provided.

Hexaaminobenzene as a building block for a family of 2D coordination polymers

A family of 2D coordination polymers were successfully synthesized through "bottom-up" techniques using Ni2+, Cu2+, Co2+, and hexaaminobenzene. Liquidliquid and air-liquid interfacial reactions were used to realize thick (～1-2 μm) and thin (10 nm) stacked layers of nanosheet, respectively. Atomic-force microscopy and scanning electron microscopy both revealed the smooth and flat nature of the nanosheets. Selected area diffraction was used to elucidate the hexagonal crystal structure of the framework. Electronic devices were fabricated on thin samples of the Ni analogue and they were found to be mildly conducting and also showed back gate dependent conductance.

A Stable Hexakis(guanidino)benzene: Realization of the Strongest Neutral Organic Four-Electron Donor

The growing demand for efficient batteries has stimulated the search for redox-active organic compounds with multistage redox behavior, as materials with large charge capacity. Herein we report the synthesis and properties of the first hexakis(guanidino)benzene derivative: a strong neutral organic electron donor with reversible multistage redox behavior and a record low redox potential for donation of four electrons. Detailed structural and spectroscopic characterization of three redox states (0, +2, and +4) reveal its unique electronic features. Despite its nitrogen richness, the compound is thermally robust and can be readily purified by sublimation.

Method of synt hesizing Hexaaminobenzene

The present invention relates to a synthesis method for hexaaminobenzene trihydrochloride. The present invention solves existing problems that large-scale production is impossible due to instability of hexaaminobenzene by converting hexaaminobenzene into hexaaminobenzene hydrochloride and enables large-scale production of stable high-purity hexaaminobenzene with improved processing efficiency. Additionally, the present invention is able to be applied to various fields since HAB synthesized according to the present invention is able to be an excellent intermediate for discotic liquid crystal, a compound with low resistance to the transfer of hole and electron to be used in organic electron fields, a marcrocyclic compound, a hexaazatriphenylene based donor-acceptor molecule, an electron deficiency electron extension system, a ferromagnetism organic salt and cadmium (II) for a fluorescent sensor.

A novel N-N bond cleavage in 1,5-diaminotetrazole: Synthesis and characterization of 5-picrylamino-1,2,3,4-tetrazole (PAT)

The reaction of 1,5-diaminotetrazole with picryl chloride (PiCl) forms 5-picrylamino-1,2,3,4-tetrazole (PAT) rather than the expected 1-picrylamino-5-amino-1,2,3,4-tetrazole or 5-picrylamino-1-amino-1,2,3,4- tetrazole. The structure of PAT was confirmed by single-crystal X-ray diffraction. Some of the energetic properties of the synthesized compound were also studied.

Scalable synthesis of pure and stable hexaaminobenzene trihydrochloride

Synthesis of hexaaminobenzene (HAB) in pure and stable form has remained as an important challenge for a long time, since it is a fascinating synthon for the synthesis of aromatic nitrogenous compounds having many interesting applications. Here, we report an improved synthesis of pure and stable HAB form using modified catalytic hydrogenation in aqueous acidic medium. The structure of needle-shaped HAB crystals was confirmed by single-crystal X-ray diffraction study. The synthetic protocol could thus be a simple, but efficient for the large-scale synthesis of highly pure and stable HAB. Georg Thieme Verlag Stuttgart New York.

Synthesis of N-(5,7-diamino-3-phenyl-quinoxalin-2-yl)-3,4,5-substituted anilines and N-[4[(5,7-diamino-3-phenylquinoxalin-2-yl)amino]benzoyl]-l-glutamic acid diethyl ester: Evaluation of in vitro anti-cancer and anti-folate activities

Several diamino quinoxalines were designed, synthesized and evaluated as anti-tumor agents. Two compounds showed the most potent cytotoxic activities against the leukemia CCRF-CEM cell line (GI50 50 = 0.03 μM), respectively, with comparable/better activities than Methotrexate (MTX). Docking calculations of the complexes of hDHFR with the most active compounds identified the binding mode of the described molecules with respect to MTX.