4444-26-2

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4,5,6-Benzenehexamine-3HCl is used as a reagent in the preparation of 2-(benzimidazol-2-yl)quinoxalines, which are selective antagonists at human A1 and A3 adenosine receptors. These antagonists have potential applications in the treatment of various diseases, such as asthma, chronic obstructive pulmonary disease (COPD), and other conditions related to adenosine receptor activity.
Used in Chemical Synthesis:
Benzenehexamine-3HCl can be used as a building block or intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its hexaamine structure allows for multiple points of attachment and functionalization, making it a versatile starting material for the development of new molecules with specific properties and applications.
Used in Research and Development:
Due to its unique chemical structure and properties, 1,2,3,4,5,6-Benzenehexamine-3HCl can be employed in research and development for the exploration of new chemical reactions, mechanisms, and applications. It can serve as a model compound for studying the reactivity of amine groups and their interactions with other molecules, as well as for testing new synthetic methods and techniques.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 3904, 1986 DOI: 10.1021/jo00370a032

Upstream product

• 59127-54-7 benzo<1,2-c:3,4-c':5,6-c''>tris<1,2,5>thiadiazole 
• 108-70-3 1,3,5-trichlorobenzene 
• 100-01-6 4-nitro-aniline 
• 2631-68-7 1,3,5-trichloro-2,4,6-trinitrobenzene 
• 3058-38-6 2,4,6-triamino-1,3,5-trinitrobenzene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 114396-17-7 dodeca-N-methyl-benzenehexaylhexaamine 
• 79790-37-7 1,4,5,8,9,,12-hexaazatriphenylene 
• 129012-12-0 2,3-Diphenyl-1,4,5,8,9,12-hexaazatriphenylene 
• 129012-13-1 2,3,6,7-Tetraphenyl-1,4,5,8,9,12-hexaazatriphenylene 
• 96355-63-4 1,2,5,6,9,10-hexaphenylbenzo<1,2-b:3,4-b':5,6-b>tripyrazine 
• 114396-24-6 1,3,5-tris(ethylmethylamino)-2,4,6-tris(dimethylamino)benzene 
• 96380-81-3 2,3,6,7,10,11-Hexakis(4-pentylphenyl)dipyrazino<2,3-f:2',3'-h>chinoxalin 
• 96355-66-7 2,3,6,7,10,11-Hexakis(trans-4-heptylcyclohexyl)dipyrazino<2,3-f:2',3'-h>chinoxalin 
• 96355-65-6 2,3,6,7,10,11-Hexakis(4-nonylphenyl)dipyrazino<2,3-f:2',3'-h>chinoxalin 
• 96355-64-5 2,3,6,7,10,11-Hexakis(4-methoxyphenyl)dipyrazino<2,3-f:2',3'-h>chinoxalin 
• 92187-32-1 hexakis(chloroacetamido)benzene 
• 129012-15-3 2,3,7,8-Tetraphenyl-5,10-diamino-1,4,6,9-tetraazaanthracene 
• 129012-14-2 2,3-Diphenyl-5,6,7,8-tetraaminoquinoxaline 
• 114422-56-9 pentakis(dimethylamino)aniline 

Relevant academic research and scientific papers

Hexaazatriphenylene-Based Hydrogen-Bonded Organic Framework with Permanent Porosity and Single-Crystallinity

Hydrogen-bonded organic frameworks (HOFs) have drawn unprecedented interest because of their high crystallinity as well as facile process for construction, deconstruction, and reassembly arising from reversible bond formation-dissociation. However, struct

Construction of isostructural hydrogen-bonded organic frameworks: limitations and possibilities of pore expansion

The library of isostructural porous frameworks enables a systematic survey to optimize the structure and functionality of porous materials. In contrary to metal-organic frameworks (MOFs) and covalent organic frameworks (COFs), a handful of isostructural f

A molecular claw: A dynamic cavitand host

Up for grabs: A modular receptor comprises a hexaazatriphenylene "platform" and three imide residues on its concave side carrying flexible alkane chains. The chains not only populate the host's cavity but can also extend and can grab an appropriately size

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.

Docking Strategy To Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area

Enhancing thermal and chemical durability and increasing surface area are two main directions for the construction and improvement of the performance of porous hydrogen-bonded organic frameworks (HOFs). Herein, a hexaazatriphenylene (HAT) derivative that possesses six carboxyaryl groups serves as a suitable building block for the systematic construction of thermally and chemically durable HOFs with high surface area through shape-fitted docking between the HAT cores and interpenetrated three-dimensional network. A HAT derivative with carboxybiphenyl groups forms a stable single-crystalline porous HOF that displays protic solvent durability, even in concentrated HCl, heat resistance up to 305 °C, and a high Brunauer–Emmett–Teller surface area [SA(BET)] of 1288 m2 g?1. A single crystal of this HOF displays anisotropic fluorescence, which suggests that it would be applicable to polarized emitters based on robust functional porous materials.

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 hexaazatriphenylene-based organogel that responds to silver(I) with high selectivity under aqueous condition

A hexaazatriphenylene (HAT)-based gelator was developed. It exhibits excellent gelation ability. The resulting organogel shows very high selectivity toward Ag+ ion under aqueous condition in the form of gel-sol transformation. The mechanism of such transformation was also investigated through UV-vis spectroscopy and powder X-ray diffraction.

Synthesis and electrochemical and theoretical studies of V-shaped donor-acceptor hexaazatriphenylene derivatives for second harmonic generation

In this article we describe novel synthetic strategies toward well-defined disubstituted conjugated hexaazatriphenylene (HAT) derivatives. The systems are designed as novel V-shaped chromophores displaying C2 symmetry suitable for nonlinear optical investigations. Different donor moieties and linkers have been used in order to tune the electrochemical properties as well as the absorption spectra of the novel HAT derivatives. μβ values as high as 1010 × 10-48 esu have been obtained for a derivative containing the electron-rich dibutylamino moiety. Theoretical calculations have been performed showing a reasonable agreement with the experimental results and supporting the two-dimensional NLO character of these chromophores.