3244-54-0

Basic information

• Product Name: 3,6-DINITRO-9H-CARBAZOLE
• Synonyms: 3,6-DINITRO-9H-CARBAZOLE;3,6-DINITROCARBAZOLE
• CAS NO: 3244-54-0
• Molecular Formula: C₁₂H₇N₃O₄
• Molecular Weight: 257.20168
• EINECS: 221-814-4
• Mol File: 3244-54-0.mol

Chemical Properties

• Melting Point: 365-367 °C
• Boiling Point: 537.2°Cat760mmHg
• Flash Point: 278.7°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 4.54E-11mmHg at 25°C
• Refractive Index: 1.819
• PKA: 13.43±0.30(Predicted)
• CAS DataBase Reference: 3,6-DINITRO-9H-CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DINITRO-9H-CARBAZOLE(3244-54-0)
• EPA Substance Registry System: 3,6-DINITRO-9H-CARBAZOLE(3244-54-0)

Safety Data

• Hazardous Substances Data: 3244-54-0(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Production:
3,6-DINITRO-9H-CARBAZOLE is used as a precursor in the production of dyes and pigments, contributing to the development of colorants for various applications.
Used in Explosive Manufacturing:
This chemical compound is utilized in the manufacturing of certain explosives, leveraging its properties to enhance the performance of these products.
Used in Pharmaceutical Industry:
3,6-DINITRO-9H-CARBAZOLE serves as a precursor in the production of pharmaceuticals, potentially contributing to the development of new medications.
Used in Organic Light-Emitting Diodes (OLEDs):
Due to its strong electron-accepting capabilities, 3,6-DINITRO-9H-CARBAZOLE is being studied for its potential use in OLEDs, where it could improve the efficiency and performance of these devices.
Used in Photovoltaic Devices:
3,6-DINITRO-9H-CARBAZOLE is also being explored for its application in photovoltaic devices, where it could enhance the conversion of light into electricity, improving the overall efficiency of solar panels.

InChI:InChI=1/C12H7N3O4/c16-14(17)7-1-3-11-9(5-7)10-6-8(15(18)19)2-4-12(10)13-11/h1-6,13H

Upstream product

• 86-74-8 9H-carbazole 
• 2788-23-0 9-nitroso-9H-carbazole 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 64-19-7 acetic acid 
• 574-39-0 9-acetylcarbazole 
• 5393-41-9 3-nitro-9-nitroso-carbazole 
• 3077-85-8 3-Nitro-carbazol 

Downstream Products

• 50717-02-7 N-ethyl-3,6-diamino-carbazole 
• 1246212-61-2 C₃₅H₂₆Cl₂N₅O₆^(1-)*K⁽¹⁺⁾ 
• 1246212-53-2 C₂₈H₁₉Cl₂N₄O₆^(1-)*K⁽¹⁺⁾ 
• 1246212-60-1 C₃₇H₂₉Cl₂N₅O₈ 
• 1246212-52-1 C₃₀H₂₂Cl₂N₄O₈ 
• 1246212-57-6 C₃₃H₂₁Cl₂N₄O₆^(1-)*K⁽¹⁺⁾ 
• 1246212-56-5 C₃₅H₂₄Cl₂N₄O₈ 
• 1246212-62-3 C₃₆H₃₁N₅O₆ 
• 1246212-54-3 C₂₉H₂₄N₄O₆ 
• 1246212-58-7 C₃₄H₂₆N₄O₆ 
• 1246212-63-4 C₂₉H₂₅N₅O₆ 
• 1246212-55-4 C₂₂H₁₈N₄O₆ 
• 1246212-59-8 C₂₇H₂₀N₄O₆ 
• 1246212-65-6 C₂₇H₁₇Cl₂N₄O₆^(1-)*K⁽¹⁺⁾ 

Relevant articles and documents

Synthesis and memory characteristics of novel soluble polyimides based on asymmetrical diamines containing carbazole

Two novel asymmetrical carbazole-based diamines 9-(2-(1,1′-binaphthyl-4-yl)benzyl)-9H-carbazole-3,6-diamine (BNBCD) and 9-((4′-(9H-carbazol-9-yl)biphenyl-2-yl)methyl-9H-carbazole-3,6-diamine (CBMCD) were synthesized. A series of novel soluble aromatic polyimides were prepared from these diamines by poly-condensation with Pyromelitic dianhydride (PMDA) and 2,2′,3,3′-biphenyl tetracarboxylic dianhydride (BPDA) via a two-step procedure. The resulting polymers were fully characterized, they exhibited excellent organosolubility and high thermal stability with the temperature of 5% weight loss under nitrogen atmosphere over 400°C. Resistive switching devices with the configuration of Al/polymer/ITO were constructed from these polyimides by using conventional solution coating process. The memory devices based on PI-a, PI-b and PI-c exhibited a flash type memory capability, whereas the PI-d presented a write once read many times (WORM) memory capability.

Synthesis and fluorescence properties of 3,6-diaminocarbazole-modified pyrrolidinyl peptide nucleic acid

This work aims to explore a new clickable carbazole-based fluorescent label, its incorporation into pyrrolidinyl peptide nucleic acid (acpcPNA), and the interactions between the labeled PNA probe and DNA by fluorescence spectrophotometry and molecular dynamics simulation. A carbazole derivative, namely 3,6-diaminocarbazole (DAC), was synthesized and incorporated into the internal and terminal positions of azide-modified acpcPNA via a sequential reductive alkylation and click reaction previously developed by our group. The DAC-modified acpcPNA can form a stable hybrid with complementary DNA with somewhat lower stability compared to unmodified acpcPNA. Most importantly, the DAC-modified acpcPNA exhibits a remarkable fluorescence increase in the presence of DNA (up to 35.5 fold with complementary DNA). Non-complementary as well as single mismatched DNA targets gave a smaller fluorescence increase (1.1 to 18.6 fold), and the discrimination could be further improved by increasing the temperature to dissociate the mismatched hybrids. Molecular dynamic simulations revealed that the DAC interacts with adjacent nucleobases in single stranded PNA, resulting in quenching of the fluorescence signal. When the PNA formed a hybrid with DNA, the DAC was pushed away from the duplex, resulting in a fluorescence increase. Thus, the DAC-labeled acpcPNA is a potential candidate as a self-reporting probe for determination of DNA sequences.

Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of c-myc G-quadruplex binding ligands

A series of 1,8-dipyrazolcarbazole (DPC) derivatives (6a-6d, 7a-7d) designed as G-quadruplex ligands have been synthesized and characterized. The FRET-melting and SPR results showed that the DPC derivatives could well recognize G-quadruplex with strong discrimination against the duplex DNA. In addition, the DPC derivatives showed much stronger stabilization activities and binding affinities for c-myc G-quadruplex rather than telomeric G-quadruplex. Therefore, their interactions with c-myc G-quadruplex were further explored by means of CD spectroscopy, PCR-stop assay, and molecular modeling. In cellular studies, all compounds showed strong cytotoxicity against cancer cells, while weak cytotoxicity towards normal cells. RT-PCR assay showed that compound 7b could down-regulate c-myc gene expression in Ramos cell line, while had no effect on c-myc expression in CA46 cell line with NHE III1 element removed, indicating its effective binding with G-quadruplex on c-myc oncogene in vivo.

Square [5]molecular necklace formed from cucurbit[8]uril and carbazole derivative

The formation of square 5-member molecular necklace ([5]MN) is presented by utilizing the host-guest recognition-driven self-assembly between CB[8] and carbazole derivative 1·2Cl-, which bears two 4,4′-bipyridin-1-ium (BP) arms with a orthogonal geometry. The self-assembly and stimuli-responsive behaviors of square [5]MN are comprehensively investigated by NMR (1H, COSY, NOSEY, and DOSY), UV-vis, DLS, and SEM methods.

Carbazole triamine derivative and preparation method and application thereof

The invention discloses a carbazole triamine derivative and a preparation method thereof. The carbazole triamine derivative has a structure shown in the following formula. The preparation method of the carbazole triamine derivative is easy to operate, raw materials are easy to obtain, the price is low, the purity is extremely high, and the reaction yield is very high; the carbazole triamine derivative prepared by the method has wide application prospects in the fields of medicine, biology, luminescent materials and the like.

Diversity of metal-organic macrocycles assembled from carbazole based ligands with different lengths

A series of carbazole based ligands with different lengths were assembled with nickel ions to construct metal-organic macrocycles. High-resolution mass spectrometry and ion mobility-mass spectrometry have been used to analyse the resulting MnLn assembly coexisting in solution. Combining with the structural analysis of their solid confirmation, it was revealed that the diversity of the metal-organic macrocycles was increased with the flexibility of the ligands.

Carbazole as Linker for Dinuclear Gadolinium-Based MRI Contrast Agents

Ligands able to complex two gadolinium ions have been synthesized and characterized in view of the ability of the complexes to increase the spin relaxation of water protons. All ligands are based on the heptadentate diethylenetriaminetetraacetic acid (DTTA) chelator and carbazole as a rigid linker. Depending on the derivatization on the nitrogen atom of the five-membered ring, the compounds form small aggregates in aqueous solution, self-assemble to form micelles or bind to human serum albumin. In all cases, this leads to a marked increase in 1H relaxivity at nuclear Larmor frequencies between 20 and 60 MHz. Water exchange on the gadolinium ions as measured by 17O NMR relaxation is fast enough not to limit relaxivity. 1H nuclear magnetic relaxation dispersion profiles were also measured and analyzed using Solomon–Bloembergen–Morgan theory including Lipari–Szabo treatment to include internal motion or anisotropic rotation.

9-(2'-aryl benzyl)-3, 6-diamino carbazole compound and preparation method thereof

The invention provides a 9-(2'-aryl benzyl)-3, 6-diamino carbazole compound and a preparation method thereof. The compound is obtained by the following steps: firstly performing nitrification for carbazole, allowing a nitrification product to react with bromobenzyl bromide, adding a reducing agent to generate 9-(2'-bromobenzyl)-3,6-diamino carbazole, and finally allowing 9-(2'-bromobenzyl)-3,6-diamino carbazole to perform Suzuki reaction with various conjugated arylboronic acids to obtain the compound. The compound is simple in synthetic procedures and high in yield; an asymmetric structure is formed by introducing large aromatic side groups by virtue of Suzuki reaction, the regularity of a monomer is destroyed, and when the diamino monomer is polymerized with an anhydride monomer to form a polymer, the polymer is arranged in a non-coplanar manner by virtue of the large aromatic side groups, so that the solubility and optical properties of a synthetic material can be improved.

Novel functional triamine monomer containing carbazole structure and preparation method and application thereof

The invention discloses a novel functional triamine monomer containing a carbazole structure and a preparation method and application thereof. Starting from carbazole, the novel functional triamine monomer containing carbazole is prepared through a nitration reaction, a Ullmann coupling reaction, a reduction reaction and other reactions; or starting from mono-halogenated carbazole or dihalogenated carbazole, the novel functional triamine monomer containing carbazole is prepared through a Ullmann coupling reaction, a Suzuki reaction, a reduction reaction and other reactions. The novel functional triamine monomer containing carbazole is simple in synthesis method and technology, high in yield and easy to purify, and therefore the novel functional triamine monomer containing carbazole is suitable for industrial production. The novel functional triamine monomer can be used for synthesizing hyperbranched and functional polyamide, polyimide, polyamide imide, polyester imide and other polymers.

Synthesis, characterization and pharmacological evaluation of some novel 3,6-dinitrocarbazole derivatives

N-Mannich bases of newly synthesized carbazole compounds were synthesized from carbazole by reacting with series of aldehydes i.e., formaldehyde and acetaldehyde and the various secondary amines. Synthesized compounds were characterized by spectral studies and evaluated for antibacterial activities by cup and plate method. The statistical analysis was done by students t test and the values were expressed as mean ± SEM.