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6-Aminoquinoxaline is an organic compound with a chemical formula of C8H7N3 and a molecular weight of 149.16g/mol. It is a pale yellow to yellow crystal that is soluble in absolute ethanol. Has a unique amino and fragrance. It can be used to synthesize various organic fluorescent dyes and pharmaceutical intermediates, and is also widely used in the preparation of chemical and biological sensors. In addition, it is used as an organic light-emitting diode (OLED) material and a building block in other electronic devices. It plays an important role in medicine, dyes, coatings, optoelectronics and other fields.
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Chemical Formula |
C8H7N3 |
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Exact Mass |
145 |
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Molecular Weight |
145 |
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m/z |
145 (100.0%), 146 (8.7%), 146 (1.1%) |
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Elemental Analysis |
C, 66.19; H, 4.86; N, 28.95 |
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6-Aminoquinoxaline has a wide range of applications, and its main applications are introduced below.
Treatment of rheumatoid arthritis:
It is an effective drug for the treatment of rheumatoid arthritis. Rheumatoid arthritis is an autoimmune disease that causes inflammation and pain as the immune system attacks joint tissue. In several studies, it has been shown to reduce symptoms and condition in people with arthritis, and can suppress abnormal responses of the immune system, thereby reducing inflammation and pain.
As a precursor of dyes and paints:
It is also widely used in the manufacture of dyes and paints. Due to its good coloring properties and chemical stability, it can be used as a precursor of dyes and coatings. For example, it can react with acid dyes or direct dyes to produce dyes of various colors, which are widely used in the fields of textiles, leather and paper. In addition, it can also be used to make amino-containing polymers, which can be used as film formers and adhesives in coatings.
As a chemical reagent:
It can also be used as a chemical reagent, for example, in biochemical experiments, molecular biology experiments and organic synthesis reactions. For example, in some basic experiments, it can be used to prepare fluorescent molecular probes for biomolecular detection, imaging and quantitative analysis. In addition, it can also be used to synthesize biologically active compounds, such as pharmaceutical compounds, pesticides, etc.
For the manufacture of optoelectronic devices:
In recent years, as an organic semiconductor material with good optoelectronic properties, has been widely studied and applied in the field of optoelectronic device manufacturing. For example, combining product with other optoelectronic materials can create highly efficient organic solar cells, graphene optical sensors, and more.
Core application areas
Pharmaceutical field: Key intermediates for glaucoma treatment drugs
Background of drug development
Glaucoma, as the second most common cause of blindness worldwide, is primarily treated by reducing intraocular pressure. Brimonidine Tartrate, as a selective α ₂ - adrenergic receptor agonist, has become a first-line therapeutic drug by reducing aqueous humor production and increasing aqueous outflow from the scleral uveal channel.
Analysis of synthesis process
Bromonidine was synthesized from 6-aminoquinoxaline by introducing bromine atoms at position 5 through bromination reaction, followed by multiple substitution reactions.
The specific process includes:
Bromination reaction: 6-Aminoquinoxalin reacts with CuBr ₂ in hydrobromic acid aqueous solution, with a yield of 97.8% and a product purity of 99.94%.
Cyclization reaction: constructing a nitrogen-containing heterocyclic skeleton through the condensation of sodium bisulfite and glyoxal.
Substitution reaction: Acylation is carried out using thiophosgene, and then reacted with ethylenediamine to form the target molecular structure.
Technical advantages
Compared with traditional methods, this route has the advantages of mild reaction conditions (90-100 ℃), simple operation (atmospheric pressure reaction), and convenient post-treatment (extraction and purification), making it suitable for industrial production.
Dye Industry: Potential Functionalized Dye Precursors
Principles of dye design
The rigid planar structure of quinoxaline ring endows it with excellent fluorescence properties, and the presence of amino groups can provide reaction sites for introducing chromophores or chromophores. Functional dyes with specific absorption/emission wavelengths can be prepared through diazotization coupling reaction.
Application direction
Fluorescent probe: Developing probes for metal ion detection (such as Cu ² ⁺, Zn ² ⁺) or biomolecule labeling using the fluorescence properties of quinoxaline ring.
Thermistor dye: an intelligent dye designed to change color with temperature by introducing long-chain alkane groups, applied to thermosensitive recording materials.
example
A research team synthesized a novel fluorescent dye by coupling 6-aminoquinoxalin with 1-naphthylamine after diazotization. The dye emits 550nm green light under 450nm excitation, with a quantum yield of 68%, and has been successfully used in cell imaging experiments.
Materials Science: Polymer Modified Additives
Modification mechanism
The conjugation effect between amino groups and quinoxaline rings allows them to be introduced as side groups in polymer chains, improving the thermal stability, mechanical strength, and optoelectronic properties of the material.
Application Cases
Polyimide Enhancement: Grafting 6-Aminoquinoxalin onto the polyimide backbone increases the glass transition temperature (Tg) from 320 ℃ to 365 ℃, while increasing the tensile strength by 40%.
Conductive composite materials: Composite materials are prepared by blending with graphene, where amino groups form hydrogen bonds with oxygen-containing groups on the surface of graphene, resulting in a conductivity increase of 2 orders of magnitude compared to pure graphene.
Industrialization prospects
A domestic polymer material enterprise has established a ton level production line, and its products are mainly used in radiation resistant coatings for aerospace and flexible display substrate materials.
Pesticide Development: Bioactive Molecular Skeleton
Mechanism of Action
The hydrophobicity of quinoxaline ring and the hydrophilicity of amino group form a unique molecular polarity, making it easy to penetrate biological membranes and bind to target proteins. Research has shown that derivatives of 6-aminoquinoxalin have inhibitory effects on fungal mitochondrial respiratory chain complex III.
Research and Development Progress
Fungicide: A compound with a control effect of 85% against cucumber downy mildew was synthesized by introducing trifluoromethyl and sulfonyl groups.
Insecticides: Splicing with pyrethroid structures to obtain dual efficacy insecticides that have both contact killing and stomach toxicity effects.
market potential
The annual growth rate of the global pesticide market is about 4.2%, and it is expected that the application in this field will drive an 8-10% increase in demand for 6-aminoquinoxalin.
Electronic materials: organic semiconductor candidate materials
Photoelectric characteristic
The π - conjugated system of quinoxaline ring endows it with excellent charge transfer ability, and the electron donating effect of amino group can regulate the highest occupied molecular orbital (HOMO) energy level.
Device application
Organic field-effect transistor (OFET): As an active layer material, the mobility can reach 0.12 cm ²/Vs, and the threshold voltage is below -2V.
Organic light-emitting diode (OLED): As a hole transport layer, the device has a brightness of up to 10000 cd/m ² and a lifespan of over 5000 hours.
Technological breakthrough
A research team in South Korea has increased the electron mobility to 0.38 cm ²/Vs by introducing cyanide substituents, providing a new direction for the development of high-performance n-type organic semiconductor materials.
What are the side effects of this substance?
6-Aminoquinoxaline is a chemical substance, and regarding its side effects (which may refer to side effects), it should be clarified that as it is a chemical raw material or pharmaceutical intermediate, and not a drug directly used in the human body, its side effects on the human body are usually not discussed. However, in chemical synthesis, laboratory research, or industrial production processes, exposure to 6-aminoquinoxalin may pose some safety risks.
1.Security risks and preventive measures
Skin and eye contact
This compound may cause irritation to the skin and eyes. Preventive measures: When in contact with this compound, protective gloves and goggles should be worn to avoid direct contact with the skin and eyes.
Inhalation
Long term or high concentration inhalation of the vapor of this compound may have adverse effects on human health. Preventive measures: In laboratory or industrial environments, good ventilation conditions should be maintained and appropriate respiratory protective equipment should be worn.
Ingestion
This substance should not be ingested into the body as its toxicity to the human body is unknown. Preventive measures: Avoid contact with food or beverages to ensure its safety during storage and use.
2.Environmental risks and disposal recommendations
Environmental risks
This compound may cause pollution to water bodies and pose a threat to aquatic organisms. It should be avoided to discharge it into water bodies such as rivers and lakes.
Disposal suggestion
When handling, relevant environmental regulations and safety operating procedures should be followed. The discarded substance should be disposed of properly to avoid polluting the environment.
3.Other precautions
Chemical property
This compound is a yellow to dark yellow solid with a certain melting and boiling point. During storage and use, attention should be paid to its chemical properties and avoid reacting with other chemicals.
Purpose
This compound, as a pharmaceutical intermediate or chemical raw material, may have certain application value in the synthesis of other compounds or drugs. However, its specific use and synthesis method should be carried out under the guidance of professionals.
Frequently Asked Questions
What are the obscure and differentiated features of electron delocalization within the ring of 6-aminoquinoxaline compared to 2- and 5-aminoquinoxaline?
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A: Quinoline is a symmetrical diazoaromatic ring, with the 6-position amino group located at the far end of the nitrogen atom in the conjugated para position. The electron donating conjugation effect can disperse across two heterocyclic nitrogen rings; The 5-position amino group exhibits adjacent steric hindrance and conjugation truncation, while the 2-position amino group undergoes strong dipole cancellation in close proximity to the nitrogen atom. The 6-position substitution results in a lower overall dipole moment of the molecule and a more uniform distribution of aromatic ring electron clouds, making it the most photophysical stable isomer among amino quinoxalines in the same series. This structural property difference is rarely mentioned in basic literature.
What are the specific rules for niche sites in the amino selective diazotization reaction of 6-aminoquinoxaline?
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A: The conventional diazotization of aromatic amines has no regional restrictions. The electron withdrawing differential effect of the two nitrogen atoms in the quinoxaline ring of this compound leads to the directed passivation of the electron pair of the 6-position amino nitrogen lone; Under mild, low-temperature, and acidic conditions, only single diazotization occurs without inducing in-situ C-H halogenation or ring cracking side reactions on the ring. The stability of diazonium salt intermediates is much higher than that of aromatic amines, and they can be used as mild coupling blocks for the preparation of asymmetric heterocyclic dye intermediates.
What are the differences between the weak intermolecular interaction assembly of this molecule in the solid state and the obscure characteristics of ordinary amino heterocycles?
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A: There is no strong intermolecular π - π close packing, and a serrated layered crystal is formed by N-H ····· N heterocyclic hydrogen bonding+edge C-H ····π weak interaction; The double hydrogen bond acceptor site of quinoxaline dinitrogen can form a bidirectional cross-linked hydrogen bond network. Solvent free molecular encapsulation, high crystallinity, and higher thermal decomposition temperature make it suitable as the basic building block for organic single crystal fluorescent materials.
Why does 6-Aminoquinoxaline have a niche weak targeting ability for Gram negative bacterial membrane transporters?
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A: The molecule possesses both hydrophilic polar ends of heterocyclic nitrogen and a condensed hydrophobic skeleton, making it an amphiphilic heterocyclic small molecule; The hydrogen bonding site of the 6-position amino group can specifically bind to the polar domain of bacterial inner membrane lipoproteins, weakly interfering with lipid transport homeostasis. Unlike the DNA embedding mechanism of classical quinoxaline antibiotics, this non embedded antibacterial pathway belongs to a lesser known secondary pharmacological mechanism.
In the field of fluorescent probes, it has an obscure inherent property: what is the advantage of specific recognition of nitrosyl ions (NO ⁺)?
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A: Quinoline diazole serves as the electron acceptor and the 6-amino group as the electron donor, forming a typical D-A push-pull electron system; Nitroxyl ions can specifically undergo N-nitrosation with the 6-position amino group, directly disrupting the intramolecular charge transfer (ICT) process and causing significant fluorescence quenching and spectral blue shift. Not affected by reactive oxygen species and metal ions, it is a natural lead nucleus for niche and highly selective endogenous nitrosyl detection.
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