3-Amino-9-ethylcarbazole CAS 132-32-1

3-Amino-9-ethylcarbazole is an organic compound with the chemical formula C14H15N3, CAS 132-32-1, and a relative molecular weight of 225.29 g/mol. Usually present as a light yellow to brownish yellow solid. It can exist in the form of crystalline powder. It has a certain solubility in common organic solvents such as ethanol, dichloromethane, chloroform, etc. It can be dissolved in many organic solvents, but its solubility is lower in non-polar solvents. Soluble in water, forming an alkaline solution. The pH value of its aqueous solution may be affected by its acid-base properties. The specific crystal structure can be analyzed through methods such as X-ray diffraction to understand the arrangement and spatial geometric configuration of molecules. It has multiple applications in chemical research and industrial fields. It is an important intermediate for the preparation of dyes, fluorescent agents, and organic electronic materials. In addition, it can also be used for organic synthesis reactions and the preparation of photosensitive materials.

3-Amino-9-ethylcarbazole (3AE-C) is an organic small molecule with broad application prospects and has important applications in the field of biological imaging.

1. Fluorescent probe:3AE-C has good fluorescence performance and can be used as a fluorescence probe for cell and tissue imaging. Its unique chemical structure allows it to have a wide absorption and emission wavelength range in the fluorescence spectrum, and exhibits relatively high quantum yields. This makes 3AE-C an excellent biomarker that can be used for fluorescence microscopy imaging, intracellular localization, and tracking.

2. Intracellular staining agents:Due to its hydrophilicity and cellular permeability, 3AE-C can be absorbed by cells and emit fluorescent signals within the cells. Therefore, 3AE-C can be used as an intracellular stain for observing cell activity, apoptosis, organelle labeling, and more. For example, by binding to specific molecules or targets within the cell, 3AE-C can be introduced into the cell to achieve visualization of specific cellular processes and biomolecules.

3. Biological tissue imaging:3AE-C has good tissue permeability and potential fluorescence imaging ability in living biological tissues. It can be applied to animal models through injection or local application to achieve in vivo imaging of biological tissues, such as mouse skin imaging, vascular imaging, etc. By combining with specific targets, 3AE-C can help researchers observe and study the function and structure of biological tissues.

4. Tumor diagnosis and treatment:Tumor imaging is an important part of clinical diagnosis and treatment. 3AE-C can serve as a fluorescent probe for early detection, localization, and evaluation of tumors. By targeting 3AE-C to tumor cells, fluorescence labeling of tumors can be achieved, providing important information in tumor imaging. In addition, combining treatment methods such as 3AE-C and photothermal therapy can also achieve precise treatment of tumors.

5. Neuroscience research:Due to the cell permeability and fluorescence imaging properties of 3AE-C in neural tissues, its application in neuroscience research has also received great attention.

3AE-C can serve as a neural marker for observing the morphology, connectivity, and function of neurons. In addition, 3AE-C can also be combined with other molecular probes, such as soluble polymers or fluorescent proteins, to achieve multi-parameter imaging of neural networks.3AE-C has broad application potential in the field of biological imaging. It can be used as a fluorescent probe for cell and tissue imaging, with good hydrophilicity, tissue permeability, and fluorescence performance. By combining with specific molecules within cells, localization, tracking, and microscopic observation of cells and tissues can be achieved. In addition, 3AE-C has also shown important application prospects in fields such as tumor diagnosis and treatment, neuroscience research, etc. It should be pointed out that specific applications need to be designed and optimized based on actual research objectives and conditions to achieve the best imaging results.

A common method for synthesizing 3-Amino-9-ethylcarbazole (3AE-C) in the laboratory is as follows:

1. Preparation of raw materials:

-9-Ethylcarbazole: obtained by reacting carbazole with 2-bromoethane.

-Ammonia (ammonia gas) or ammonia water: used to introduce amino groups.

2. Synthesis steps of 3AE-C:

This synthesis method involves two main steps: alkylation reaction and amination reaction.

Step 1: Alkylation reaction, introducing ethyl groups into the carbazole molecule.

Chemical equation:

C₁₂H₉N+C₂H₆BrNaO₃S → C₁₄H₁₃N

Step 2: Amination reaction, introducing the amino group into the ethyl carbazole molecule.

Chemical equation:

C₁₄H₁₃N+H₃N → C₁₄H₁₄N₂

In addition to the above methods, there is also another laboratory synthesis method for 3AE-C.

1. Preparation of raw materials:

-9-Ethylcarbazole: It can be obtained by reacting carbazole with ethyl bromide.

-Hydrazine hydrate or hydrazine monohydrate: used to introduce amino groups.

2. Synthesis steps of 3AE-C:

This synthesis method involves two main steps: alkylation reaction and amination reaction.

Step 1: Alkylation reaction, introducing ethyl groups into the carbazole molecule.

Chemical equation:

C₁₂H₉N+C₈H₈BrCl → C₁₄H₁₃N

Step 2: Amination reaction, introducing the amino group into the ethyl carbazole molecule.

Chemical equation:

C₁₄H₁₃N+Hydrazine hydrate → C₁₄H₁₄N₂+H₂O

The following are some of the main reaction properties of 3-Amino-9-ethylcarbazole:

1. Oxidation reaction:

3AE-C can be oxidized by oxidants to corresponding ketone derivatives. Commonly used oxidants include hydrogen peroxide (H₂O₂) and zinc oxychloride (ZnCl₂). The specific reaction equation is as follows:

(1) Oxidation reaction using hydrogen peroxide:

C1₄H₁₄N₂+H₂O₂ → C₁₄H₁₃N+NH₃+H₂O

(2) Using zinc oxychloride for oxidation reaction:

C₁₄H₁₄N₂+ZnCl₂ → C₁₄H₁₃N+NH₄Cl

2. Reactive substitution reaction:

The amino groups and hydrogen atoms at the aromatic ring positions in 3AE-C can be functionalized through substitution reactions. For example, it can react with aldehydes or ketones to generate corresponding imines or amines:

(1) Reactions with aldehydes:

C₁₄H₁₄N₂+RCHO → RCH=N-C₉H₈NH₂+H₂O

(2) Reactions with ketones:

C₁₄H₁₄N₂+R₂CO → R2C=N-C₉H₈NH₂+H₂O

3. Acid-base neutralization reaction:

3AE-C is an alkaline compound that can undergo neutralization reactions with acids. Common neutralization reactions include reactions with inorganic acids (such as hydrochloric acid) or organic acids (such as acetic acid). The specific reaction equation is as follows:

(1) Reaction with hydrochloric acid:

C₁₄H₁₄N₂+HCl → C₉H₈NH₃Cl

(2) Reaction with acetic acid:

C₁₄H₁₄N₂+CH₃COOH → C₉H₈NH₂CH₃COOH

4. Cycloaddition reaction:

The imine portion in 3AE-C can participate in cycloaddition reactions, generating nitrogen-containing ring compounds. For example, it can be associated with α,β- Unsaturated carbonyl compounds react to produce 1,2,3,4-tetrahydrogen [1] benzo [4,5] imidazoline:

C14H14N2+ α,β- Unsaturated carbonyl compounds → 1,2,3,4-tetrahydrogen [1] benzo [4,5] imidazoline

3-Amino-9-ethylcarbazole is an organic compound with a specific chemical structure, which has certain applications in chemical synthesis, materials science, and biomedical research. However, like many chemicals, it may also have potential adverse effects on human health and the environment while exerting its application value.

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