1-bromodibenzothiophene, molecular formula C12H7BrS, CAS 65642-94-6, its appearance is a white to orange to green powder or crystal. It has better solubility in organic solvents, but poorer solubility in water. This property has significant implications for its applications in organic synthesis, material preparation, and analytical testing.For example, in pesticide synthesis, it can serve as an intermediate for synthesizing pesticide molecules with specific insecticidal or herbicidal activity;
|
|
|
|
Chemical Formula |
C12H7BrS |
|
Exact Mass |
262 |
|
Molecular Weight |
263 |
|
m/z |
262 (100.0%), 264 (97.3%), 263 (13.0%), 265 (12.6%), 264 (4.5%), 266 (4.4%) |
|
Elemental Analysis |
C, 54.77; H, 2.68; Br, 30.36; S, 12.18 |
Optoelectronic materials
This substance and its derivatives have potential application value in the field of optoelectronic materials. Due to the conjugated nature of thiophene rings, these compounds can absorb and emit light of specific wavelengths, making them suitable as active materials for optoelectronic devices such as organic solar cells and organic light-emitting diodes (OLEDs). In addition, by regulating the molecular structure and composition of compounds.
Semiconductor materials
Some derivatives of this substance have semiconductor properties and can be used as semiconductor materials. These materials have broad application prospects in fields such as electronic devices and sensors. For example, they can be used as channel materials for field-effect transistors or for the fabrication of sensors with specific functions.
Catalyst carrier
In catalytic reactions, this substance and its derivatives can also serve as carriers for catalysts. By fixing the catalyst on a carrier, the stability and recyclability of the catalyst can be improved, thereby reducing production costs and minimizing environmental pollution. In addition, the functional groups on the carrier can also have a synergistic effect with the catalyst, further improving the catalytic efficiency.
The synthesis of 1-Bromodibenzothiophene is an important organic synthesis work, and this compound has a wide range of applications in the fields of medicine and materials science. The following is a common laboratory synthesis method, including detailed steps and corresponding chemical equations:
Materials and Instruments
1. Raw materials:
-2,3-Dibromothiophene
-Diphenyl sulfide
-Solvent: such as acetonitrile, dimethyl sulfoxide (DMSO), etc
2. Reagents:
-Sodium hydroxide (NaOH)
-Bromine (Br2)
-Copper iodide (CuI)
-Dimethyl sulfoxide (DMSO)
3. Instruments:
-Reflux device
-Reaction vessel under inert atmosphere (such as nitrogen) protection
-Magnetic stirrer
Synthesis steps
Preparation of 2,3-dibromothiophene:
2,3-dibromothiophene is a precursor of 1-bromo-2,3-dibenzothiophene, which can be synthesized through the following reaction:
Reaction equation:
2,3-dibromothiophene+bromine → → CuI, DMSO 1-bromo-2,3-dibromothiophene
In the solvent DMSO, 2,3-dibromothiophene reacts with bromine to produce 1-bromo-2,3-dibromothiophene.
Preparation of 1-bromo-2,3-dibenzothiophene:
Now, we will convert 1-bromo-2,3-dibromothiophene into the target product 1-bromo-2,3-dibenzothiophene. The reaction is as follows:
Reaction equation:
1-bromo-2,3-dibromothiophene + C12H10S +NaOH →1-bromo-2,3-dibenzothiophene+NaBr+ C8H6
Under alkaline conditions (using NaOH), 1-bromo-2,3-dibromothiophene reacts with diphenyl sulfide to produce 1-bromo-2,3-dibenzothiophene and benzothiophene as by-products. This reaction is usually carried out under an inert atmosphere to prevent oxidation or other side reactions from occurring.
Reaction mechanism
Reaction mechanism for preparing 2,3-dibromothiophene:
In DMSO solvent, CuI acts as a catalyst to promote the reaction between bromine and 2,3-dibromothiophene. The initial steps of the reaction may involve the generation of bromide ions from CuI, which in turn triggers a bromine substitution reaction in the 2,3-dibromothiophene molecule. This catalytic effect helps accelerate the bromination reaction.
Reaction mechanism for preparing 1-bromo-2,3-dibenzothiophene:
The mechanism of the reaction between 1-bromo-2,3-dibromothiophene and diphenyl sulfide in the presence of NaOH involves nucleophilic substitution reaction under alkaline conditions. NaOH provides an alkaline environment, which promotes the departure of bromide ions in 1-bromo-2,3-dibromothiophene, forming an intermediate carbocation. This carbocation reacts with diphenyl sulfide via the SNAr reaction (nucleophilic aromatic substitution).
Fine Chemical Synthesis
1-bromodibenzothiophene is also used in the synthesis of various fine chemicals, such as dyes, pigments, and fragrances. The unique electronic properties of the compound can influence the color and optical properties of dyes and pigments, making them suitable for applications in the textile, printing, and coating industries. For example, 1-bromodibenzothiophene-based dyes have been synthesized with excellent color stability and high color strength, meeting the demanding requirements of modern dyeing processes.
1-bromodibenzothiophene can be used as a building block in the synthesis of fragrance compounds. By introducing different functional groups through chemical reactions, researchers can create a wide range of fragrance molecules with unique scents. These fragrance compounds find applications in the perfume, cosmetics, and personal care industries, enhancing the sensory experience of consumers.
1-Bromodibenzothiophene has a unique value as a probe molecule in the field of bioscience research. It can interact with certain structures or molecules in living organisms through specific chemical properties, thus revealing specific biological processes or signaling pathways in living organisms.
Design and selection of probe molecules
Structural properties:
the molecular structure of it contains bromine atoms and thiophene rings, and these structural properties enable it to specifically bind to certain receptors or enzymes in organisms.
Target selection:
a specific biological process or signaling pathway is selected as the object of study based on the purpose of the research. For example, processes can be focused on.
Synthesis and labeling:
Prepare 1-bromodibenzothiophene by chemical synthesis method and label it by appropriate labeling techniques for tracing and detecting in the organism.
Application of probe molecules
Intra-biological binding:
Introduce the labeled it into the organism, and reveal the distribution and function of these molecules through its specific binding to target molecules (e.g., receptors, enzymes, etc.).
Real-time monitoring:
Using advanced imaging technologies (e.g., fluorescence imaging, magnetic resonance imaging, etc.), the dynamic changes of 1-bromodibenzothiophene in the organism are monitored in real time, so as to understand the real-time status of the target biological processes or signaling pathways.
Data analysis:
By systematically collecting and professionally analyzing a full set of accurate biological imaging data, researchers are able to acquire comprehensive and detailed characteristic information concerning specific target biological processes and intracellular signaling pathways. This covers the exact occurrence time, spatial distribution position, dynamic reaction rate as well as the actual interaction relationship between the studied substance and other related biomolecules, laying solid data support for further mechanism research.
Example Applications&As antipsychotic drugs
Taking neuroscience research as an example, it can be used as a probe molecule to study the process of neurotransmitter release and transmission. By introducing it into the nervous system, its binding to specific neurotransmitter receptors can be observed, thus revealing the neurotransmitter's transmission pathway between neurons and the regulatory mechanism.Dibenzothiophene and its derivatives show great potential in the treatment of psychiatric disorders. They can improve a patient's psychiatric symptoms by modulating the levels of neurotransmitters.
Modulation of neurotransmitters:
dibenzothiophene can increase the levels of 5-hydroxytryptamine transporter, norepinephrine transporter, and dopamine transporter by blocking all three neurotransmitters. These neurotransmitters play an important role in regulating mood, stress resistance, etc. Therefore, dibenzothiophene is expected to be an effective drug for the treatment of mental illness.
Antipsychotic effects:
Clinical studies have shown that dibenzothiophene derivatives, such as quetiapine, have been approved for the treatment of schizophrenia. Quetiapine has affinity for 5-hydroxytryptamine receptor and dopamine D2 receptor, etc. It can bi-directionally regulate biphasic depression and mania, showing good therapeutic effect.
The potential applications of dibenzothiophene in neuroscience research are mainly in its ability to affect the function and mechanism of the nervous system as a drug or drug precursor, which may be used for the treatment of a variety of neurological disorders.
Treatment of psychiatric disorders
Dibenzothiophene can be used as an API for the preparation of other drugs which can be used for the treatment of mental disorders such as depression and anxiety. Dibenzothiophene can improve patients' depression and anxiety symptoms by regulating the levels of neurotransmitters, such as increasing the levels of neurotransmitters such as 5-hydroxytryptamine, norepinephrine and dopamine, to improve the stability of patients' moods and stress resistance. For example, quetiapine, a dibenzothiophene derivative, is approved as an atypical antipsychotic for the treatment of schizophrenia, and there are also studies suggesting that it may have potential for treating bipolar depression and mania
Other potential applications
In addition to the above applications, dibenzothiophene may have other potential applications in neuroscience. For example, it can be used as a research tool for exploring the functions and mechanisms of the nervous system, providing new ideas and methods for neuroscience research.
Treatment of cardiovascular diseases
Dibenzothiophene can also act as an anti-epileptic and alleviate the symptoms of Parkinson's disease by regulating the levels of neurotransmitters. Although its application in the treatment of neurological diseases needs further research, it has shown great application prospects.
Anti-cancer potential
In addition, dibenzothiophene has anti-cancer potential. It can have great application potential in the treatment of cancer by activating the autophagy of tumor cells, promoting the apoptosis of tumor cells and inhibiting the proliferation of tumor cells.
Although the application of this drug in cancer treatment is still in the preliminary stage, its effectiveness and safety have been preliminarily confirmed.
Treatment of neurological disorders
Dibenzothiophene can also act as an anti-epileptic and alleviate the symptoms of Parkinson's disease by regulating the levels of neurotransmitters.
Although its application in the treatment of neurological diseases needs further research, it has shown great application prospects.
In summary, dibenzothiophene has a wide range of potential applications in neuroscience research. It can be used in a variety of fields such as the treatment of psychiatric disorders, neurological disorders, cardiovascular diseases and cancer, providing new options and possibilities for neuroscience research and clinical treatment. However, these applications require further research and validation to ensure their safety and efficacy.
Frequently Asked Questions
What is the formula for dibenzothiophene?
+
-
C12H8S
Dibenzothiophene (DBT, diphenylene sulfide) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It has the chemical formula C12H8S.
What does the appearance look like?
+
-
White to orange to green powder or crystals.
Melting point?
+
-
Approximately 84°C.
How to Storage?
+
-
Store at room temperature. Avoid contact with strong oxidizing agents, strong acids, or strong alkalis to prevent hazardous reactions.
Can 1-bromodibenzothiophene be used for the synthesis of other complex organic molecules?
+
-
Yes, 1-bromodibenzothiophene, as a brominated aromatic compound, exhibits high reactivity. It can participate in substitution reactions, coupling reactions, and other processes via its bromine atom, enabling the synthesis of more complex organic molecules.
Hot Tags: 1-bromodibenzothiophene cas 65642-94-6, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 3 Nitrobenzonitrile, 8 Anilino 1 naphthalenesulfonic Acid CAS 82 76 8, Benzotriazole 1 yl oxytripyrrolidinophosphonium Hexafluorophosphate CAS 128625 52 5, Methylamine hydrochloride powder, 4 Hydroxyphenylacetic Acid CAS 156 38 7, 2,6-Pyridinedicarboxylic acid