Mesityl Iodide, also known as 2-iodo-1,3,5-trimethylbenzene, 2-iodo-1,3,5-trimethylbenzene Iodo-2,4,6-trimethylbenzene, Molecular formula C9H11I, CAS 4028-63-1. This compound is relatively stable at room temperature and pressure, and is not prone to decomposition or polymerization reactions. Almost insoluble in water at room temperature, but soluble in organic solvents such as ether, acetone, etc. Mainly used as an important intermediate in organic synthesis reactions. It is commonly used as an iodinated reagent for aromatic compounds, to introduce iodine atoms into the molecular structure, thereby altering its properties and reactivity. In addition, the compound can also serve as a component of certain luminescent materials.
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Chemical Formula |
C9H11I |
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Exact Mass |
246 |
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Molecular Weight |
246 |
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m/z |
246 (100.0%), 247 (9.7%) |
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Elemental Analysis |
C, 43.93; H, 4.51; I, 51.57 |
in chemical synthesis
As a Reactant in Aryl Substitution Reactions
Mesityl iodide can serve as a substrate in aryl substitution reactions, where the iodine atom can be replaced by other functional groups. This reactivity is leveraged in the synthesis of more complex organic molecules. For instance, through nucleophilic substitution reactions, which can be converted into derivatives with different functionalities, such as alcohols, amines, or esters, depending on the nucleophile used.
In Cross-Coupling Reactions
Cross-coupling reactions, such as the Suzuki-Miyaura coupling, are powerful tools in organic synthesis for forming carbon-carbon bonds. It can participate in these reactions, allowing for the incorporation of aryl groups into target molecules. This is particularly useful in the synthesis of pharmaceuticals, materials science, and other fields where aromatic compounds play crucial roles.
As a Source of Iodine for Labeling and Tracing
The iodine atom in TMI can be used as a tracer or label in chemical reactions. By incorporating TMI into a synthetic pathway, researchers can track the progress of reactions and the fate of specific intermediates or products. This is particularly useful in studying reaction mechanisms and optimizing synthetic routes.
in material science
TMI could serve as a precursor in the synthesis of various materials due to its aromatic and iodinated nature. Iodine-containing compounds often play crucial roles in the preparation of specific materials with desired electronic, optical, or catalytic properties.
In the field of polymer composites, it might be utilized as a modifier to alter the physical or chemical properties of polymers. The introduction of iodine atoms can influence the electrical conductivity, thermal stability, or flame retardancy of polymers.
Although not commonly discussed, the unique properties might make it useful in some aspects of semiconductor material processing. Iodine-containing compounds are known to participate in certain etching or doping processes in semiconductor manufacturing. However, specific applications in this area require further research and verification.
In material synthesis reactions, it could potentially act as a catalyst or reaction mediator. Its iodine atom might facilitate specific chemical transformations by participating in bond formation or cleavage processes.
Due to the presence of iodine, it might be of interest in the development of radiation-sensitive materials. These materials are often used in lithography or other microfabrication techniques where they undergo chemical changes upon exposure to radiation.
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in Analytical Chemistry
Mesityl iodide can serve as a versatile reagent in various chemical reactions due to its stable iodine substituent and the electron-donating effect of the methyl groups. It can participate in substitution reactions, addition reactions, and other types of organic transformations, making it a valuable tool for synthesizing complex molecules or modifying chemical structures in the laboratory.
In chromatographic analysis, TMI can be employed as a stationary phase modifier or a mobile phase additive to enhance the separation efficiency and selectivity of analytes. Its unique chemical properties can interact with analytes in specific ways, leading to improved resolution and peak shape in chromatographic separations.
Due to its distinctive spectroscopic properties, it can be used as an internal standard or a reference compound in spectroscopic analyses such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). By comparing the signals with those of the analytes of interest, researchers can accurately quantify the analytes present in a sample.
In kinetic studies of chemical reactions, it can be used as a tracer to monitor the progress of reactions and to investigate reaction mechanisms. By labeling specific reactants or intermediates with TMI, researchers can track their transformation over time and gain insights into the reaction pathways and rate-determining steps.
Given its iodine substituent, it has potential applications in radiochemical synthesis. By incorporating radioactive isotopes of iodine (such as I-125 or I-131) into the TMI structure, researchers can create radiolabeled compounds for use in imaging studies, tracer experiments, or therapeutic applications.
in organic chemistry
As an Intermediate in Organic Transformations
Reduction to Alcohols: TMI can be reduced to the corresponding alcohol using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4). This transformation provides a route to synthesizing aromatic alcohols, which are important intermediates in the synthesis of pharmaceuticals, fragrances, and other organic compounds.
Oxidation to Carboxylic Acids: Under appropriate conditions, it can be oxidized to the corresponding carboxylic acid. This reaction is valuable for introducing acidic functionalities into aromatic systems, which can be further derivatized in various ways.
As a Starting Material for the Preparation of Other Organic Compounds
Grignard Reactions: It can be used to prepare Grignard reagents (RMgX) by reacting with magnesium metal in the presence of an ether solvent. These Grignard reagents are highly reactive and can be used to synthesize a wide range of organic compounds, including alcohols, esters, and ketones.
Preparation of Aryl Halides: By reacting it with other halogens or halogenating agents, aryl halides with different halogen substituents can be obtained. These aryl halides are versatile intermediates in organic synthesis, capable of participating in numerous reactions such as nucleophilic substitution, elimination, and addition reactions.
At the nanoscale, iodine exhibits remarkable versatility by being encapsulated within diverse matrices, encompassing polymers, inorganic hosts, and intricate self-assembled structures. This encapsulation process results in the formation of a myriad of nanostructures, including nanoparticles, nanowires, and nanocapsules. The miniature dimensions of these iodine nanomaterials, which commonly span from a few nanometers to several hundred nanometers, play a pivotal role in elevating their surface-to-volume ratios. This characteristic enhancement significantly boosts their reactivity and interactions with their immediate surroundings, facilitating efficient energy transfer, catalytic activity, and enhanced optical properties. Such nanoscale manipulations not only harness the intrinsic properties of iodine but also amplify them for diverse technological applications, underscoring the transformative potential of iodine-based nanomaterials in the realm of nanotechnology.
Electronically, iodine nanomaterials distinguish themselves through their exceptional charge transport properties, positioning them as formidable contenders for incorporation into electronic devices, notably sensors and energy storage systems. These nanomaterials exhibit a remarkable capacity to store and release electrical charge with high efficiency, a trait that can be meticulously tailored by manipulating the size, shape, and chemical composition of the iodine-laden nanostructures. By fine-tuning these parameters, researchers can optimize the charge dynamics within the nanomaterials, enhancing their performance in energy conversion, storage, and sensing applications. This adaptability underscores the potential of iodine nanomaterials to revolutionize the functionality and efficiency of electronic devices, paving the way for advancements in sustainable energy technologies and sensitive detection systems.
Optically, iodine nanomaterials exhibit striking absorption and emission characteristics, particularly within the visible and near-infrared spectral regions. This optical prowess renders them highly appealing for photonics applications, including light-emitting diodes (LEDs), luminescent markers, and optical sensors. Their luminescent properties can be finely tuned and even augmented through strategic doping with other elements or via surface modifications. These adjustments allow for the precise manipulation of the nanomaterials' optical signatures, enabling them to emit light of specific colors or intensities tailored for diverse applications. This versatility underscores the potential of iodine nanomaterials to revolutionize photonic technologies, fostering advancements in lighting, imaging, and sensing systems that harness the power of light in innovative and efficient ways.
Catalytically, iodine nanomaterials have emerged as potent accelerators in a multitude of chemical reactions, spanning from organic synthesis to environmental remediation. Their elevated surface area, coupled with their tailored reactivity, underpins their capacity to enhance catalyst performance, resulting in higher yields and greater selectivity in targeted chemical transformations. By optimizing the size, shape, and surface chemistry of these nanostructures, researchers can fine-tune their catalytic properties to meet the specific demands of diverse chemical processes. This adaptability underscores the potential of iodine nanomaterials to revolutionize catalytic technologies, fostering advancements in the efficient and sustainable production of chemicals, as well as in addressing environmental challenges through innovative remediation strategies.
adverse reaction
Mesityl Iodide (chemical name: 2-iodo-1,3,5-trimethylbenzene, CAS number: 4028-63-1) is an aromatic compound containing iodine, with a molecular formula of C ₉ H ₁ I and a molecular weight of 246.09 g/mol. Its structure consists of three methyl groups replacing positions 1, 3, and 5 on the benzene ring, and an iodine atom connecting position 2. As an organic iodide, Mesityl Iodide is commonly used as an iodide reagent or intermediate in organic synthesis, participating in carbon carbon bond formation, cross coupling reactions, etc.
Acute toxic reaction
Local stimulation effect
Skin:
Direct contact with Mesityl Iodide may cause mild to moderate irritant reactions, manifested as redness, itching, or burning sensation. Similar compounds (such as methyl iodide) can cause the formation of skin blisters, indicating the need to be alert to delayed allergic reactions.
Eyes:
Dust or solution in contact with the eyes may cause conjunctivitis, manifested as congestion, tearing, or pain. Animal experiments have shown that iodides are corrosive to the cornea and require immediate flushing and medical attention.
Respiratory tract:
Inhaling dust or vapor may irritate the upper respiratory tract, causing coughing, sore throat, or shortness of breath. High concentration exposure may lead to chemical pneumonitis or pulmonary edema (refer to acute inhalation toxicity data of methyl iodide).
Systemic toxicity
Acute exposure may suppress the central nervous system (CNS), manifested as headaches, dizziness, drowsiness, or confusion. Similar compounds (such as methyl iodide) can cause cerebellar lesions, manifested as ataxia, tremor, or speech disorders, and in severe cases, coma or epileptic seizures. Oral or inhaled high doses may cause nausea, vomiting, abdominal pain, or diarrhea. Gastrointestinal bleeding has been reported in cases of methyl iodide poisoning, and caution should be exercised regarding the mucosal damaging effects of Mesityl Iodide.
Allergic reaction
Iodides may cause allergic reactions, manifested as rash, urticaria, or asthma attacks.
Repeated exposure may increase the risk of sensitization, and attention should be paid to the allergy history of occupational populations.
Chronic toxic reactions
Long term exposure to health effects
Neurological system: Chronic exposure may lead to changes in neurobehavior, such as memory loss, lack of concentration, or emotional fluctuations. Delayed onset mental disorders have been reported in cases of methyl iodide poisoning, suggesting the need for long-term follow-up of occupational exposure populations.
Thyroid: Iodides may interfere with thyroid function, leading to thyroid enlargement or hypothyroidism (especially in iodine sensitive individuals). Animal experiments have shown that long-term intake of iodide can cause thyroid follicular cell proliferation, and thyroid hormone levels need to be monitored.
Liver: Chronic exposure may lead to liver cell damage, manifested as elevated transaminase levels or jaundice.
Exposure route
Inhalation: Dust or vapor can enter the human body through the respiratory tract, especially in enclosed spaces or high-temperature operations where the risk increases.
Skin contact: Solid particles or solutions may come into direct contact with the skin, causing local irritation or absorption.
Eye contact: Dust or splashes may cause eye irritation.
Ingestion: Although not common, solid particles may be ingested through the hand mouth route.
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