(Trifluoromethyl)trimethylsilane,The Chinese name is trifluoromethyltrimethylsilane, which is a chemical substance. The appearance is a transparent colorless solution, soluble in most organic solvents, sensitive to acids, bases, and moisture, and requires storage under dry conditions and use in a fume hood. It can be used as a valuable reagent for trifluoromethylation of electrophilic substrates and for nucleophilic addition reactions of aldehydes and ketones. It reacts with catalytic F - (or CsF) to form trifluoromethyl and reacts with carbonyl compounds to form trifluoromethyl alcohols. Can be used as biomaterials or organic compounds for life science related research. Belonging to flammable liquid (category 2), it is necessary to keep away from heat sources, sparks, open flames, and hot surfaces during use, prohibit smoking, and keep the container sealed.
Additional information of chemical compound:
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Chemical Formula |
C4H9F3Si |
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Exact Mass |
142.04 |
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Molecular Weight |
142.20 |
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m/z |
142.04(100.0%),143.04(5.1%),143.05(4.3%),144.04(3.3%) |
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Elemental Analysis |
C, 33.79; H, 6.38; F, 40.08; Si, 19.75 |
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Boiling point |
54-55℃(lit.) |
|
Density |
0.962 g/mL at 20℃(lit.) |
|
Storage conditions |
2-8℃ |
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Chemical Structure
● Molecular Architecture
TMSCF₃ has the molecular formula C₄H₉F₃Si, with a molar mass of 142.20 g/mol. Its structure consists of a central silicon atom bonded to three methyl groups (–CH₃) and a trifluoromethyl group (–CF₃). The trifluoromethyl group is highly electron-withdrawing due to the electronegativity of fluorine, creating a strong inductive effect that stabilizes adjacent negative charges and polarizes bonds in nucleophilic addition reactions. The TMS group, conversely, acts as a leaving group, facilitating the transfer of the –CF₃ moiety to substrates.
● Physical and Chemical Properties
Appearance: Colorless liquid.
Density: 0.926–0.962 g/cm³ (at 20 °C).
Flammability: Highly flammable (flash point: –17 °C).
Reactivity: Reacts violently with water, releasing flammable gases (e.g., silanes and HF), necessitating anhydrous handling under inert gas (e.g., nitrogen or argon).
Stability: Volatile and moisture-sensitive; decomposes upon prolonged exposure to air or light.
These properties underscore the need for rigorous safety protocols, including storage in sealed containers away from heat and moisture, and the use of personal protective equipment (PPE) during handling.
(Trifluoromethyl)trimethylsilane is an important organic synthesis reagent with a wide range of applications. The following is a detailed explanation of its purpose:
Trifluoromethyltrimethylsilane (TFMS) is an efficient trifluoromethylation reagent that plays an important role in organic synthesis. It can introduce trifluoromethyl into the target molecule through nucleophilic addition reactions with compounds such as aldehydes and ketones. This reaction condition is mild, easy to operate, and the product is easy to separate and purify. In drug synthesis, the introduction of trifluoromethyl can alter the biological activity, metabolic stability, and pharmacokinetic properties of drugs. TFMS, as a trifluoromethylation reagent, can conveniently introduce trifluoromethyl to synthesize drug molecules with novel biological activities. For example, some anti-tumor drugs, antiviral drugs, and neuroprotective drugs can improve their efficacy and reduce side effects by introducing trifluoromethyl. In the field of materials science, the introduction of trifluoromethyl can improve the properties of materials, such as increasing heat resistance, corrosion resistance, oxidation resistance, etc. TFMS, as a trifluoromethylation reagent, can be used to synthesize polymer materials with special properties, organic-inorganic composite materials, etc. These materials have broad application prospects in fields such as aerospace, electronic information, and new energy.
As a raw material for synthesizing other compounds
Synthesis of potassium (trifluoromethyl) - trimethoxyborate: Potassium (trifluoromethyl) - trimethoxyborate is an important organic boron compound with wide application value. This compound can be synthesized by reacting TFMS with potassium compounds and trimethoxyboronic acid. This compound has potential applications in catalytic reactions, material synthesis, and other fields.
Synthesis of trifluoromethyl copper compounds: trifluoromethyl copper compounds are a class of compounds with special structures and properties that play important roles in organic synthesis and catalytic reactions. By reacting TFMS with copper compounds, trifluoromethyl copper compounds with different structures and functions can be synthesized. These compounds have wide application value in catalytic reactions, drug synthesis, and other fields.
Synthesis of other fluorine-containing compounds: In addition to the above compounds, TFMS can also be used to synthesize other fluorine-containing compounds, such as trifluoromethanesulfonamide with trifluoromethylthiolation, difluoromethyl trifluoromethanesulfonate, etc. These compounds have broad application prospects in fields such as organic synthesis and medicinal chemistry.
Trifluoromethyltrimethylsilane can also serve as a catalyst and promoter, promoting reaction progress, increasing reaction rate, and selectivity in chemical reactions.
Catalyst: TFMS can serve as a catalyst for certain chemical reactions, such as esterification and alkylation reactions. By introducing trifluoromethyl, the activity and selectivity of reactants can be altered, thereby improving reaction efficiency and product purity.
Additives: TFMS can be used as additives in certain chemical reactions, such as solvents, stabilizers, etc. It can form stable complexes or coordination compounds with other compounds, thereby improving reaction conditions and enhancing reaction efficiency.
other purposes
Used for preparing ion exchange resins: TFMS can be used with other compounds to prepare resins with specific ion exchange properties through cross-linking reactions. These resins have broad application prospects in fields such as water treatment and wastewater treatment.
Used for preparing surfactants: TFMS can serve as a precursor compound for surfactants, synthesizing compounds with specific surface activity by reacting with other compounds. These compounds have a wide range of application value in daily chemical products, oilfield chemicals, and other fields.
Used for preparing gas purifiers: TFMS can also be used to prepare gas purifiers by reacting with impurities in the gas to convert them into harmless or easily manageable substances. This gas purifier has potential application prospects in the field of environmental protection.
What are the side effects of this compound?
1.Chemical properties and potential risks
Flammability and explosiveness
(Trifluoromethyl)trimethylsilane is a flammable and explosive compound, which means that improper handling during storage, transportation, and use may lead to fire or explosion accidents.
Therefore, when using TFMS, it is necessary to strictly follow safety operating procedures, ensure good ventilation in the workplace, and stay away from fire and heat sources.
Toxicity
Although the specific toxicity data of TFMS may vary depending on experimental conditions and testing methods, as a fluorinated organic compound, it may have certain toxic effects on the human body.
Toxicity may manifest as irritation to the skin, eyes, and respiratory tract, as well as chronic health problems that may arise from long-term exposure.
2.Potential impact on human health
Skin contact
TFMS may undergo chemical reactions with the skin, leading to redness, swelling, pain, burns, etc. Long term exposure may lead to health problems such as skin inflammation and allergies.
Eye contact
TFMS may cause strong irritation to the eyes, leading to eye pain, tearing, redness, and swelling. In severe cases, it may lead to blindness in the eyes.
Inhalation
Long term inhalation of TFMS vapors may cause irritation to the respiratory tract, leading to symptoms such as coughing and difficulty breathing. Long term inhalation may lead to respiratory diseases such as bronchitis, asthma, etc.
Ingestion
If TFMS is ingested by mistake, it may cause corrosion and burns to the oral, esophageal, and gastric mucosa. There may be digestive system symptoms such as nausea, vomiting, and abdominal pain. In severe cases, it may lead to toxic shock or death.
3. Environmental and Health Risks
Environmental pollution
(Trifluoromethyl)trimethylsilane may generate pollutants such as wastewater, exhaust gas, and solid waste during production and use. If these pollutants are not properly treated, they may cause pollution to the environment, affecting ecosystems and human health.
Long term exposure risk
Long term exposure to TFMS may lead to chronic health problems such as neurological damage, liver and kidney damage, etc. These health issues may only appear after years of exposure to TFMS, and therefore should be given sufficient attention.
4.Suggestions for safe use
Personal protection
When using TFMS, appropriate personal protective equipment should be worn, such as protective gloves, goggles, masks, and protective clothing. Ensure good ventilation in the workplace and avoid prolonged inhalation of TFMS vapors.
Storage and transportation
Store TFMS in a cool, well ventilated place, away from sources of fire and heat. During transportation, it is necessary to ensure that the packaging of TFMS is intact and in compliance with relevant transportation regulations.
Waste disposal
Abandoned TFMS and its packaging should be properly disposed of in accordance with relevant regulations to avoid environmental pollution.
Training and Awareness
Provide safety training to personnel using TFMS to enhance their safety awareness and operational skills.
Ensure that all personnel are aware of the potential risks and response measures of TFMS.
Future Prospects
The demand for TMSCF₃ is projected to grow at a CAGR of 6.2% through 2030, driven by:
1)Green Chemistry: Development of safer, more sustainable synthesis routes (e.g., electrochemical fluorination).
2)Bioconjugation: Exploring TMSCF₃ in site-specific protein modification for targeted therapeutics.
3)3D Printing: Incorporating fluorinated polymers into additive manufacturing to create high-performance materials.
Additionally, advances in flow chemistry and machine learning-guided reaction optimization promise to enhance TMSCF₃'s utility in complex syntheses.
Trifluoromethyltrimethylsilane (TMSCF₃) exemplifies the synergy between chemical innovation and industrial application. From its humble beginnings as a laboratory reagent to its pivotal role in drug discovery, materials engineering, and analytical science, TMSCF₃ has redefined the boundaries of fluorine chemistry. As researchers continue to unlock its potential, this versatile compound will undoubtedly remain at the forefront of scientific and technological progress, shaping the future of medicine, energy, and sustainability.
By understanding TMSCF₃'s properties, synthesis, and applications, chemists and engineers can harness its power to address some of the most pressing challenges of our time-proving that even the smallest molecules can drive monumental change.
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