(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.) |
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Density |
0.962 g/mL at 20℃(lit.) |
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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.
(Trifluoromethyl)trimethylsilane 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.
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.
In the synthesis process of the core fluorine-containing acid sensitive monomer in 193nm ArF immersion photoresist, TMSCF3 is the only reagent that can accurately introduce trifluoromethyl tertiary alcohol structure on an industrial scale. Introducing trifluoromethyl tertiary alcohol groups into the resin structure of photoresist can significantly improve its 193nm transmittance and enhance its resistance to dry etching. The resolution of photoresist can be increased to below 7nm, fully meeting the lithography requirements of advanced process chips.
The traditional synthesis process of this type of fluorinated monomer requires the use of the extremely dangerous precursor gas trifluoromethyl bromide of trifluoromethyltrimethylsilane, and the reaction needs to be carried out at ultra-low temperatures of -78 ℃, which is completely impossible to achieve large-scale industrial production.
However, the process using TMSCF3 as the trifluoromethylation reagent can complete the reaction at room temperature and pressure, and the purity of the product can reach 99.99% stably, with a total metal impurity content of less than 0.1ppm, fully meeting the quality requirements of semiconductor grade photoresist monomers. At present, the top domestic photoresist companies have completed mass production of the fluorinated monomer, breaking the long-term monopoly of overseas companies in the ArF photoresist field.
Fluorinated functional components of next-generation EUV photoresist
In the development of the next generation extreme ultraviolet (EUV) photoresist, TMSCF3 is used to synthesize highly absorbing fluorine-containing photoacid generators. Introducing multiple trifluoromethyl groups into the molecular structure of the photo acid generator can significantly enhance its EUV photon absorption cross section and significantly increase the intensity of the generated acid.
The exposure sensitivity of EUV photoresist has been increased by more than twice, completely solving the long-standing limitation of exposure speed in EUV lithography machine production capacity. At present, multiple domestic research institutions and enterprises are developing EUV photoresist with independent intellectual property rights based on TMSCF3, and the related technology has entered the pilot stage.
Fluorinated Electronic Precursors for Semiconductor Chip Manufacturing
TMSCF3 can be further fluorinated and cracked to synthesize environmentally friendly fluorinated electronic specialty gases for the etching of next-generation semiconductor chips. The greenhouse effect potential (GWP) of this new etching gas is only 1% of that of traditional perfluorinated etching gases, while the etching selectivity for silicon-based media is increased by more than three times,
making it a core electronic specialty gas for the next generation of green semiconductor manufacturing. At present, this technology has completed pilot development in top domestic electronic and special gas enterprises, and will be applied in large-scale production in the future.
Trifluoromethyl carbonate additives for high-voltage electrolytes
A novel carbonate electrolyte solvent containing trifluoromethyl groups can be efficiently synthesized through the nucleophilic substitution reaction between TMSCF3 and dimethyl carbonate. The flash point of this new fluorinated solvent exceeds 130 ℃, and the electrochemical stability window reaches over 5.2V, fully suitable for high-voltage power battery systems above 4.6V. At the same time, a dense and stable CEI film can be formed on the positive electrode surface, significantly inhibiting the oxidation and decomposition of the electrolyte under high voltage.
In the testing of high nickel ternary power batteries, using the electrolyte containing fluorinated carbonate as the main solvent, the cycle life of the battery was increased from 1200 times to 2800 times, and the storage expansion rate of the battery at a high temperature of 60 ℃ was reduced by 70%. The comprehensive performance far exceeded that of traditional carbonate electrolyte systems. At present, several leading electrolyte companies in China have completed the pilot production of the fluorine-containing solvent and begun mass application in the new generation of long-range power batteries.
Core trifluoromethyl block of the new generation of fluorine-containing herbicides
The fluorine-containing chiral herbicide synthesized by TMSCF3 has a herbicidal activity more than 10 times that of traditional herbicides, with a dosage of only a few grams per mu of land, far lower than that of traditional pesticides. At the same time, this pesticide can be rapidly and completely degraded in the natural environment, almost without producing pesticide residues, making it a core variety for promoting green agriculture.
The fluorinated insect growth regulator synthesized using TMSCF3 can specifically interfere with the molting process of pests, and is completely non-toxic to natural enemies and mammals of pests, making it a new generation of environmentally friendly insecticides. The field efficacy of this insecticide exceeds 95%, and it does not cause pest resistance. It has been widely applied in multiple green organic agricultural bases in China.
Frequently Asked Questions
What is trifluoromethyl?
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The trifluoromethyl group is defined as a -CF3 substituent that, when introduced into an organic compound, can significantly alter its physical, chemical, and biological properties, often increasing its lipophilicity. AI generated definition based on: Tetrahedron, 2000.
What is trimethylsilane used for?
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Trimethylsilane (Si(CH3)3H) is a volatile organosilicon compound used in semiconductor processing and chemical synthesis. It serves as a precursor for silicon-containing films and surface treatments, offering controlled reactivity and deposition characteristics.
What drugs have a trifluoromethyl group?
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Some notable drugs containing trifluoromethyl groups include efavirenz (Sustiva), an HIV reverse transcriptase inhibitor; fluoxetine (Prozac), an antidepressant; and celecoxib (Celebrex), a nonsteroidal anti-inflammatory drug. Similar to pharmaceuticals, many pesticides also contain one or more trifluoromethyl groups.
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