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Trifluoromethanesulfonic acid

Trifluoromethanesulfonic Acid is a strong organic sulfonic acid with the chemical formula CF3SO3H.
It is a colorless, odorless liquid that is miscible with water and many organic solvents.
Trifluoromethanesulfonic Acid is a highly reactive and versatile compound used in a variety of chemical reactions, including as a catalyst, dehydrating agent, and electrophilic reagent.
It finds applications in organic synthesis, polymer chemistry, and materials science.
Researchers can use PubCompare.ai's AI-driven optimization tools to easily locate protocols from literature, preprints, and patents, and identify the best procedures and products to ensure reproducible and accurate research for their work with Trifluoromethanesulfonic Acid.

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Publication 2009
The synthesis of poly-D,L-lactide (PDLLA), and PCL was carried out in bulk by ring-opening polymerization (ROP) of the corresponding monomers (D,L-lactide, and ε-caprolactone). The reaction conditions were optimized to obtain polymers with similar molecular weight characteristics and intrinsic viscosities. Polymerization was carried out at 130 °C for 4 h under vacuum for PDLLA and for 21 h under argon atmosphere for PCL. The monomer to tin (II) octoate molar ratio in the case of PDLLA synthesis was 2500. PCL was synthesized by adding methanol as a co-initiator to the reaction system, and the ratio of [monomer]:[Sn(Oct)2]:[MeOH] was 5000:1:2. The resulting polymers were dissolved in a minimum amount of chloroform, precipitated into methanol, filtered, washed 2 times with methanol, and dried in vacuum at ~150 Pa. PDLLA and PCL yields were 83 and 57%, respectively.
Poly(L-lysine) (PLys) and random poly(amino acids), e.g., poly((L-lysine)-co-(L-leucine)) (P(Lys-co-Leu)) and poly((L-lysine)-co-(L-phenylalanine)) (P(Lys-co-Phe)), used to modify the surface of films based on aliphatic polyesters with amino groups were obtained at the Institute of Macromolecular Compounds RAS according to the previously developed protocol [39 (link),40 (link)]. The synthesis was carried out by ROP of pre-synthesized N-carboxyanhydrides (NCA) of the corresponding α-amino acids. n-Hexylamine was used as the initiator. The molar ratio of monomer to initiator was 50. The molar ratio between ε-benzyloxycarbonyl-L-lysine (Lys(Z)) NCA and the hydrophobic amino acid NCA was 4 in the case of L-leucine NCA and 8 in the case of L-phenylalanine NCA.
Weight average molecular weights (Mw) and dispersity (Ð) of all synthesized polymers were determined by size-exclusion chromatography (SEC) using a Shimadzu HPLC system (Tokyo, Japan) consisting of a pump LC-10AD VP, refractometric detector RID-10A, column oven CTO-20A, system controller SCL-10A VP (Canby, OR, USA) supplied with a Rheodyne 725i injection valve (Rohnert Park, CA, USA) and two Agilent PLgel MIXED-D columns (5 µм, 7.5 × 300 mm, Agilent Technologies, Santa-Clara, CA, USA). LC Solution Shimadzu software (version 1.25, Kyoto, Japan) was used to collect and process data.
Molecular weight characteristics of aliphatic polyesters were determined at a mobile phase flow rate of 1.0 mL/min and 40 °C using tetrahydrofuran as an eluent and polystyrene standards with molecular weights ranging from 2000 to 450,000 (Agilent Technologies, Santa Clara, CA, USA and Waters, Milford, MA, USA) for calibration. Mw and Ð for PDLLA and PCL were 137,000, 1.7, and 123,000 and 1.6, respectively. In the case of poly(amino acids), the analysis was carried out for protected (co)polymers using 0.1 M solution of lithium bromide in N,N-dimethylformamide as a mobile phase and poly(methyl methacrylate) standards with molecular weights ranging from 17,000 to 250,000 for calibration at a mobile phase flow rate of 0.7 mL/min and 40 °C. Their molecular weight characteristics were as follows: Mw = 38,500 and Ð = 1.1 for PLys(Z); Mw = 26,600 and Ð 1.3 for P(Lys(Z)-co-Leu); Mw = 36,300 and Ð = 1.4 for P(Lys(Z)-co-Phe). Deprotection of poly(amino acids) was carried out with the use of a 5.25% solution of trifluoromethanesulfonic acid in trifluoroacetic acid for 4 h. The complete deprotection was confirmed by 1H NMR spectroscopy (AVANCE AV-400 NMR spectrometer, Bruker, Karlsruhe, Germany) by the disappearance from the spectra of signals corresponding to the methylene group (5.0 ppm) and the aromatic fragment (7.1 ppm) of Z-protective groups (-O-CH2-C6H5).
The viscosity of a series of aliphatic polyesters solutions at various concentrations in chloroform was measured using an Ostwald’s capillary viscosimeter. Intrinsic viscosities calculated from the obtained data were 1.1 and 1.3 dL/g for PDLLA and PCL, respectively.
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Publication 2022
The N-(2-aminoethyl)glycine PNA (aegPNA) monomers were purchased from ASM Research Chemicals. PNA monomer J was synthesized following the reported method (35 (link),47 (link)). Synthesis of PNA oligomers was carried out on 4-methylbenzhydrylamine hydrochloride (MBHA∙HCl) polystyrene based resin. The original loading value 1.5–1.7 mmol/g of this solid support was reduced to 0.35 mmol/g, using acetic anhydride as the capping reagent. (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBop) and N,N-Diisopropylethylamine (DIPEA) were used as the coupling reagent and Boc strategy was followed during oligomer synthesis. After sequential deprotection of t-Boc group and coupling of aeg/modified PNA monomers on solid support, final cleavage of the oligomers were done by using ‘high-low trifluoroacetic acid (TFA)-trifluoromethanesulfonic acid (TFMSA)’ method. Oligomers were then precipitated with diethyl ether, dissolved in water and purified by RP-HPLC method using water-CH3CN-0.1% TFA as the mobile phase. Sample crystallization matrix α-cyano-4-hydroxycinnamic acid (CHCA) was used in matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) to characterize the oligomers.
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Publication 2014
acetic anhydride Anabolism Coumaric Acids Crystallization Cytokinesis Ethyl Ether Glycine High-Performance Liquid Chromatographies Polystyrenes Resins, Plant Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization t-butyloxycarbonyl group Trifluoroacetic Acid trifluoromethanesulfonic acid

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Publication 2009
Acetone Androgen-Insensitivity Syndrome Carbon Cells Centrifugation Hyphae Protein C Proteins Secretome Staphylococcal Protein A Sucrose Trichloroacetic Acid Yeast Proteins

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Publication 2009
Agar Androgen-Insensitivity Syndrome Buffers Cell Wall Centrifugation Cold Temperature Conidia COOL-1 protein, human Cytosol Filtration Freezing Hyphae Nitrogen Pellets, Drug Powder Proteins Solon Sterility, Reproductive Sucrose Trypsin

Most recents protocols related to «Trifluoromethanesulfonic acid»

Chemical deglycosylation of rLdpA was performed using trifluoromethanesulfonic acid (TFMS) (Sigma-Aldrich), as described previously [35 (link),36 (link)]. After treatment with TFMS, the shift in protein Mr was assessed by SDS-PAGE. Bovine fetuin (Sigma-Aldrich) and BSA (Sigma-Aldrich) were used as glycoprotein and non-glycoprotein controls, respectively.
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Publication 2024
The synthetic
process for PAP is illustrated in Scheme 1. In a flask equipped with an ice bath, 1.47
g of N-methyl-4-piperidone and 2.30 g of m-terphenyl were dissolved in 20 mL of DCM to form a mixture.
Next, 8.80 mL of trifluoromethanesulfonic acid was added to the above
mixture. The resulting brown solution turned viscous after 24 h, which
was then precipitated in water. The resulting PAP was washed with
water and dried at 60 °C.
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Publication 2024

Example 1

350 g of dry toluene was added to 1 liter flask equipped with a stir rod & a stir paddle, and heated to 45° C. over 10 min with stirring at 300 RPM under nitrogen flow. 10 g of anhydrous AlCl3 was added under stirring with the container rinsed with 50 g of toluene. After 10 minutes at 45° C., 250 g of 1,3-DIPEB was added over 30 min with reaction maintained at 45±2° C. The stirring rate was increased to 450 RPM, and final reaction mixture was very thick and became a gel. After being held at 45° C. for 1 hr, the reaction mixture was quenched with 150 mL of deionized H2O containing 4 grams of 85% H2SO4, and then heated up to 80° C. over 15 min. After 20 min at 80° C. under constant stirring, the reaction mixture allowed to phase separate over 15 min. The bottom aqueous layer was removed with a pipette. Stirring of the remaining top layer was resumed at 300 RPM, and 150 mL H2O having 4 grams of 85 wt % H2SO4 was added, and the mixture heated to 80° C., and stirred at 300 RPM for 20 min. The phases was allowed to separate with a bottom aqueous layer, which was removed using a pipette. A third wash of the top layer was made using 150 mL H2O with 4 grams of 85 wt % H2SO4 as described above. After removing the aqueous layer, the organic layer was quenched with 150 mL of H2O containing 0.8 g Na2CO3, and then heated to 80° C. for 20 min with stirring, the layers were allowed to settle for 10 min and the bottom aqueous layer was removed. The resulting organic layer was quenched with aqueous Na2CO3 using the same process as above. The organic layer was poured into 3 liters of chilled acetone under stirring to precipitate out the polymer product. The solids were filtered with a 110 mm Buchner funnel using a qualitative filter paper. 171.48 g of a wet mass was collected which after being dried in a constant vacuum oven at 0.1 mm Hg and 180° C. provided 133.2 g (53.3% yield) of the polymer.

The product was analyzed for iodine value (for degree of olefinic unsaturation present in the polymer), Tg, gel content, and molecular weight of THF-soluble material (using GPC). Results show an iodine value of 3.3 cg 1/g, a Mn of 3,087, a Mw of 44,926 for the THF-soluble material; a PDI of 14.6, a Tg of 185.2° C., and gel content of 60 wt. %.

Example 2

Example 1 was repeated, except that the amount of dry toluene is 1,068 g, the amount of 1,3-DIPEB is 125 g and 1.35 g of trifluoromethanesulfonic acid (triflic acid). The final dry mass from the reaction was 39.08 g for a yield of 33.75%. The final product had an iodine value of 2.4 cg 1/g, a Mn of 6,114, a Mw of 56,633 for the THF-soluble material; a PDI of 9.26, a Tg of 222.7° C., and gel content of 7.4 wt. %.

Example 3

Example 1 was repeated, except that the amount of dry cyclohexane is 389.3 g, the amount of 1,3-DIPEB is 105 g, and 0.7 g of trifluoromethanesulfonic acid (triflic acid). The wet mass (157.87 g) recovered from the Roto-vapor was placed in a vacuum oven at 180° C. under 0.1 mm Hg. After being dried for 2 h and 20 min, 103.56 g (98.63% yield) of the polymer was obtained as a dry mass.

The final product had an iodine value of 1.5 cg 1/g, a Mn of 2,433, a Mw of 24,285 for the THF-soluble material; a PDI of 9.98, a Tg of 215.8° C., and 2.8 wt. % gel content.

Example 4

Example 1 was repeated, except that the amount of dry cyclohexane is 928.4 g, the amount of 1,3-DIPEB is 250 g, and 0.25 g of trifluoromethanesulfonic acid (triflic acid). The dry mass recovered from the vacuum oven weighed 250.57 g (100.2%).

The final product had an iodine value of 5.5 cg 1/g, a Mn of 2,303, a Mw of 29.524 for the THF-soluble material; a PDI of 6.00, a Tg of 199.8° C., <0.01 wt. % gel content.

Example 5

Example 1 was repeated, except that the amount of dry cyclohexane is 927 g, the amount of 1,3-DIPEB is 250 g, and 0.25 g of trifluoromethanesulfonic acid (triflic acid). The wet mass recovered (322.97 g) was dried for 4 h in a vacuum oven at 180° C. under 0.1 mm Hg. The dry mass recovered from the vacuum oven weighed 238.38 g (95.4% yield).

The final product had an iodine value of 17.3 cg 1/g, a Mn of 1.989, a Mw of 26,099 for the THF-soluble material; PDI of 13.10, a Tg of 200.4° C., <0.01 wt. % gel content.

Example 6

Example 1 was repeated, that the amount of dry cyclohexane is 927 g, the amount of 1,3-DIPEB is 250 g, and 0.25 g of trifluoromethanesulfonic acid (triflic acid). The wet mass (245.7 g) remaining was dried in a vacuum oven set at 180° C. under 0.1 mm Hg for 4 h. The resulting dry mass weighed 249.6 g (99.8% yield).

The final product had an iodine value of 9.5 cg 1/g, a Mn of 1,660, a Mw of 14,080 for the THF-soluble material; a PDI of 8.47, a Tg of 200.0° C., <0.01 wt. % gel content.

Example 7

Example 1 was repeated, except that the that the amount of dry cyclohexane is 927 g, the amount of 1,3-DIPEB is 250 g, and the amount of trifluoromethanesulfonic acid (triflic acid) catalyst is 0.125 g.

The wet mass (245.7 g) remaining was dried in a vacuum oven set at 180° C. under 0.1 mm Hg for 4 h. The resulting dry mass weighed 249.6 g (99.8% yield).

The final product had an iodine value of 21.6 cg 1/g, a Mn of 2,953, a Mw of 80,167 for the THF-soluble material; a PDI of 27.15, a Tg of 195.9° C., <0.01 wt. % gel content.

Example 8

Example 1 was repeated, except that the amount of dry cyclohexane is 1179 g, the amount of 1,3-DIPEB is 250 g, and 0.125 g of triflic acid. In Example 8, catalyst added to heated mixture of 1,3-DIPEB and cyclohexane. The wet mass (245.7 g) remaining was dried in a vacuum oven set at 180° C. under 0.1 mm Hg for 4 h. The resulting dry mass weighed 249.6 g (99.8% yield).

The final product had an iodine value of 37.2 cg 1/g, a Mn of 2,161, a Mw of 58,088 for the THF-soluble material; a PDI of 26.89, a Tg of 67.3° C., <0.01 wt. % gel content.

Example 9

Example 1 was repeated, except that the amount of dry cyclohexane is 927 g, the amount of 1,3-DIPEB is 250 g, and 0.25 g of trifluoromethanesulfonic acid (triflic acid). The wet mass (245.7 g) remaining was dried in a vacuum oven set at 180° C. under 0.1 mm Hg for 4 h. The resulting dry mass weighed 249.6 g (99.8% yield).

The final product had an iodine value of 53.4 cg 1/g, a Mn of 1,107, a Mw of 4,792 for the THF-soluble material; a PDI of 4.33, a Tg of 66.02° C., <0.01 wt. % gel content.

Example 10

Example 1 was repeated, except that the amount of dry cyclohexane is 198 g, the amount 1,3-DIPEB is 42 g, and 0.25 g of trifluoromethanesulfonic acid (triflic acid). The wet mass (245.7 g) remaining was dried in a vacuum oven set at 180° C. under 0.1 mm Hg for 4 h. The resulting dry mass weighed 249.6 g (99.8% yield).

The final product had an iodine value of 10.9 cg 1/g, a Mn of 1,520, a Mw of 5,024 for the THF-soluble material; a PDI of 3.31, a Tg of 173.3° C., <0.01 wt. % gel content.

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Patent 2024
4‐Benzyl‐L‐aspartate, 4‐nitrophenyl chloroformate, dithiothreitol, trifluoromethanesulfonic acid, and trifluoroacetic acid were obtained from TCI (Eschborn, Germany). L‐phenylalanine was purchased from Carl Roth (Karlsruhe, Germany). S‐carbobenzoxy‐L‐cysteine was obtained from BLD Pharmatech GmbH. Anhydrous dimethylacetamide (DMAc) was obtained from Acros (Geel, Belgium). S‐Benzyl‐L‐cysteine, hydrogen peroxide, and n‐butylamine were purchased from Alfa Aesar (Kandel, Germany). PFD was obtained from Fluorochem Chemicals (Derbyshire, UK). Methanol, ethyl acetate and diethyl ether were purchased from Fisher Scientific (Schwerte, Germany). Finally, n‐hexane and dichloromethane were obtained from VWR International (Darmstadt, Germany) and acetonitrile was purchased from Carl Roth (Karlsruhe, Germany).
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Publication 2024
All reagents and solvents were of reagent-grade quality, procured from reputable commercial suppliers, and used without further purification. Bisphenol A was obtained from Showa (Menlo, GA, USA) while 2,6-dimethylphenol was purchased from Aldrich (St. Louis, MO, USA). Copper(I) bromide was purchased from Riedel-de Haën (Seelze near Hanover, Germany). DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and N-Butyldimethylamine (DMBA) were obtained from TCI (Tokyo, Japan). Trifluoromethanesulfonic acid (TfOH), p-toluenesulfonic acid monohydrate (p-TSA), phenylacetyl chloride, benzoyl chloride, and acetyl chloride were purchased from Alfa Aesar (Haverhill, MA, USA). Lauroyl chloride was obtained from Acros (Waltham, MA, USA).
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Publication 2024

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Trifluoromethanesulfonic acid is a strong organic acid with the chemical formula CF3SO3H. It is a colorless, odorless, and viscous liquid that is soluble in water and organic solvents. The compound is commonly used as a reagent in organic synthesis and as a catalyst in various chemical reactions.
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Diethyl ether is a colorless, volatile, and highly flammable liquid. It is commonly used as a laboratory solvent and reagent in various chemical processes and experiments.
Trifluoromethanesulfonic acid is a strong, colorless, and corrosive liquid. It is a sulfonic acid with the chemical formula CF3SO3H. This compound is commonly used as a strong acid catalyst in various organic synthesis reactions.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
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Trifluoroacetic acid is a colorless, corrosive liquid commonly used as a reagent in organic synthesis and analytical chemistry. It has the chemical formula CF3COOH.
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Acetic acid is a colorless, vinegar-like liquid chemical compound. It is a commonly used laboratory reagent with the molecular formula CH3COOH. Acetic acid serves as a solvent, a pH adjuster, and a reactant in various chemical processes.
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Ethyl acetate is a chemical compound commonly used in laboratory settings. It is a colorless, volatile liquid with a sweet, fruity odor. Ethyl acetate's core function is as a solvent, useful for a variety of applications in research and scientific analysis.
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Trifluoromethanesulfonic acid (TFMSA) is a strong organic acid used as a laboratory reagent. It is a clear, colorless, and fuming liquid. TFMSA has a high acidity and is commonly used in organic synthesis reactions as a catalyst or dehydrating agent.
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Potassium carbonate (K2CO3) is a white, crystalline, water-soluble chemical compound. It is commonly used as a pH regulator, buffer, and precipitating agent in various laboratory applications.

More about "Trifluoromethanesulfonic acid"

Trifluoromethanesulfonic acid (TFMSA), also known as triflic acid, is a powerful and versatile organic sulfonic acid with the chemical formula CF3SO3H.
This colorless, odorless liquid is miscible with water and many organic solvents, making it a highly useful compound in a variety of chemical applications.
Researchers often utilize TFMSA as a catalyst, dehydrating agent, and electrophilic reagent in organic synthesis, polymer chemistry, and materials science.
Its unique properties, including high acidity and reactivity, make it a valuable tool for chemists and researchers.
When working with TFMSA, it's important to consider related chemicals and solvents, such as diethyl ether, methanol, α-pinene, trifluoroacetic acid, acetic acid, and ethyl acetate.
Potassium carbonate (K2CO3) is also a common reagent used in conjunction with TFMSA.
PubCompare.ai's AI-driven optimization tools can help researchers easily locate and identify the best protocols and products from literature, preprints, and patents, ensuring reproducible and accurate results in their work with trifluoromethanesulfonic acid.
The platform's innovative solutions can streamline the research process and enhance the overall efficacy of TFMSA-related experiments and investigations.