Triflic acid

Manufactured by Merck Group

Sourced in Germany, China

Triflic acid is a strong superacid with the chemical formula HSO3CF3. It has a high acid strength and is commonly used as a catalyst and proton source in organic synthesis and other chemical processes. The main function of triflic acid is to provide a highly acidic environment for various chemical reactions.

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Trifluoromethanesulfonic acid (triflic acid (2 citations)

10 protocols using triflic acid

Synthesis of Poly(L-Lactide) via Ring-Opening Polymerization

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l,l-Lactide (LA) was purchased from
Purac (99% Netherlands), crystallized from 2-propanol and stored under
reduced pressure. Paraformaldehyde (99%), p-toluenesulfonic
acid (pTSA, 98%), 3-allyloxypropane-1,2-diol (98%), 3-chloropropane-1,2-diol
(98%), triflic acid (99%), phosphorus pentoxide (P₂O₅), propanethiol (99%), mercaptoethanol (95%), thioglycolic
acid (98%), propargyl glycidyl ether (98%), propargyl alcohol (97%),
copper (I) bromide, pentamethyldiethylenetriamine (95%, PMDTA), and
sodium azide were purchased from Merck and used without further purification.
Butan-1,4-diol (99%, Acros) was used as received. AIBN was purchased
from Sigma-Aldrich and crystallized from ethanol at 40 °C. Methylene
chloride from POCH was distilled over P₂O₅ and
maintained under a vacuum. Toluene (95%), hexane (95%), diethyl ether
(98%), and HCl (35%) were purchased from POCH (Gliwice, Poland) and
used as received. Anhydrous ethylene glycol (ethane-1,2-diol) (<99.9%,
Sigma-Aldrich) was used as received.

Cichoń K., Bak-Sypien I.I., Basko M, & Kost B. (2023). Synthesis and Characterization of Functionalized Polylactides Containing Acetal Units. Macromolecules, 56(17), 6951-6967.

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Synthesis and Purification of Polylactides

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l,l-lactide and d,d-lactide (99%, Purac, Gorkum, Netherlands) were consecutively crystallized from dry 2-propanol and purified just before use by sublimation in vacuo (10⁻³ mbar, 85 °C). Triflic acid (trifluorometanosulfonic acid, 98% Merck, Darmstadt, Germany) was used without further purification. Methylene chloride was distilled over P₂O₅ and stored under a vacuum over molecular sieves. Methanol, 2-propanol and THF (POCH, Gliwice, Poland, pure p.a. grade) and hexan-1-6-diol (Sigma Aldrich, Saint Louis, Missouri, USA), sodium acetate (99%, Merck, Darmstadt, Germany), acetic acid and CaO (98%, Merck, Darmstadt, Germany) were used as received. Phosphate buffer saline (pH 7.4, 0.1 M) and Tris buffer (pH 8.7, 0.1 M) were purchased from Merck (Darmstadt, Germany) in powder form and prepared according to the manufacturer’s instructions. Acetate buffer (pH 5.5, 0.1 M) was prepared as follows: 7.721 g of sodium acetate, and 352 mg of glacial acetic acid was dissolved in 1L of water.

Gonciarz W., Chmiela M., Kost B., Piątczak E, & Brzeziński M. (2023). Stereocomplexed microparticles loaded with Salvia cadmica Boiss. extracts for enhancement of immune response towards Helicobacter pylori. Scientific Reports, 13, 7039.

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Synthesis of Palladium Nanocatalyst

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Titanium isopropoxide (TTIP), palladium nitrate dihydrate, tetrahydrofuran (THF), and triflic acid (TFC) were obtained from Sigma-Aldrich (Shanghai, China) and used without any further purification.

Altaf A., Sohail M., Nafady A., Siddique R.G., Shah S.S, & Najam T. (2023). Facile Synthesis of PdO.TiO2 Nanocomposite for Photoelectrochemical Oxygen Evolution Reaction. Molecules, 28(2), 572.

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Synthesis of Photocurable PCL-based Hydrogels

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Poly(ε-caprolactone) diol (PCL₉₀-diol; M_n ~10 k g/mol), trimethylamine (Et₃N), acryloyl chloride, 4-dimethylaminopyridine (DMAP), 2,2-dimethoxy-2-phenylacetophenone (DMP), 1-vinyl-2-pyrrolidinone (NVP), potassium carbonate (K₂CO₃), sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium chloride (NaCl), octamethylcyclotetrasiloxane (D₄), triflic acid, hexamethyldisilazane (HMDS), ε-caprolactone, stannous 2-ethylhexanoate, sodium chloride (NaCl), sodium bicarbonate (NaCO₃), potassium chloride (KCl), dipotassium hydrogen phosphate trihydrate (K₂HPO₄·3H₂O), magnesium chloride hexahydrate (MgCl₂·6H₂O), calcium chloride (CaCl₂), sodium sulfate (Na₂SO₄), phosphate buffered saline (PBS; pH 7.4), and tris(hydroxymethyl)aminomethane were obtained from Sigma-Aldrich. Anhydrous magnesium sulfate (MgSO₄) was obtained from Thermo Fisher Scientific. Tetramethyldisiloxane (tetra-SiH), tetrakis(dimethylsiloxy)siloxane (tetrakis-SiH), and platinum-divinyl-tetramethyldisiloxane complex in xylene (Karstedt’s catalyst) were obtained from Gelest. Reagent-grade dichloromethane (CH₂Cl₂) and NMR-grade CDCl₃ were dried over 4 Å molecular sieves prior to use.

Beltran F.O., Houk C.J, & Grunlan M.A. (2021). Bioactive Siloxane-Containing Shape-Memory Polymer (SMP) Scaffolds with Tunable Degradation Rates. ACS biomaterials science & engineering, 7(4), 1631-1639.

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Synthesis of Aromatic Compounds using Diverse Reagents

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Acetone, acetonitrile, chloroform, dichloromethane, methanol, tetrahydrofuran (THF), toluene, and 1,4-dioxane were purchased from Fisher chemicals. 1-ethynyl-4-fluorobenzene and 1,3,5-tri-(4-aminophenyl)benzene were purchased from TCI. 1-ethynyl-4-(trifluoromethyl)benzene as purchased from 1Click Chemistry Stock Products. Methyl 4-ethynyl benzoate was purchased from AK scientific. 2,5-Dimethoxyterephthalaldehyde were purchased from Carbosynth chemicals. 2,4-diphenyl-quinoline were purchased from EnamineStore. Phenylacetylene, 4-ethynyl benzonitrile, boron trifluoride diethyl etherate, triethylamine were purchased from Alfa Aesar chemicals. Chloranil, triflic acid, 1,3,5-triformylbenzene, benzidine, mesitylene, o-dichlorobenzene, n-butanol were purchased from Sigma Aldrich chemicals.

Li X., Zhang C., Cai S., Lei X., Altoe V., Hong F., Urban J.J., Ciston J., Chan E.M, & Liu Y. (2018). Facile transformation of imine covalent organic frameworks into ultrastable crystalline porous aromatic frameworks. Nature Communications, 9, 2998.

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Synthesis of Sn0.39Ti0.61O2·TiO2 Nanocomposite

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Tin chloride, titanium
isopropoxide, triflic acid (TFC), and tetrahydrofuran (THF) were obtained
from Sigma-Aldrich and used without any purification. The detailed
synthesis procedure of Sn_0.39Ti_0.61O₂·TiO₂ along several other new nanocomposites has
been reported recently.⁵⁴ Briefly, tin(IV)
chloride and titanium isopropoxide as precursors for the Sn_0.39Ti_0.61O₂·TiO₂ composite were
added to 25 mL of tetrahydrofuran (THF), and polymerization of THF
was initiated by adding 0.5 mL of triflic acid (TFC) as shown in the
equation. In a 50 mL round-bottom flask, tin(IV) chloride pentahydrate
(0.01 M, 0.043 mL) and titanium isopropoxide (0.01 M, 3.03 mL) were
mixed in 25 mL of THF at 25 °C. Then, 0.5 mL of TFC was added
to initiate the polymerization of THF. Slow polymerization of THF
was allowed to occur with constant stirring at 25 °C for 4 h.
After the formation of polymeric gel, whole reaction products were
transferred to a crucible and placed in a furnace. The calcination
was performed by raising the temperature to 500 °C at a rate
of 4 °C per min and held there for 2 h. After pyrolysis, the
catalytic material was cooled to room temperature and stored in glass
vials.

Sohail M., Baig N., Sher M., Jamil R., Altaf M., Akhtar S, & Sharif M. (2020). A Novel Tin-Doped Titanium Oxide Nanocomposite for Efficient Photo-Anodic Water Splitting. ACS Omega, 5(12), 6405-6413.

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Synthesis of Functionalized Organic Compounds

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Pd(OAc)₂ (Sigma, 97%), SPhos (TCI Europe, >98%), K₃PO₄ (Sigma, ≥98%), ICl (Sigma, 1 M solution in CH₂Cl₂), Pd(PPh₃)₂Cl₂, (Sigma, 98%), CuI (Sigma, 98%), ethynyltrimethylsilane, (Sigma, 98%), tetrabutylammonium fluoride (Sigma, 1 M THF), o-xylene (Sigma, anhydrous 97%), FeCl₃, (Sigma, anhydrous for synthesis), CH₃NO₂ (Sigma, absolute, over molecular sieve, ≥98.5%), B₂Pin₂, (Combi-Blocks, 98%), Pd(dppf)Cl₂ (Sigma, not specified), KOAc (Sigma, anhydrous ≥99%), 1,4-dioxane (Thermo Scientific Chemicals, anhydrous 99.8%), Pd(PPh₃)₄ (Sigma, 99%), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (Thermo Scientific Chemicals, ≥98%), triflic acid (Sigma, ≥ 99%), AgNO₃ (Sigma, ≥99%), and tetra-n-butylammonium hexafluorophosphate (Sigma, 98%) were used as received. 1,4-diiodo-2,5-bis(trimethylsilyl)benzene^{51 (link)} and 2,5-diphenyl-3,4-di(4-tert-butylphenyl)-cyclopentadien-1-one^{52 (link)} were synthesized according literature procedures. Solvents were purchased from SDS Carlo Erba, Aldrich, and Fisher Scientific and were used as received. For synthesis, unstabilized CH₂Cl₂ (CaH₂, N₂), toluene (K/benzophenone, N₂), THF (K/benzophenone, N₂), Et₃N (CaH₂, N₂), and Et₂O (CaH₂, N₂) were distilled before use.

Medina-Lopez D., Liu T., Osella S., Levy-Falk H., Rolland N., Elias C., Huber G., Ticku P., Rondin L., Jousselme B., Beljonne D., Lauret J.S, & Campidelli S. (2023). Interplay of structure and photophysics of individualized rod-shaped graphene quantum dots with up to 132 sp² carbon atoms. Nature Communications, 14, 4728.

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Synthesis of PDMS-based Macro-CTA

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2,2’- Azobis(2-methylpropionitrile) (AIBN) (Sigma-Aldrich) was purified by recrystallization from methanol prior to use. N-Vinylcaprolactam (VCL) (Sigma-Aldrich) and tetrahydrofuran (Fisher) was distilled before reaction. Potassium ethyl xanthate, 2-bromopropionyl bromide, diethyl ether, hexane, dichloromethane, calcium sulfate anhydrous, and dialysis tubing (MWCO 5 kDa) (Fisher) were used as received. Bis(hydroxyalkyl) poly(dimethylsiloxane) (PDMS₆₅, Mn = 5600 Da) was purchased from Sigma-Aldrich. Triflic acid was purchased from Sigma-Aldrich.

Yang Y., Alford A., Kozlovskaya V., Zhao S., Joshi H., Kim E., Qian S., Urban V., Cropek D., Aksimentiev A, & Kharlampieva E. (2019). Effect of temperature and hydrophilic ratio on the structure of poly(N-vinylcaprolactam)-block-poly(dimethylsiloxane)-block-poly(N-vinylcaprolactam) polymersomes. ACS applied polymer materials, 1(4), 722-736.

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Drying and Purification of Organic Reagents

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Dichloromethane was obtained from Biosolve and 1,3-dioxolane (99.5%) was obtained from Acros. Both were dried prior to usage by distillation over CaH₂ (93%, 10–100 mm pieces, up to 10% powder, Acros), and kept on molecular sieves (3 Å, Sigma-Aldrich). Triflic acid (99%) was obtained from Sigma-Aldrich and purified by vacuum distillation (76 °C, 40 mbar) prior to usage. Ethylene glycol (99.8%) was obtained as a dry solvent from Sigma-Aldrich. Triethylamine (>99%), trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]-malonitrile (>98%), potassium trifluoroacetate (98%), triphenylphosphine (PPh₃) (99%) and chromium(iii) acetylacetonate (97%) were obtained from Sigma-Aldrich and used as received. The remaining solvents were obtained from Biosolve and used as received.

Coenen A.M., Harings J.A., Ghazanfari S., Jockenhoevel S, & Bernaerts K.V. (2020). Formation of cyclic structures in the cationic ring-opening polymerization of 1,3-dioxolane. RSC Advances, 10(16), 9623-9632.

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Synthesis and Characterization of Triazine Compounds

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All reagents
used in this study were of analytical grade and used without further
purification. 2,4-Diamino-6-phenyl-1,3,5-traizine (CAS # 91-76-6),
triflic acid (CAS # 1493-13-6), 1,2-dichloroethane (CAS # 107-06-2),
and ethanol (CAS # 64-17-5) were purchased from Sigma-Aldrich, while
4,4-bis(methoxymethyl)biphenyl (CAS # 3753-18-2) was purchased
from TCI Chemicals. ¹²CO₂ (grade 4.0, >99.99%),
N₂ (grade 5.0, >99.999%), and He (grade 5.0, >99.999%)
were purchased from Linde Gas Benelux. ¹³CO₂ (99.0 at. % ¹³C) was purchased from Aldrich.

Schukraft G.E., Itskou I., Woodward R.T., Van Der Linden B., Petit C, & Urakawa A. (2022). Evaluation of CO2 and H2O Adsorption on a Porous Polymer Using DFT and In Situ DRIFT Spectroscopy. The Journal of Physical Chemistry. B, 126(40), 8048-8057.

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