66178-41-4

Basic information

• Product Name: TRIFLUOROMETHANESULFONIC ACID-D
• Synonyms: DEUTEROTRIFLUOROMETHANESULFONIC ACID;TRIFLUOROMETHANESULFONIC ACID-D;trifluoromethanesulphonic (2H)acid;TRIFLUOROMETHANESULFONIC ACID-D, 98 ATOM % D;deuterotrifluormethansulfonic acid;Trifluoromethane(2H)sulfonic acid;Einecs 266-221-1;Methanesulfonic acid-D, 1,1,1-trifluoro-
• CAS NO: 66178-41-4
• Molecular Formula: CDF3O3S
• Molecular Weight: 151.08
• EINECS: 266-221-1
• Mol File: 66178-41-4.mol

Chemical Properties

• Boiling Point: 162 °C(lit.)
• Flash Point: °C
• Appearance: /
• Density: 1.708 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.14mmHg at 25°C
• Refractive Index: 1.354
• CAS DataBase Reference: TRIFLUOROMETHANESULFONIC ACID-D(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROMETHANESULFONIC ACID-D(66178-41-4)
• EPA Substance Registry System: TRIFLUOROMETHANESULFONIC ACID-D(66178-41-4)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-22
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 66178-41-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Trifluoromethanesulfonic Acid-d is used as a deuterated catalyst for esterification reactions in the chemical synthesis industry. The incorporation of deuterium in the acid allows for the study of reaction kinetics and mechanisms, providing a deeper understanding of the esterification process and potentially leading to more efficient and selective synthetic methods.
Used in Analytical Chemistry:
In the field of analytical chemistry, Trifluoromethanesulfonic Acid-d is employed as a deuterated reagent for the analysis of various organic compounds. The presence of deuterium in the molecule can enhance the detection and identification of specific compounds through techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy, leading to more accurate and reliable analytical results.
Used in Pharmaceutical Research:
Trifluoromethanesulfonic Acid-d is utilized in pharmaceutical research as a deuterated catalyst for the synthesis of deuterated drug candidates. The deuterated versions of these compounds can offer improved pharmacokinetic properties, such as increased stability and bioavailability, as well as potentially reduced side effects. This makes CF3SO3D a valuable tool in the development of new and improved pharmaceuticals.
Used in Material Science:
In the field of material science, Trifluoromethanesulfonic Acid-d is used as a deuterated catalyst for the synthesis of deuterated polymers and other materials. The incorporation of deuterium can lead to changes in the physical and chemical properties of these materials, such as enhanced thermal stability and improved mechanical properties, which can be beneficial for various applications, including aerospace, electronics, and energy storage.

InChI:InChI=1/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)/i/hD

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 507-20-0 tertiary butyl chloride 
• 1076-43-3 benzene-d6 
• 2923-28-6 silver trifluoromethanesulfonate 

Downstream Products

• 14177-93-6 trans-platinum(triethylphosphine)₂(chloro)₂ 
• 118275-33-5 rhenium(III)(oxo)(hydride)bis(2-butyne) 
• 187737-37-7 propene 
• 328390-57-4 Pt(CH₃)(C₂₀H₁₂F₁₂N₂)(C⁽²⁾H₃CN)⁽¹⁺⁾ 
• 372954-94-4 RuHCH₃CN(P(C₆H₅)3)2C₇H₈⁽¹⁺⁾ 
• 173170-88-2 [(C₆H₅⁽²⁾H)Mo(((P(C₆H₅)2)CH₂)3CCH₃)H]⁽¹⁺⁾ 

Relevant articles and documents

The effect of deuteration on the keto-enol equilibrium and photostability of the sunscreen agent avobenzone

The remarkable properties of deuterium have led to many exciting and favourable results in enhancing material properties, for applications in the physical, medical, and biological sciences. Deuterated isotopologues of avobenzone, a sunscreen active ingredient, were synthesised to examine for any changes to the equilibrium between the diketone and enol isomers, as well as their UV photostability and photoprotective properties. Prior to UV irradiation, deuteration of the diketone methylene/enol moiety (i.e. avobenzone-d2) led to an increase in the % diketone compared to non-deuterated, determined by 1H NMR experiments in CDCl3 and C6D12. This can be rationalised from two angles; mechanistically by a deuterium kinetic isotope effect for the CH vs. CD abstraction step during tautomerisation from the diketone to the enol, and a weaker chelating hydrogen bond for the enol when deuterated allowing increased equilibration to the diketone. Avobenzone-d2 was further examined by solid state 13C NMR. The higher % diketone for avobenzone-d2 was postulated to favour increased photodegradation by a non-reversible pathway. This was investigated by UV irradiation of the avobenzone isotopologues in C6D12, both in real time in situ within the NMR by fibre optic cable as well as ex situ using sunlight. An increase in the relative amount of photoproducts for avobenzone-d2 compared to non-deuterated was observed by 1H NMR upon UV irradiation ex situ. Overall, the study demonstrates that deuteration can be applied to alter complex equilibria, and has potential to be manifested as changes to the properties and behaviour of materials.

Dimensional Reduction of Lewis Acidic Metal-Organic Frameworks for Multicomponent Reactions

Owing to hindered diffusions, the application of porous catalytic materials has been limited to relatively simple organic transformations with small substrates. Herein we report a dimensional reduction strategy to construct a two-dimensional metal-organic framework (MOF), Zr6OTf-BTB, with 96% accessible Lewis acidic sites as probed by the bulky Lewis base pivalonitrile. With nearly free substrate accessibility, Zr6OTf-BTB outperformed two three-dimensional MOF counterparts of similar Lewis acidity (Zr6OTf-BPDC and Zr6OTf-BTC) in catalyzing sterically hindered multicomponent reactions (MCRs) for the construction of tetrahydroquinoline and aziridine carboxylate derivatives with high turnover numbers (TONs). Zr6OTf-BTB was also superior to the homogeneous benchmark Sc(OTf)3 with nearly 14 times higher TON and 9 times longer catalyst lifetime. Furthermore, the topology-activity relationships in these Zr-based Lewis acidic MOFs were rationalized by comparing their Lewis acidity, numbers of Lewis acidic sites, and sterically accessible Lewis acidic sites. Zr6OTf-BTB was successfully used to construct several bioactive molecules via MCRs with excellent efficiency. This dimensional reduction strategy should allow the development of other MOF catalysts for synthetically useful and complicated organic transformations.

Dicationic Thiolate-Bridged Diruthenium Complexes for Catalytic Oxidation of Molecular Dihydrogen

Dicationic thiolate-bridged diruthenium complexes bearing sterically bulky alkane substituents on the thiolate ligands such as [Cp?Ru(μ-SiPr)2Ru(OH2)Cp?](OTf)2 have been found to work as effective catalysts toward oxidation of molecular dihydrogen into protons and electrons in protic solvents such as water and methanol. DFT calculations indicate that the sterically bulky alkane substituent in the complex plays an important role in facilitating the reaction step of the coordination of molecular dihydrogen.

Hidden Bronsted acid catalysis: Pathways of accidental or deliberate generation of triflic acid from metal triflates

The generation of a hidden Bronsted acid as a true catalytic species in hydroalkoxylation reactions from metal precatalysts has been clarified in case studies. The mechanism of triflic acid (CF3SO3H or HOTf) generation starting either from AgOTf in 1,2-dichloroethane (DCE) or from a Cp*RuCl2/AgOTf/phosphane combination in toluene has been elucidated. The deliberate and controlled generation of HOTf from AgOTf and cocatalytic amounts of tert-butyl chloride in the cold or from AgOTf in DCE at elevated temperatures results in a hidden Bronsted acid catalyst useful for mechanistic control experiments or for synthetic applications.

Spectroscopic Studies on Monofluoroammonium Salts

The NMR, IR and Raman spectra of several NH3F(+)X(-) salts are reported.The preparation of NH3F(+)SO3Cl(-) and NH3F(+)SO3F(-) is described. - Key words: NMR Spectra, Raman Spectra, IR Spectra