Trimethylsilyl trifluoromethanesulfonate (TMSOTf) - ≥99% , CAS No.27607-77-8

CAS: 27607-77-8 Cat. No.: T398981 Molecular Weight: 222.26 Beilstein Registry Number: 1868911 EC Number: 248-565-4 PubChem CID: 65367

GRADE & PURITY ≥99%

Synonyms

TMSOTf | Methanesulfonic acid, trifluoro-, trimethylsilyl ester | AKOS005063796 | J-525112 | MFCD00000406 | trimethylsilyl trifluoromethansulfonate | trimethylsilyl-trifluoromethansulfonate | Trimethylsilyl triflate | trimethylsilyltrifluoromethanesulfona

Storage

Store at 2-8°C,Argon charged,Desiccated

Shipped In

Wet ice

Overview

Trimethylsilyl trifluoromethanesulfonate is a strong Lewis acid catalyst and efficient silylating agent.
Usually used in a Dieckmann-like cyclization of ester-imides and diesters,and also used to prepare difluoroboron triflate etherate a powerful Lewis acid especially in acetonitrile solvent.

Specifications

Synonyms

TMSOTf | Methanesulfonic acid, trifluoro-, trimethylsilyl ester | AKOS005063796 | J-525112 | MFCD00000406 | trimethylsilyl trifluoromethansulfonate | trimethylsilyl-trifluoromethansulfonate | Trimethylsilyl triflate | trimethylsilyltrifluoromethanesulfona

Specifications & Purity

≥99%

Storage

Store at 2-8°C, Argon charged, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• IUPAC Name: trimethylsilyl trifluoromethanesulfonate
• InChIKey: FTVLMFQEYACZNP-UHFFFAOYSA-N
• INCHI: 1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
• Isomeric SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• WGK Germany: 3
• PubChem CID: 65367
• UN Number: 2920
• Packing Group: II
• Molecular Weight: 222.26
• Beilstein: 1868911
• Reaxy-Rn: 1868911

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic sulfonic acids and derivatives
      • Subclass Organosulfonic acids and derivatives
        • Level5 Alkanesulfonic acids and derivatives
          • Level6 Alkanesulfonic acids
            • Level7 Trifluoromethanesulfonates

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic sulfonic acids and derivatives
• Subclass: Organosulfonic acids and derivatives
• Intermediate Tree Nodes: Alkanesulfonic acids and derivatives - Alkanesulfonic acids
• Direct Parent: Trifluoromethanesulfonates
• Alternative Parents: Trialkylheterosilanes Sulfonyls Methanesulfonates Trihalomethanes Organic metalloid salts Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trifluoromethanesulfonate - Methanesulfonate - Trialkylheterosilane - Sulfonyl - Trihalomethane - Organoheterosilane - Organic metalloid salt - Alkyl fluoride - Hydrocarbon derivative - Halomethane - Organic salt - Organosilicon compound - Organic oxide - Organosulfur compound - Organofluoride - Organohalogen compound - Organic oxygen compound - Alkyl halide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trifluoromethanesulfonates. These are alkanesulfonic acids, that contain a sulfonate group that is substituted with a trifluoromethyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Miscible with aliphatic, aromatic hydrocarbons, haloalkanes and ethers. Immiscible with water.
• Sensitivity: Moisture & Air sensitive.
• Refractive Index: 1.36-1.362
• Flash Point(°F): 77 °F
• Flash Point(°C): 25℃
• Boil Point(°C): 140°C
• Molecular Weight: 222.260 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 221.999 Da
• Monoisotopic Mass: 221.999 Da
• Topological Polar Surface Area: 51.800 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 244.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Xiaoyan Zhang, Yufei Ren, Juyan Zhang, Xiangkun Wu, Chunhai Yi, Lan Zhang, Suitao Qi.  (2022)  Synergistic Effect of TMSPi and FEC in Regulating the Electrode/Electrolyte Interfaces in Nickel-Rich Lithium Metal Batteries.  ACS Applied Materials & Interfaces,      [PMID:35195414] [10.1021/acsami.1c24971]

2. Jing-Fang Shi, Ping Wu, Xiao-Li Cheng, Xiao-Yi Wei, Zi-Hua Jiang.  (2020)  Synthesis and Cytotoxic Property of Annonaceous Acetogenin Glycoconjugates.  Drug Design Development and Therapy,      [PMID:33235438] [10.2147/DDDT.S259547]

3. XiaoNing Gao, YanXiao Zhang, Wei Fu, Hong Zhou, Lu Feng.  (2024)  Strong Lewis acid MOF material for efficient and clean diosgenin extraction from total saponins in D. zingiberensis C. H. Wright.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2024.113860]

4. Yang Xiao, Wei Li, Changzhen Qu, Kaixuan Li, Yangtian Yan, Dengyun Zhai, Feiyu Kang.  (2026)  A Sacrificial Additive Strategy: Integrates Scavenging and Byproduct Utilization for High-Voltage Lithium Batteries.  Small,      [PMID:] [10.1002/smll.73506]