Trifluoromethanesulfonic anhydride - ≥98% , CAS No.358-23-6

CAS: 358-23-6 Cat. No.: T106649 Molecular Weight: 282.14 Beilstein Registry Number: 1813600 EC Number: 206-616-8

GRADE & PURITY ≥98%

Synonyms

EN300-50306 | MFCD00000408 | trifluoromethylsulfonic acid anhydride | trifluoro methanesulfonic anhydride | trifluoromethanesulfonic acid anhydride | trifluoro-methanesulfonic acid anhydride | trifluoromethane-sulfonic acid anhydride | UNII-8W034LHG1U | 1

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Widely used reagent for the synthesis of alkyl and vinyl triflates. Catalyst for glycosylation for synthesis of polysaccharides Reagent for stereoselective synthesis of mannosazide methyl uronate donors Activator for direct glycosylation with anomeric hydroxy sugars

Specifications

Synonyms

EN300-50306 | MFCD00000408 | trifluoromethylsulfonic acid anhydride | trifluoro methanesulfonic anhydride | trifluoromethanesulfonic acid anhydride | trifluoro-methanesulfonic acid anhydride | trifluoromethane-sulfonic acid anhydride | UNII-8W034LHG1U | 1

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
• IUPAC Name: trifluoromethylsulfonyl trifluoromethanesulfonate
• InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N
• INCHI: 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
• Isomeric SMILES: C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
• WGK Germany: 3
• UN Number: 3265
• Packing Group: II
• Molecular Weight: 282.14
• Beilstein: 1813600
• Reaxy-Rn: 1813600

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: Organosulfonic anhydrides Sulfonyls Methanesulfonates Trihalomethanes Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trifluoromethanesulfonate - Organosulfonic anhydride - Sulfonyl - Methanesulfonate - Trihalomethane - Organic oxygen compound - Organic oxide - Halomethane - Hydrocarbon derivative - Organosulfur compound - Organofluoride - Organohalogen compound - Alkyl halide - Alkyl fluoride - 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: organosulfonic anhydride

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 dichloromethane. Immiscible with hydrocarbons.
• Sensitivity: Heat sensitive,Hygroscopic
• Refractive Index: 1.32-1.323
• Flash Point(°C): 110°C
• Boil Point(°C): 81~84℃
• Melt Point(°C): -80°C
• Molecular Weight: 282.140 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 2
• Exact Mass: 281.909 Da
• Monoisotopic Mass: 281.909 Da
• Topological Polar Surface Area: 94.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 370.000
• 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

References

1. Bohong Yu, Yubo Liu, Yingxi Zhang, Linyi Xu, Kai Jin, Andi Sun, Xiuli Zhao, Yongjun Wang, Hongzhuo Liu.  (2023)  An SS31-rapamycin conjugate via RBC hitchhiking for reversing acute kidney injury.  BIOMATERIALS,      [PMID:37939640] [10.1016/j.biomaterials.2023.122383]

2. Zhang Yu, Zheng Jianzhi, Li Xijuan, Wu Ying, Zhang Ke.  (2023)  Stoichiometric Imbalance-promoted Step-growth Polymerization Based on Self-accelerating Three-component Reaction.  CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,  39  (5): (822-828).  [PMID:] [10.1007/s40242-023-3173-3]

3. Tao Sun, Qinjun Chen, Zheng Zhou, Chao Li, Teng Yu, Chen Jiang.  (2023)  A chemiluminescent reporter assisted by in-situ neutrophils for imaging O2− at inflammatory sites.  JOURNAL OF CONTROLLED RELEASE,      [PMID:37100207] [10.1016/j.jconrel.2023.04.035]

4. Chenfang Sun, Guangyuan Feng, Yaru Song, Shanshan Cheng, Shengbin Lei, Wenping Hu.  (2022)  Single Molecule Level and Label-Free Determination of Multibiomarkers with an Organic Field-Effect Transistor Platform in Early Cancer Diagnosis.  ANALYTICAL CHEMISTRY,      [PMID:35446018] [10.1021/acs.analchem.2c00897]

5. Rui Li, Xiaoqing Yin, Shiyi Zhang, Jinchu Yang, Mingqin Zhao.  (2021)  Preparation and pyrolysis of two Amadori analogues as flavor precursors.  JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS,      [PMID:] [10.1016/j.jaap.2021.105357]

6. Yudi Feng, Ke Jin, Jia Guo, Changchun Wang.  (2021)  All-carbocycle hydrocarbon thermosets with high thermal stability and robust mechanical strength for low-k interlayer dielectrics.  Polymer Chemistry,  12  (33): (4812-4821).  [PMID:] [10.1039/D1PY00877C]

7. Hua-Ming Xiao, Shuai Zhao, Ru-Ting Fan, Dilshad Hussain, Xian Wang.  (2021)  Simultaneous determination of short-chain fatty alcohols in aged oil and biodiesels by stable isotope labeling assisted liquid chromatography-mass spectrometry.  TALANTA,      [PMID:33838765] [10.1016/j.talanta.2021.122223]

8. Qingping Xin, Tianyu Liu, Zhao Li, Shaofei Wang, Yifan Li, Zhen Li, Jingyi Ouyang, Zhongyi Jiang, Hong Wu.  (2015)  Mixed matrix membranes composed of sulfonated poly(ether ether ketone) and a sulfonated metal–organic framework for gas separation.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2015.03.060]

9. Zhen Li, Guangwei He, Yuning Zhao, Ying Cao, Hong Wu, Yifan Li, Zhongyi Jiang.  (2014)  Enhanced proton conductivity of proton exchange membranes by incorporating sulfonated metal-organic frameworks.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2014.03.123]

10. Yuanqing Fu, Shan Hong, Duo Li, Songbai Liu.  (2013)  Novel Chemical Synthesis of Ginkgolic Acid (13:0) and Evaluation of Its Tyrosinase Inhibitory Activity.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:23701207] [10.1021/jf4012642]

11. Na Li, Jian Gao, Hongzhe Ni, Jialin Zhao, Kuirong Feng, Jingyi Wu, Yijia Lei, Yan Wang, Jiayao Yang, Shiyao Sun, Zhe Wang.  (2024)  Fluorinated Poly(thiophene-based aryl piperidinium) Anion-Exchange Membranes Containing Dual Cation–Dipole Interactions for Alkaline Fuel Cells.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.4c02735]

12. Liu Mu-Han, Sun Wei-Ting, Yang An-Qi, Wang Zhi, Chang Zong, Wang Ai-E, Huang Pei-Qiang.  (2025)  Streamlined synthesis of α-keto-, α-hydroxy- and α,α-difluorophosphonates from amides via electrophilic activation with trifluoromethanesulfonic anhydride.  Science China-Chemistry,      [PMID:] [10.1007/s11426-025-2935-3]