358-23-6 Usage
Description
Trifluoromethanesulfonic anhydride, also known as triflyl anhydride or triflate anhydride, is a strong electrophile and a potent reagent in organic chemistry. It is a clear colorless to light brown liquid that is highly reactive due to its ability to introduce the triflyl group into various chemical compounds.
Uses
Used in Chemical Synthesis:
Trifluoromethanesulfonic anhydride is used as a reagent for introducing the triflyl group in chemical synthesis. Its strong electrophilic nature allows it to react with a wide range of substrates, making it a versatile tool in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trifluoromethanesulfonic anhydride is used as a reagent for the conversion of phenols and imines into triflic ester and NTf groups. This conversion is crucial for the synthesis of various pharmaceutical compounds, as the triflyl group can be used to modulate the reactivity and selectivity of the resulting products.
Used in Synthesis of Alkyl and Vinyl Triflates:
Trifluoromethanesulfonic anhydride is used as a reagent in the preparation of alkyl and vinyl triflates. These triflates are important intermediates in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Stereoselective Synthesis:
Trifluoromethanesulfonic anhydride is used as a reagent for the stereoselective synthesis of mannosazide methyl uronate donors. These donors are key building blocks in the synthesis of complex carbohydrate structures, which have applications in the development of new drugs and vaccines.
Used in Carbohydrate Chemistry:
In carbohydrate chemistry, trifluoromethanesulfonic anhydride acts as a catalyst for glycosylation with anomeric hydroxy sugars. This reaction is essential for the preparation of polysaccharides, which are important components of various biological systems and have potential applications in the development of new therapeutics and diagnostic tools.
Hazard
May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage.
Flammability and Explosibility
Notclassified
Synthesis
The synthesis of?Trifluoromethanesulfonic anhydride is as follows:A dry, 100-ml., round-bottomed flask is charged with 36.3 g. (0.242
mole) of trifluoromethanesulfonic acid (Note 1) and 27.3 g. (0.192 mole)
of phosphorus pentoxide (Note 2). The flask is stoppered and allowed to
stand at room temperature for at least 3 hours. During this period the
reaction mixture changes from a slurry to a solid mass. The flask is
fitted with a short-path distilling head and heated first with a stream
of hot air from a heat gun and then with the flame from a small burner.The flask is heated until no more trifluoromethanesulfonic anhydride
distills, b.p. 82–115°, yielding 28.4–31.2 g. (83–91%) of the anhydride,
a colorless liquid. Although this product is sufficiently pure for use
in the next step, the remaining acid may be removed from the anhydride
by the following procedure. A slurry of 3.2 g. of phosphorus pentoxide
in 31.2 g. of the crude anhydride is stirred at room temperature in a
stoppered flask for 18 hours. After the reaction flask has been fitted
with a short-path distilling head, it is heated with an oil bath,
yielding 0.7 g. of forerun, b.p. 74–81°, followed by 27.9 g. of the pure
trifluoromethanesulfonic acid anhydride, b.p. 81–84° .
storage
Store in a cool, dry, wellventilated area. ?Moisture sensitive.
Purification Methods
It can be freshly prepared from the anhydrous acid (11.5g) and P2O5 (11.5g, or half this weight) by setting aside at room temperature for 1hour, distilling off volatile products then distil it through a short Vigreux column. It is readily hydrolysed by H2O and decomposes appreciably after a few days to liberate SO2 and produce a viscous liquid. Store it dry at low temperatures. [Burdon et al. J Chem Soc 2574 1957, Beard et al. J Org Chem 38 373 1973, Beilstein 3 IV 35.]
Check Digit Verification of cas no
The CAS Registry Mumber 358-23-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 8 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 358-23:
(5*3)+(4*5)+(3*8)+(2*2)+(1*3)=66
66 % 10 = 6
So 358-23-6 is a valid CAS Registry Number.
InChI:InChI=1/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
358-23-6Relevant articles and documents
Dilithium bis[(perfluoroalkyl)sulfonyl]diimide salts as electrolytes for rechargeable lithium batteries
Geiculescu,Xie, Yuan,Rajagopal,Creager,DesMarteau
, p. 1179 - 1185 (2004)
A series of four different dilithium salts of structure F3 CSO2N(Li)SO2-(CF2)x -SO2N(Li)SO2CF3, with x = 2, 4, 6, 8 were synthesized and characterized in polyethylene-oxide-based solid polymer electrolytes. Each salt may be thought of as two bis[(perfluoroalkyl)sulfonyl]imide anions linked together by a perfluoroalkyl chain of a particular length. Taken together, this homologous series provides an opportunity to study the effects of linker chain length and degree of fluorination in dianionic (and ultimately polyanionic) salts on the properties, particularly the conductivity, of the salts in various solvating media. SPEs in polyethylene oxide were characterized using scanning calorimetry, X-ray diffraction, 1H and 19F NMR, and electrochemical impedance spectroscopy for SPEs prepared using ethylene-oxide-oxygen-to-lithium (EO:Li) ratios of 10:1 and 30:1. Trends in SPE ionic conductivity with anion structure revealed an unexpected trend whereby ionic conductivity is generally rising with increased length of the perfluoroalkylene linking group in the dianions. This trend could be the result of a decrease in dianion basicity that results in diminished ion pairing and an enhancement in the number of charge carriers with increasing anion fluorine content, thereby increasing ionic conductivity.
Synthesis of 1,3-dialkyl imidazolium ionic liquids containing difunctional and tetrafunctional perfluoroalkylsulfonyl imide anions
Hickman, Tom,Desmarteau, Darryl D.
, p. 11 - 15 (2012)
Direct methylation of imidazole using methylated difunctional or tetrafunctional perfluorosulfonyl imides renders excellent yields of the corresponding room temperature ionic liquids (RTILs). This methodology provides a simple, halide-free route to several novel RTILs containing multifunctional perfluorosulfonyl imide anions.
Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid
Driess, Matthias,Hermannsdorfer, André
supporting information, p. 13656 - 13660 (2021/05/03)
A facile synthesis and isolation of pristine silicon tetrakis(trifluoromethanesulfonate), Si(OTf)4, is reported, acting as the first neutral silicon-based Lewis superacid suitable towards soft and hard Lewis bases. Its OTf groups have a dual function: they are excellent leaving groups and modulate the degree of reactivity towards soft and hard Lewis bases. Exposed to soft Lewis donors, Si(OTf)4 leads to [L2Si(OTf)4] complexes (L=isocyanide, thioether and carbonyl compounds) with retention of all Si?OTf bonds. In contrast, it can cleave C?X bonds (X=F, Cl) of hard organic Lewis bases with a high tendency to form SiX4 (X=F, Cl) after halide/triflate exchange. Most notable, Si(OTf)4 allows a gentle oxydefluorination of mono- and bis(trifluoromethyl)benzenes, resulting in the formation of the corresponding benzoylium species, which are stabilized by the weakly coordinating [Si(OTf)6] dianion.
METHOD FOR PRODUCING FLUOROALKANESULFONIC ANHYDRIDE
-
Paragraph 0059-0061, (2014/11/12)
Disclosed is a method for producing a fluoroalkanesulfonic anhydride, which is characterized by that a reaction is conducted while kneading a fluoroalkanesulfonic acid and diphosphorus pentoxide at a temperature that is 40 °C or higher and is lower than 100 °C by using a kneader-type reactor having a maximum power of 1.0 kW or greater per an actual capacity of 100 L and equipped with at least two-shaft blades, that the fluoroalkanesulfonic anhydride to be generated is discharged, and that, while the residue in the reactor after the discharge is kneaded at a temperature that is 100 °C or higher and is lower than 140 °C, the unreacted fluoroalkylsulfonic acid is discharged, recovered and reused as the raw material. It is possible by this method to obtain a fluoroalkanesulfonic anhydride with a high yield.