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Trifluoromethanesulfonic anhydride, also known as triflic anhydride, has proven to be an extraordinary reagent for a broad range of transformations.
As a commercially and readily available reagent, Triflic Anhydride has been widely used in synthetic chemistry due to its high electrophilicity.
Given Triflic Anhydride's high affinity towards O-nucleophiles, reaction with alcohols, carbonyls, sulfur phosphorus- and iodine oxides towards the formation of the corresponding triflates is strongly favored.
CAS: 358-23-6
MF: C2F6O5S2
MW: 282.14
EINECS: 206-616-8
Synonyms
Trifluoromethanesulfonic anhydlladium(0);Trifluoromethanesulfonic anhydride purum, >=98.0% (T);Trifluoromethanesulfonic anhydride solution 1 M in methylene chloride;Triflic anhydride solution;7561347, DT: 23.1 1.2016) RE-EXPORT;TRIFLUOROMETHANE SULFONIC ANHYDRIDE(ORIG INAL IMPORT VIDE BE.NO;Trifluoromethanesulfonic anhydride solution ;Methanesulfonic acid, trifluoro-, anhydride
As one of the premier leaving groups in organic chemistry, the generated triflates then open the door to various downstream transformations, including (but not limited to) substitution reactions, cross-coupling processes, redox reactions, and rearrangements.
Triflic anhydride is an organosulfonic anhydride.
Triflic Anhydride is functionally related to a triflic acid.
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF3SO2)2O.
Triflic Anhydride is the acid anhydride derived from triflic acid.
Triflic Anhydride is a strong electrophile, useful for introducing the triflyl group, CF3SO2.
Abbreviated Tf2O, triflic anhydride is the acid anhydride of the superacid triflic acid, CF3SO2OH.
Triflic Anhydride is supplied by Apollo Scientific across the UK and globally.
Triflic Anhydride (CAS number 358-23-6), also referred to as Triflic anhydride & Trifluoromethanesulphonic anhydride, is used for numerous applications including the conversion of phenols and imines into triflic esters and NTf groups.
Triflic Anhydride is a strong electrophile used for the introduction of triflyl group in chemical compound synthesis.
Triflic Anhydride serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors.
Triflic Anhydride is used in further industrial processes, serving as catalyst in glycosylation for synthesis of polysaccharides.
Triflic anhydride may be used to introduce a protective trifluoromethane sulfonyl group.
Triflic Anhydride is a strong activator of hydroxyl groups, for example in glycosidation reactions.
Triflic Anhydride is an efficient promoter for inversion configuration and for nucleophilic substitutions.
Triflic Anhydride may also be used as an activator of phenols or enols for the synthesis of aryl and vinyl triflates.
Triflic Anhydride Chemical Properties
Melting point: -80°C
Boiling point: 81-83 °C (lit.)
Density: 1.677 g/mL at 25 °C (lit.)
Vapor density: 5.2 (vs air)
Vapor pressure: 8 mm Hg ( 20 °C)
Refractive index: n20/D 1.321(lit.)
RTECS: PB2772000
Fp: 81-83°C
Storage temp.: Store below +30°C.
Solubility: Miscible with dichloromethane. Immiscible with hydrocarbons.
Form: Liquid
Specific Gravity: 1.677
Color: Clear colorless to light brown
Water Solubility: reacts violently with water
Sensitive: Moisture Sensitive
BRN: 1813600
Stability: Hygroscopic, Moisture Sensitive
InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N
LogP: 0.3 at 25℃
CAS DataBase Reference: 358-23-6(CAS DataBase Reference)
NIST Chemistry Reference: Triflic Anhydride (358-23-6)
EPA Substance Registry System: Triflic Anhydride (358-23-6)
Uses
Triflic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.
Triflic Anhydride is used to convert phenols and imine into triflic ester and NTf group.
Triflic Anhydride is a strong electrophile used for the introduction of triflyl group in chemical synthesis.
Triflic Anhydride serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors.
Triflic Anhydride acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.
Synthesis
The synthesis of Triflic 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 Triflic Anhydride 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° .
Preparation and uses
Triflic Anhydride is prepared by dehydration of triflic acid using P4O10.
Triflic anhydride is useful for converting ketones into enol triflates.
In a representative application, is used to convert an imine into a NTf group.
Triflic Anhydride will convert phenols into a triflic ester, which enables cleavage of the C-O bond.
Reactivity Profile
Electrophilic activation of tertiary and secondary amides with triflic anhydride (Tf2O; rifluoromethanesulfonic anhydride) under mild conditions gives rise to iminium and imino triflates, respectively, which could be utilized as versatile reagents to react with various C-, N-, O- and S-nucleophiles for the transformation of an amide function into different products.
Other oxygen-containing nucleophiles, such as sulfoxides and phosphorus oxides, could also undergo nucleophilic attack with Tf2O to generate thionium triflate, electrophilic P-species, and phosphonium triflate.
These highly active transient species could readily undergo nucleophilic substitution reactions for further diverse transformations.
Furthermore, owing to the strong electrophilic property, Tf2O is prone to react with relatively weak nucleophiles such as nitrile groups or some nitrogen-containing heterocyclic compounds.
In addition, Tf2O has also been used as an efficient radical trifluoromethylation and trifluorometh ylthiolation reagent through the release of SO2 or deoxygenation process for the synthesis of trifluoromethylated and trifluoromethylthiolated compounds.
Purification Methods
Triflic Anhydride 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.
Triflic Anhydride 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.
