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| | Trifluoromethanesulfonic anhydride Basic information |
| | Trifluoromethanesulfonic 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 | | color | Clear colorless to light brown | | Specific Gravity | 1.677 | | 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 | Trifluoromethanesulfonic anhydride(358-23-6) | | EPA Substance Registry System | Methanesulfonic acid, trifluoro-, anhydride (358-23-6) |
| Hazard Codes | C | | Risk Statements | 14-21/22-34-35-22-40 | | Safety Statements | 26-36/37/39-43-45-8 | | RIDADR | UN 3265 8/PG 2 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Corrosive | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | I | | HS Code | 29049020 | | Toxicity | LD50 orally in Rabbit: 1012 mg/kg |
| | Trifluoromethanesulfonic anhydride Usage And Synthesis |
| Chemical Properties | clear colorless to light brown liquid | | Uses | Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group. | | Uses | Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides. | | Definition | ChEBI: Triflic anhydride is an organosulfonic anhydride. It is functionally related to a triflic acid. | | 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.] |
| | Trifluoromethanesulfonic anhydride Preparation Products And Raw materials |
| Raw materials | Phosphorus pentoxide-->Trifluoromethanesulfonic acid-->Benzenesulfonic acid, 4-methyl-, anhydride with trifluoromethanesulfonic acid (9CI)-->bromine trifluoromethanesulfonate-->FLUOROTRIBROMOMETHANE-->TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER | | Preparation Products | (S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-7,7'-BIS(DIPHENYLPHOSPHINO)-1,1'-SPIROBIINDANE-->(R)-(+)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-(+)-7,7'-BIS[DI(4-METHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97%-->1-FLUORO-4-(TRIFLUOROMETHYLTHIO)BENZENE-->(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL-->(R)-(+)-TolBINAP-->1-(3-AMINO-PYRIDIN-2-YL)-ETHANONE-->(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->N-Phenyl-bis(trifluoromethanesulfonimide)-->5-AMINO-1,2,3-THIADIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->3,5-DIMETHYLISOXAZOL-4-YL ISOCYANATE-->2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE-->Troglitazone |
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