Trifluoromethanesulfonic anhydride
Tf2O · TRIFLIC ANHYDRIDE · Trifluoromethylsulfonic anhydride · TFO2 · trifluoromethylsulfonyl trifluoromethanesulfonate · TRIFLUOROMETHANESULFONIC ACID ANHYDRIDE · TRIFLUOROMETHANESULPHONIC ANHYDRIDE · (trifluoroMethane)sulfonyl trifluoroMethanesulfonate
Identifiers & Physical Properties
| CAS No. | 358-23-6 |
|---|---|
| Molecular formula | C2F6O5S2 |
| Average molar mass | 282.14 g/mol |
| Monoisotopic mass | 281.90913442 g/mol |
| SMILES | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F |
| InChIKey | WJKHJLXJJJATHN-UHFFFAOYSA-N |
| PubChem CID | 67749 |
| ChEBI | CHEBI:48509 |
| EC No. | 206-616-8 |
| DTXSID | DTXSID501014629 |
Chemical & Physical Properties
| XLogP | 1.6 |
|---|---|
| Topological polar surface area | 94.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 11 |
| Rotatable bonds | 2 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 370 |
| Chemical classes | Other Classes -> Acid Anhydrides, Other |
| PFAS | PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compoundsPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008 |
| SpringerMaterials Properties | Schoenflies notation |
| Density | 1.677 @25 °C1.677 g/mL at 25 °C (lit.) |
| Vapor pressure | 8.0 [mmHg]8 [mm Hg] @20 °C8 mm Hg ( 20 °C) |
| Physical Description | Colorless hygroscopic liquid[Merck Index] Clear colorless liquid[Sigma-Aldrich MSDS] |
| Melting point | -80°C |
| Boiling point | 81-83 °C (lit.) |
| Vapor density | 5.2 (vs air) |
| Refractive index | n20/D 1.321(lit.) |
| RTECS number | PB2772000 |
| Flash point | 81-83°C |
| Storage conditions | Store below +30°C. |
| Solubility | Miscible with dichloromethane. Immiscible with hydrocarbons.reacts violently with water |
| Physical state | Liquid |
| Specific gravity | 1.677 |
| Color | Clear colorless to light brown |
| Sensitivity | Moisture Sensitive |
| BRN | 1813600 |
| Stability | Hygroscopic, Moisture Sensitive |
| InChI | 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 |
| InChIKey | WJKHJLXJJJATHN-UHFFFAOYSA-N |
| SMILES | FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F |
| LogP (partition coefficient) | 0.3 at 25℃ |
| CAS DataBase Reference | 358-23-6(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 8W034LHG1U |
| NIST Chemistry Reference | Trifluoromethanesulfonic anhydride(358-23-6) |
| EPA Substance Registry System | Methanesulfonic acid, trifluoro-, anhydride (358-23-6) |
| UNSPSC Code | 12352106 |
| NACRES | NA.22 |
| GHS pictogram | GHS03,GHS05,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H272-H302-H314-H335 |
| GHS precautionary statements | P210-P220-P280-P301+P312-P303+P361+P353-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 14-21/22-34-35-22-40 |
| Safety statements (S) | 26-36/37/39-43-45-8 |
| UN transport number | UN 3265 8/PG 2 |
| Water hazard class (WGK) | 3 |
| F | 10-21 |
| Hazard Note | Corrosive |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 4 OralEye Dam. 1Ox. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Packing group | I |
| Customs code | 29049020 |
| Storage class | 5.1B - Oxidizing hazardous materials |
| Toxicity | LD50 orally in Rabbit: 1012 mg/kg |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH272 (51.1%): May intensify fireoxidizer [Danger Oxidizing liquidsOxidizing solids]P210, P220, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 227 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Methanesulfonic acid, trifluoro-, anhydrideStatus: Active Update: 03-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/22478Trifluoromethanesulphonic anhydride: HSNO Approval: HSR004747 Approved with controls |
| Hazards summary | Reacts violently with waterCorrosive[Merck Index] Reacts violently with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion[Sigma-Aldrich MSDS] See Trifluoromethanesulfonic acid. |
| Hazard Classes and Categories | Ox. Liq. 2 (51.1%) |
| CSL Reaction Information | CSL00005TETRAHYDROFURAN + Triflic anhydrideCan polymerize, large exotherm. Avoid combination on larger scale.User-Reported6/29/1810/2/17 |
| Protective Action Criteria (PAC) | 3.0 [mg/m3]33 [mg/m3]200 [mg/m3] |
| Adverse effects | Dermatotoxin - Skin burns. |
| F | 10-21 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) |
Applications & Uses
Description
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, It has been widely used in synthetic chemistry due to its high electrophilicity. Given its high affinity towards O-nucleophiles, reaction with alcohols, carbonyls, sulfur phosphorus- and iodine oxides towards the formation of the corresponding triflates is strongly favored. 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[1-2].
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.