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Trifluoromethanesulfonic anhydride structure
Trifluoromethanesulfonic anhydride structure

Trifluoromethanesulfonic anhydride

Iupac Name:trifluoromethylsulfonyl trifluoromethanesulfonate
CAS No.:358-23-6
Molecular Weight:282.138819
Introduction: Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group. View more+
1. Names and Identifiers
1.1 Name
Trifluoromethanesulfonic anhydride
1.2 Synonyms

7561347, DT: 23.1 1.2016) RE-EXPORT Methanesulfonic acid, trifluoro-, anhydride Triflic anhydride solution TRIFLUOROMETHANE SULFONIC ANHYDRIDE(ORIG INAL IMPORT VIDE BE.NO Trifluoromethanesulfonic anhydlladium(0) Trifluoromethanesulfonic anhydride solution Trifluoromethanesulfonic anhydride solution 1 M in methylene chloride

1.3 CAS No.
358-23-6
1.4 CID
67749
1.5 EINECS(EC#)
206-616-8
1.6 Molecular Formula
C2F6O5S2 (isomer)
1.7 Inchi
InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
1.8 InChkey
WJKHJLXJJJATHN-UHFFFAOYSA-N
1.9 Canonical Smiles
C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
1.10 Isomers Smiles
C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
2. Properties
3.1 Density
1.677
3.1 Melting point
-80°C
3.1 Boiling point
80-83℃ (745 mmHg)
3.1 Refractive index
1.32-1.323
3.1 Flash Point
12.3°C
3.1 Vapour pressure
8 mm Hg ( 20 °C)
3.1 Precise Quality
281.90900
3.1 PSA
94.27000
3.1 logP
2.86380
3.1 Solubility
Miscible with dichloromethane. Immiscible with hydrocarbons.
3.2 VaporDensity
5.2 (vs air)
3.3 Appearance
Clear, colorless liquid.
3.4 Chemical Properties
clear colorless to light brown liquid
3.5 Color/Form
Clear colorless to light brown
3.6 Water Solubility
reacts violently with water
3.7 Stability
Stable under normal temperatures and pressures.
3.8 StorageTemp
Refrigerator
3. Use and Manufacturing
4.1 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 Preparation Products
4.2 Storage
Moisture Sensitive. Ambient temperatures.
4.3 Usage
Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.
4. Safety and Handling
5.1 Hazard Codes
C
5.1 Risk Statements
R14;R35
5.1 Safety Statements
S26;S36/37/39;S45;S8
5.1 Packing Group
I
5.1 Hazard Class
8
5.1 RIDADR
UN 3265
5.1 WGK Germany
3
5.1 RTECS
PB2772000
5.1 Sensitive
Moisture Sensitive
5.2 Specification

The Trifluoromethanesulfonic anhydride, with its?CAS registry number 358-23-6, has its IUPAC name of trifluoromethylsulfonyl trifluoromethanesulfonate. For being a kind of clear colorless to light brown liquid, it is sensitive to moisture and it could react violently with water. Besides, its product categories are including pharmacetical; Organic Fluorides. As to its usage, it is known to one of the strongest organic acids, which is widely used in pharmaceutical, chemical and other industries.
?
The physical properties of this chemical are as below: (1)ACD/LogP: 2.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.12; (4)ACD/LogD (pH 7.4): 2.12; (5)ACD/BCF (pH 5.5): 24.01; (6)ACD/BCF (pH 7.4): 24.01; (7)ACD/KOC (pH 5.5): 338.59; (8)ACD/KOC (pH 7.4): 338.59; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 94.27; (13)Index of Refraction: 1.358; (14)Molar Refractivity: 31.41 cm3; (15)Molar Volume: 142.7 cm3; (16)Polarizability: 12.45×10-24 cm3; (17)Surface Tension: 34.1 dyne/cm; (18)Density: 1.976 g/cm3; (19)Enthalpy of Vaporization: 30.98 kJ/mol; (20)Boiling Point: 82.6 °C at 760 mmHg; (21)Vapour Pressure: 86.8 mmHg at 25°C; (22)Exact Mass: 281.909134; (23)MonoIsotopic Mass: 281.909134; (24)Topological Polar Surface Area: 94.3; (25)Heavy Atom Count: 15; (26)Complexity: 370.

Use of this chemical: trifluoro-methanesulfonic acid could react to produce trifluoromethanesulfonic anhydride. This reaction could happen in the presence of the reagent of P2O5.

Production method of this chemical: tetrahydrofuran could react with trifluoromethanesulfonic anhydride to produce 1,4-bis-trifluoromethanesulfonyloxy-butane. This reaction could react in the presence of the solvent of CH2Cl2.

When you are dealing with this chemical, you should be very careful. For being corrosive, this chemical may destroy living tissue on contact and it will be very dangerous if by inhalation and in contact with skin. Besides, it may causes severe burns. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water). And then if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). When you need to store it, keep this container dry.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
(2)InChI: InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
(3)InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N??

5.3 Toxicity
LD50 orally in Rabbit: 1012 mg/kg
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1A

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H314 Causes severe skin burns and eye damage

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
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.
10. Computational chemical data
  • Molecular Weight:282.138819g/mol
  • Molecular Formula:C2F6O5S2
  • Compound Is Canonicalized:True
  • XLogP3-AA:1.6
  • Exact Mass:281.90913442
  • Monoisotopic Mass:281.90913442
  • Complexity:370
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:11
  • Topological Polar Surface Area:94.3
  • Heavy Atom Count:15
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
11. Question & Answer
  • Triflic anhydride is the chemical compound with the formula (CF3SO2)2O. It is the acid anhydride derived from triflic acid. This compound is a particularly strong electrophile, useful for introducing the triflyl group, CF3SO2. Abbreviated Tf2O, triflic anhydride is the acid anhydride of the strong ...
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