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CAS RN: 358-23-6 | Product Number: T1100

Trifluoromethanesulfonic Anhydride


Purity: >98.0%(T)
Synonyms:
Documents:
10G
$54.00
32   4   ≥100 
25G
$91.00
16   Contact Us ≥100 
250G
$453.00
3   15   ≥100 

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Product Number T1100
Purity / Analysis Method >98.0%(T)
Molecular Formula / Molecular Weight C__2F__6O__5S__2 = 282.13 
Physical State (20 deg.C) Liquid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive,Heat Sensitive
CAS RN 358-23-6
Reaxys Registry Number 1813600
PubChem Substance ID 87576894
SDBS (AIST Spectral DB) 13774
MDL Number

MFCD00000408

Specifications
Appearance Colorless to Almost colorless clear liquid
Purity(Neutralization titration) min. 98.0 %
Properties (reference)
Melting Point -80 °C
Boiling Point 84 °C
Specific Gravity (20/20) 1.72
Refractive Index 1.32
GHS
Pictogram Pictogram
Signal Word Danger
Hazard Statements H314 : Causes severe skin burns and eye damage.
H290 : May be corrosive to metals.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P234 : Keep only in original container.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P390 : Absorb spillage to prevent material damage.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P406 : Store in corrosive resistant container with a resistant inner liner.
P405 : Store locked up.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN3265
Class (DOT-AIR) 8
Packing Group (TCI-A) II
HS Number 2904.10.5000
Application
TCI Practical Example: Dehydration of a Carbamoyl Group Using Tf2O

TCI Practical Example: Dehydration of a Carbamoyl Group Using Tf2O

Used Chemicals

Procedure

Tf2O (0.32 mL, 2.0 mmol, 1.3 eq.) was slowly added to a solution of 4-bromobenzamide (300 mg, 1.5 mmol), and triethylamine (0.54 mL, 3.9 mmol, 2.6 eq.) in dichloromethane (3 mL) at 0 °C. The mixture was stirred at room temperature for 2 hours. Then additional triethylamine (1.1 mL, 7.8 mmol, 5.2 eq.) and Tf2O (0.64 mL, 3.9 mmol, 2.6 eq.) were added at 0 °C and the mixture was stirred at r.t. for overnight. The reaction mixture was quenched with water (15 mL) and the aqueous layer was extracted with ethyl acetate (15 mL x 3). The combined organic layer was washed with 2 mol/L HCl aq. (15 mL), sat. NaHCO3 aq. (15 mL), and brine (15 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, ethyl acetate:hexane = 1:8) to give 4-bromobenzonitrile a pale yellow solid (165 mg, 61% yield).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.

Analytical Data

4-bromobenzonitrile

1H NMR (400 MHz, CDCl3); δ 7.64 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 8.4 Hz, 2H).

Lead Reference


Application
Transformation of Aliphatic and Aromatic Secondary Amides to Nitriles

Typical Procedure:
To an ice bath-cooled solution of a secondary amide (1.0 mmol) and 2-fluoropyridine (1.2 mmol) in anhydrous CH2Cl2 (5 mL) is added Tf2O (1.1 mmol). After being stirred for 0.5 h, the reaction mixture is warmed to 30 °C and stirred until completion of the reaction (monitored by TLC analysis). The reaction is quenched with 1 M HCl (1.0 mL), and the mixture is extracted with CH2Cl2 (3×10 mL). The combined organic layers are washed with saturated sodium carbonate (5 mL) and brine (5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (ethyl acetate/petroleum ether) to afford the corresponding nitrile.

References


Application
Enol Triflate

References


PubMed Literature


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