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176176

Sigma-Aldrich

Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride

99%

Synonym(s):

Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
358-23-6
Molecular Weight:
282.14
Beilstein:
1813600
EC Number:
206-616-8
MDL number:
MFCD00000408
UNSPSC Code:
12352101
PubChem Substance ID:
24850557
NACRES:
NA.22
form:
liquid
Assay:
99%
Pricing and availability is not currently available.

vapor density

5.2 (vs air)

Quality Level

200

vapor pressure

8 mmHg ( 20 °C)

Assay

99%

form

liquid

refractive index

n20/D 1.321 (lit.)

bp

81-83 °C (lit.)

density

1.677 g/mL at 25 °C (lit.)

functional group

fluoro
triflate

SMILES string

FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F

InChI

1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8

InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

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General description

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is an electrophilic reagent that is an efficient source of trifluoromethyl. It is commonly used in organic chemistry to convert oxygen-containing compounds to triflates and for the electrophilic activation and subsequent conversion of amides, sulfoxides, and phosphorus oxides. [1]

Application

Catalyst for glycosylation for synthesis of polysaccharides

Reagent for stereoselective synthesis of mannosazide methyl uronate donors

Activator for direct glycosylation with anomeric hydroxy sugars
Trifluoromethanesulfonic anhydride can be used as :
  • A Reactant in the synthesis of Dipentaerythritol hexatriflate via triflatation method and Azido-diphenyl-acetic acid.[2]
  • Catalyst for glycosylation for synthesis of polysaccharides.
  • Reagent for stereoselective synthesis of mannosazide methyl uronate donors.
  • Activator for direct glycosylation with anomeric hydroxy sugars
  • A methylation reagent to synthesize trifluoromethylated compounds by direct introduction of CF3 group to (hetero)arenes.[3]
  • A reagent to prepare substituted tetrazoles from secondary amides using sodium azide.[4]
  • A reagent in Bischler−Napieraiski cyclization reaction along with 4-(N,N-dimethylamnino)pyridine.[5]

Signal Word

Danger

Hazard Statements

H272,H302,H314,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Ox. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Flash Point(F)

not determinedboils before flash

Flash Point(C)

not determinedboils before flash

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR2196
MKCW3664
0000227233
0000227233
BCCJ7858

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Chimica Oggi, 22, 48-48 (2004)
Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
Ouyang Y, et al.
Angewandte Chemie (International Edition in English), 57(23), 6926-6929 (2018)
Trifluoromethanesulfonic anhydride-4-(N, N-dimethylamino) pyridine as a reagent combination for effecting Bischler-Napieraiski cyclisation under mild conditions: application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine
David CR, et al.
Journal of the Chemical Society. Chemical Communications, 1993(24), 2551-2553 (1995)
[11 C] phenytoin revisited: synthesis by [11 C] CO carbonylation and first evaluation as a P-gp tracer in rats
Joost V,et al.
EJNMMI Research, 2, 1-11 (2012)
Controlled star poly (2-oxazoline) s: Synthesis, characterization
Laetitia P,et al.
European Polymer Journal, 122, 109323-109323 (2020)
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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Reviews

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    • Review 1
    • Votes 17
    2 out of 5 stars.

    Disappointed in packaging

    This triflic anhydride appeared to be good quality when received, however I am very disappointed with its packaging. A chemical this water-sensitive really needs to be packaged with an Aldrich Sure/Seal septum cap in my opinion. This bottle simply has an ordinary screw cap, making it very difficult to keep dry and even dangerous to handle (it fumes aggressively). As packaged, this expensive chemical cannot be used without rapidly deteriorating in quality.

    Helpful?

    1. Response from MilliporeSigma:

      176176 is moisture sensitive and is packaged under inert gas. When handling these moisture sensitive products we recommend flushing the bottle with nitrogen between uses, limiting exposure to atmosphere, and keeping the inside of the cap/opening of the bottle clean. Customers may want to consider ordering multiple bottles of smaller pack sizes to limit the number of times the bottle is opened. Your feedback has been shared with the product manager, they will review the packaging specifications and make changes as necessary.

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