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176176

Trifluoromethanesulfonic anhydride

99%

Trifluoromethanesulfonic anhydride

Synonym(s):

Triflic anhydride

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5 g
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$60.60
10 g
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$80.10
50 g
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$247.00
250 g

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500 g
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$2,130.00

About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
Molecular Weight:
282.14
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-616-8
Beilstein/REAXYS Number:
1813600
MDL number:
Assay:
99%
Form:
liquid

$60.60


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vapor density

5.2 (vs air)

Quality Segment

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

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.

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.
  • 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.
  • A reagent to prepare substituted tetrazoles from secondary amides using sodium azide.
  • A reagent in Bischler−Napieraiski cyclization reaction along with 4-(N,N-dimethylamnino)pyridine.

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This Item
91737164798143502
assay

99%

assay

≥98.0% (T)

assay

≥99%

assay

99%

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

density

1.677 g/mL at 25 °C (lit.)

density

1.677 g/mL at 25 °C (lit.)

density

1.583 g/mL at 25 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

bp

81-83 °C (lit.)

bp

81-83 °C (lit.)

bp

29-32 °C (lit.)

bp

193 °C (lit.)

refractive index

n20/D 1.321 (lit.)

refractive index

n20/D 1.321 (lit.)

refractive index

n20/D 1.334 (lit.)

refractive index

n20/D 1.409 (lit.)

form

liquid

form

liquid

form

liquid

form

liquid


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signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

5.1B - Oxidizing hazardous materials

wgk

WGK 3

flash_point_f

not determinedboils before flash

flash_point_c

not determinedboils before flash

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter



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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)
Chimica Oggi, 22, 48-48 (2004)
[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)



Global Trade Item Number

SKUGTIN
176176-500G04061833544822
176176-4KG04061833688458
176176-250G04061838752789
176176-5G04061838752802
176176-1KG04061838752772
176176-10G04061838752765
176176-PZ04061823818766
176176-50G04061838752796

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/418/501/product-dating-information-06-25-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

      Helpful?

Reviews

Active Filters

    • Review 1
    • Votes 22
    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.