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424102

Sigma-Aldrich

4-Nitrophenyl trifluoromethanesulfonate

99%

Synonym(s):

4-Nitrophenyl triflate

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About This Item

Linear Formula:
CF3SO3C6H4NO2
CAS Number:
17763-80-3
Molecular Weight:
271.17
MDL number:
MFCD00192354
UNSPSC Code:
12352100
PubChem Substance ID:
24866551

Assay

99%

form

solid

mp

52-55 °C (lit.)

functional group

fluoro
nitro
triflate

SMILES string

[O-][N+](=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1

InChI

1S/C7H4F3NO5S/c8-7(9,10)17(14,15)16-6-3-1-5(2-4-6)11(12)13/h1-4H

InChI key

NDTIXHNCNLKURN-UHFFFAOYSA-N

Application

4-Nitrophenyl trifluoromethanesulfonate (4-nitrophenyltriflate) may be used in the following studies:
  • As a triflating agent in the synthesis of aryl triflates.[1]
  • As a reagent in the synthesis of aryl nonaflate.[2]
  • As a reagent for palladium catalyzed coupling reactions with different substrates.[3][4]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Precautionary Statements

P280 - P305 + P351 + P338 - P310

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
18696TMV
18696TM
13227LH
16321MS
00314HG

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Trifluoromethanesulfonic anhydride 99%

Sigma-Aldrich

176176

Trifluoromethanesulfonic anhydride

Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates.
Ohe T, et al.
The Journal of Organic Chemistry, 58(8), 2201-2208 (1993)
Regioselective palladium-catalyzed arylation of vinyl ethers with 4-nitrophenyl triflate. Control by addition of halide ions.
Andersson CM and Hallberg A.
The Journal of Organic Chemistry, 53(9), 2112-2114 (1988)
A high throughput synthesis of aryl triflate and aryl nonaflate promoted by a polymer supported base (PTBD).
Boisnard S, et al.
Tetrahedron Letters, 40(42), 7469-7472 (1999)
4-Nitrophenyltriflate as a new triflating agent.
Zhu J, et al.
Tetrahedron Letters, 38(7), 1181-1182 (1997)

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