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679674

Sigma-Aldrich

2-Benzyloxy-1-methylpyridinium triflate

96%

Synonym(s):

Bn-OPT, Dudley Reagent

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About This Item

Empirical Formula (Hill Notation):
C14H14F3NO4S
CAS Number:
882980-43-0
Molecular Weight:
349.33
MDL number:
MFCD09265129
UNSPSC Code:
12352005
PubChem Substance ID:
24885507
NACRES:
NA.22

assay

96%

form

solid

mp

85-91 °C

functional group

fluoro
phenyl
triflate

storage temp.

2-8°C

SMILES string

[O-]S(=O)(=O)C(F)(F)F.C[n+]1ccccc1OCc2ccccc2

InChI

1S/C13H14NO.CHF3O3S/c1-14-10-6-5-9-13(14)15-11-12-7-3-2-4-8-12;2-1(3,4)8(5,6)7/h2-10H,11H2,1H3;(H,5,6,7)/q+1;/p-1

InChI key

DUXHYQYOPHEFGC-UHFFFAOYSA-M

Application

Dudley Reagents


  • Novel reagent for benzyl protection of alcohols under neutral conditions. Promotes selective formation of benzyl esters of carboxylic acids in presence of triethylamine.

Legal Information

Sold under license from FSURF, US patent 7,754,909 and related patents apply. Label license, without restriction to scale, is granted to end-user upon purchase.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC3237V
BGBB4530V
09229AH

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Kevin W C Poon et al.
The Journal of organic chemistry, 71(10), 3923-3927 (2006-05-06)
2-Benzyloxy-1-methylpyridinium triflate (1) is a stable, neutral organic salt that converts alcohols into benzyl ethers upon warming. The synthesis and reactivity of 1 are described herein. Benzylation of a wide range of alcohols occurs in good to excellent yield.
Jumreang Tummatorn et al.
The Journal of organic chemistry, 72(23), 8962-8964 (2007-10-16)
Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained
Dudley, G. B. et al.
Synlett, 3142-3142 (2005)

Articles

Dudley Benzylation Reagent

Benzyl ethers and derivatives are among the most widely used protecting groups in organic synthesis. Cleavage can be effected under a variety of conditions including hydrogenolysis, oxidation, and acid decomposition.

Dudley Reagents

Benzyl and p-methoxy benzyl protecting groups require use of acidic or basic reaction media and/or otherwise non-mild reaction conditions, which sometimes are not compatible with other functional groups in the molecule. Dudley Reagents provide protection of alcohols and carboxylic acids under relatively neutral reaction conditions

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