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Merck
CN

679674

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
NACRES:
NA.22
PubChem Substance ID:
24885507
UNSPSC Code:
12352005
MDL number:
MFCD09265129

Key Documents

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Product Name

2-Benzyloxy-1-methylpyridinium triflate, 96%

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

SMILES string

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

InChI key

DUXHYQYOPHEFGC-UHFFFAOYSA-M

assay

96%

form

solid

mp

85-91 °C

functional group

fluoro
phenyl
triflate

storage temp.

2-8°C

Quality Level

200

Related Categories

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

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
0000464547
0000464547
0000431148
0000431148
0000160522

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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
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.
Dudley, G. B. et al.
Synlett, 3142-3142 (2005)

Articles

Dudley Reagents

Dudley Reagents provide mild protection for alcohols and carboxylic acids in synthesis.

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