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679674

Sigma-Aldrich

2-Benzyloxy-1-methylpyridinium triflate

96%

Synonym(s):

Bn-OPT, Dudley Reagent

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$185.00
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$237.00

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1 G
$185.00
5 G
$237.00

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
form:
solid
assay:
96%

$185.00

In StockDetails

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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.[1][2] Promotes selective formation of benzyl esters of carboxylic acids in presence of triethylamine.[3]

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 Reagents

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

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