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679674

Sigma-Aldrich

2-Benzyloxy-1-methylpyridinium triflate

96%

Synonym(s):

Bn-OPT, Dudley Reagent

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1 G
¥12,800
5 G
¥43,700

¥12,800

Available to ship onApril 11, 2025Details

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1 G
¥12,800
5 G
¥43,700

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

¥12,800

Available to ship onApril 11, 2025Details

Request a Bulk Order

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

Related Categories

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

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

679674-5G:
679674-1G:
679674-VAR:
679674-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000431148
0000431148
0000160522
0000160522
0000160783

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

Articles

Dudley Reagents

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

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