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2-Benzyloxy-1-methylpyridinium triflate

Name: 2-Benzyloxy-1-methylpyridinium triflate
Brand: ALDRICH

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

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

GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Precautionary Statements

P261 - P264 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

G4251

L-Glutathione reduced

Mix-and-heat benzylation of alcohols using a bench-stable pyridinium salt.

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.

Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate.

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.