882980-43-0

Basic information

• Product Name: Bn-OPT, Dudley Reagent
• Synonyms: 2-Benzyloxy-1-methylpyridinium triflate;Bn-OPT, Dudley Reagent;2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate;1-Methyl-2-(phenylmethoxy)-pyridinium 1,1,1-trifluoromethanesulfonate;Dudley's reagent;Bn-OPT;2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate (This product is only available in Japan.);2-Benzyloxy-1-methylpyridinium triflate 96%
• CAS NO: 882980-43-0
• Molecular Formula: C14H14F3NO4S
• Molecular Weight: 0
• Mol File: 882980-43-0.mol

Chemical Properties

• Melting Point: 85-91 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Bn-OPT, Dudley Reagent(CAS DataBase Reference)
• NIST Chemistry Reference: Bn-OPT, Dudley Reagent(882980-43-0)
• EPA Substance Registry System: Bn-OPT, Dudley Reagent(882980-43-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 882980-43-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Bn-OPT, Dudley Reagent is used as a protecting group for alcohols during organic synthesis for the following reasons:
1. It allows for selective protection of alcohols without affecting other functional groups present in the molecule.
2. The neutral conditions provided by the reagent prevent unwanted side reactions and degradation of sensitive functional groups.
3. The benzyl ester formed is stable and can be easily removed under mild conditions, ensuring the integrity of the final product.
Used in Pharmaceutical Industry:
Bn-OPT, Dudley Reagent is used as a key intermediate in the synthesis of pharmaceutical compounds for the following reasons:
1. Its ability to selectively protect alcohols enables the synthesis of complex molecules with multiple functional groups.
2. The mild conditions required for the formation and removal of the benzyl ester protect the integrity of the pharmaceutical compounds, ensuring their stability and efficacy.
3. The reagent's compatibility with a wide range of substrates allows for the development of diverse drug candidates with potential therapeutic applications.
Used in Chemical Research:
Bn-OPT, Dudley Reagent is used as a research tool in chemical laboratories for the following reasons:
1. It provides a means to study the reactivity and selectivity of alcohols in various chemical reactions.
2. The reagent's ability to form stable benzyl esters allows researchers to investigate the properties and behavior of these esters in different chemical environments.
3. The mild conditions and compatibility with a wide range of substrates make it suitable for exploring new synthetic routes and methodologies in chemical research.

InChI:InChI=1/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

Upstream product

• 100-51-6 benzyl alcohol 
• 109-09-1 2-chloropyridine 
• 40864-08-2 2-benzyloxypyridine 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 32565-76-7 (2,6-dimethyloxy-4-methyl)phenyl 
• 32565-33-6 1-benzyl-2,4-dimethoxybenzene 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 23450-18-2 2-benzyl-1-bromobenzene 
• 1417721-70-0 C₆₈H₇₄N₆O₁₃ 
• 1394226-64-2 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 

Relevant articles and documents

3BéTA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERS

The present invention generally relates to a specific pregnenolone derivative for its use for the treatment of a cognitive disorders. More particularly, the invention relates to a compound of Formula (I) for its use in the treatment of cognitive disorders. Indeed, the compound of the invention is in vivo very potent in correcting the cognitive impairments observed in cognitive disorders.

New reagents for the synthesis of arylmethyl ethers and esters

This Account chronicles efforts leading up to the development of new arylmethyl transfer (benzylation) reagents for protecting oxygen functional groups under relatively mild and neutral conditions. It begins with an investigation of organosiletanes as surrogate hydroxyl groups, which inspired siletane-functionalized benzyl ethers and forced us to confront the difficulties associated with the synthesis of benzyl ethers. The end result is a new series of neutral oxypyridinium salts for the benzylation of various nucleophilic functional groups under mild conditions. 1 Introduction 2 Tamao-type Oxidation of Strained Organosiletanes 3 p-Siletanylbenzyl (PSB) Protecting Groups 4 2-Benzyloxy-1-methylpyridinium Triflate 5 Friedel-Crafts Reactions and Mechanistic Insights 6 Benzyl Ester Formation 7 Substituted Benzyl Transfer Reagents 8 Conclusions and Outlook. Georg Thieme Verlag Stuttgart New York.

Compounds and methods of arylmethylation (benzylation) as protection for alcohol groups during chemical synthesis

A process for benzylating an alcohol includes mixing 2-benzyloxy-1-methylpyridinium triflate in an aromatic hydrocarbon solvent having a predetermined boiling point; adding an acid scavenger to the mixture; combining the alcohol to be benzylated with the mixture; reacting the alcohol with the 2-benzyloxy-1-methylpyridinium triflate by heating above ambient temperature to generate the benzylated alcohol; and separating the benzylated alcohol from the mixture.

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

2-Benzyloxy-1-methylpyridinium inflate (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.

A bench-stable organic salt for the benzylation of alcohols

2-Benzyloxy-1-methylpyridinium inflate (Bn-OPT) effects the benzylation of alcohols in the absence of acidic or basic promoters. Solutions of Bn-OPT and primary, secondary, or tertiary alcohols give rise to the corresponding benzyl ethers upon mild heating. Acid scavengers are generally included in the reaction mixture. Bn-OPT is crystalline and bench-stable. Georg Thieme Verlag Stuttgart.