2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate

Name: 2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate
Brand: ChemScene
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CAS No. 59643-43-5
Cat. No. CS-0181794
Purity≥98%
MDL No.MFCD00229854

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Excepted Quantity	$0.00
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2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate|CS-0181794

Structure of 59643-43-5

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General Information

CAS No. 59643-43-5
Cat. No. CS-0181794
Purity ≥98%
MDL No. MFCD00229854
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₃F₃O₄S
Molecular Weight 356.40
Synonym(s) 2,6-Di-tert-butyl-4-methylpyrylium Triflate
SMILES CC1=CC(C(C)(C)C)=[O+]C(C(C)(C)C)=C1.O=S(C(F)(F)F)([O-])=O

Description

This bench-stable pyrylium salt features a sterically shielded core with electron-deficient aromaticity, enabling selective electrophilic functionalization. The trifluoromethanesulfonate counterion ensures high solubility in polar aprotic solvents, facilitating efficient coupling reactions under mild conditions.

Application

2,6-Di-tert-butyl-4-methylpyrylium trifluoromethanesulfonate serves as a highly stable, bench-ready electrophilic alkylating agent that facilitates efficient O- and N-alkylation of enolates and amines under mild conditions. Its steric shielding by tert-butyl groups enhances stability and minimizes side reactions, while the triflate counterion ensures high reactivity and ease of purification. This reagent functions reliably in the synthesis of complex heterocycles and functionalized building blocks for medicinal chemistry applications.

Synthesis

Route1
- 1493-13-6
- 3282-30-2
- ~84%
- In-stock
  
  59643-43-5
References
- Gmelin Handbook: F: PerFHalOrg.SVol.3, 6.2.3.1, page 48 - 120

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

TPSA 68.5
LogP 4.51552
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate

CAS No. 59643-43-5

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