133042-64-5

Basic information

• Product Name: 1-<(Fluorosulfonyl)oxy>naphthalene
• Synonyms: 1-<(Fluorosulfonyl)oxy>naphthalene
• CAS NO: 133042-64-5
• Molecular Weight: 226.228
• Mol File: 133042-64-5.mol
• Article Data: 8

Chemical Properties

• Density: 1.3674 g/mL at 25 °C
• Refractive Index: n20/D 1.5576
• CAS DataBase Reference: 1-<(Fluorosulfonyl)oxy>naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<(Fluorosulfonyl)oxy>naphthalene(133042-64-5)
• EPA Substance Registry System: 1-<(Fluorosulfonyl)oxy>naphthalene(133042-64-5)

Safety Data

• Hazardous Substances Data: 133042-64-5(Hazardous Substances Data)

Usage

Uses

The following aryl fluorosulfate can be utilized as a cross-coupling partner in Suzuki-Miyaura reactions. The standard reaction conditions for these palladium-catalyzed C-C bond formations are ligand-free and can be performed in water, at room temperature and are not air sensitive.

Upstream product

• 1139705-28-4 naphthalene-1-yl 1H-imidazole-1-sulfonate 
• 640723-20-2 fluorosulfonyl fluoride 
• 90-15-3 α-naphthol 

Downstream Products

• 3095-33-8 (naphthalen-1-yl)diphenylphosphine oxide 
• 86-55-5 1-naphthalenecarboxylic acid 
• 3007-97-4 ethyl 1-naphthoate 
• 321-38-0 1-Fluoronaphthalene 
• 27331-33-5 1-(4-methoxyphenyl)naphthalene 
• 826-74-4 1-vinylnaphthalene 

Relevant articles and documents

Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies

A series of aryl fluorosulfate analogues (1–37) were synthesized and tested for in vitro antibacterial and antifungal studies, and validated by docking studies. The compounds 9, 12, 14, 19, 25, 26, 35, 36 and 37 exhibited superior antibacterial potency ag

Synthesis of 18F-Labeled Aryl Fluorosulfates via Nucleophilic Radiofluorination

Sulfuryl fluoride gas is a key reagent for SO2F transfer. However, conventional SO2F transfer reactions have limited 18F-radiochemistry translation, due to the inaccessibility of gaseous [18F]SO2F2. Herein, we report the first SO2F2-free synthesis of aryl [18F]fluorosulfates from both phenolic and isolated aryl imidazylate precursors with cyclotron-produced 18F-. The radiochemical yields ranged from moderate to good with excellent functional group tolerance. The reliability of our approach was validated by the automated radiosynthesis of 4-acetamidophenyl [18F]fluorosulfate.

Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates

This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.