317-55-5

Basic information

• Product Name: 1-Naphthalenesulfonyl fluoride
• CAS NO: 317-55-5
• Molecular Formula: C10H7FO2S
• Molecular Weight: 210.229
• Mol File: 317-55-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenesulfonyl fluoride(317-55-5)
• EPA Substance Registry System: 1-Naphthalenesulfonyl fluoride(317-55-5)

Safety Data

• Hazardous Substances Data: 317-55-5(Hazardous Substances Data)

Usage

Physical appearance

A white to light brown solid, which describes the compound's color and texture.

Solubility

Insoluble in water, which indicates that the compound does not dissolve well in aqueous solutions.

Biological activity

A potent inhibitor of serine proteases, which are enzymes that play a key role in many biological processes. This property makes 1-Naphthalenesulfonyl fluoride useful in the synthesis of pharmaceutical drugs and other organic compounds.

Mechanism of action

Reacts with the hydroxyl groups of serine residues in proteins, irreversibly inhibiting their activity. This describes how the compound interacts with its target enzymes and exerts its inhibitory effects.

Applications

Used in the fields of biochemistry, molecular biology, and pharmaceutical research, which indicates the broad range of scientific disciplines in which 1-Naphthalenesulfonyl fluoride is useful.

Safety concerns

Highly toxic and can cause severe skin and eye irritation, which highlights the need for careful handling and appropriate safety precautions when working with this compound.

Upstream product

• 91-20-3 naphthalene 
• 7789-21-1 fluorosulphonic acid 
• 130-14-3 sodium 1-naphthalenesulfonate 
• 2243-56-3 1-naphthylhydrazine hydrochloride 
• 13922-41-3 1-Naphthylboronic acid 
• 28912-93-8 1-naphthyldiazonium tetrafluoroborate 
• 134-32-7 1-amino-naphthalene 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 90-14-2 1-Iodonaphthalene 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 92964-93-7 1-naphthalenesulfonic acid phenyl ester 

Relevant articles and documents

Facile one-pot synthesis of sulfonyl fluorides from sulfonates or sulfonic acids

A facile cascade process for directly transforming the abundant and inexpensive sulfonates (or sulfonic acids) to the highly valuable sulfonyl fluorides was developed. This new protocol features mild reaction conditions using readily available and easy-to-operate reagents. A diverse set of sulfonyl fluorides was prepared facilitating the enrichment of the sulfonyl fluoride library.

Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange-based “click chemistry.” Herein, a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K2S2O5 and N-fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible-light-mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. (Figure presented.).

Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source andN-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.