455-26-5

Basic information

• Product Name: 4-(FLUOROSULFONYL)BENZOIC ACID
• Synonyms: 4-(FLUOROSULFONYL)BENZOIC ACID;4-(fluorosulphonyl)benzoic acid
• CAS NO: 455-26-5
• Molecular Formula: C₇H₅FO₄S
• Molecular Weight: 204.18
• EINECS: 207-243-3
• Product Categories: Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Sulfonyl Fluorides;Sulfonyl Halides;Sulfur Compounds
• Mol File: 455-26-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 272-273 °C(lit.)
• Boiling Point: 335.3°Cat760mmHg
• Flash Point: 156.6°C
• Appearance: /
• Density: 1.538g/cm³
• Vapor Pressure: 4.75E-05mmHg at 25°C
• Refractive Index: 1.545
• PKA: 3.29±0.10(Predicted)
• CAS DataBase Reference: 4-(FLUOROSULFONYL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(FLUOROSULFONYL)BENZOIC ACID(455-26-5)
• EPA Substance Registry System: 4-(FLUOROSULFONYL)BENZOIC ACID(455-26-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 455-26-5(Hazardous Substances Data)

Usage

Description

4-(Fluorosulfonyl)benzoic acid is a xenobiotic substrate analogue that exhibits unique properties when interacting with specific enzymes, such as the 4-4 isozyme of rat liver glutathione S-transferase. This interaction leads to a time-dependent inactivation of the enzyme, making it a valuable compound for studying enzyme mechanisms and functions.

Uses

Used in Enzyme Research:
4-(Fluorosulfonyl)benzoic acid is used as an affinity label for the dimeric pig lung pi class glutathione S-transferase. Its application in this field is crucial for understanding the structure, function, and regulation of glutathione S-transferases, which play a significant role in detoxification processes and cellular defense mechanisms.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Fluorosulfonyl)benzoic acid serves as a valuable tool for the development of new drugs and therapies. Its ability to inactivate specific enzymes can be harnessed to design drugs that target and modulate the activity of these enzymes, potentially leading to novel treatments for various diseases and conditions.
Used in Chemical Synthesis:
4-(Fluorosulfonyl)benzoic acid can also be utilized in chemical synthesis as a building block or intermediate for the development of new compounds with diverse applications. Its unique structure and reactivity make it a promising candidate for the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C7H5FO4S/c8-13(11,12)6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

Upstream product

• 7516-60-1 4-chlorosulfonylbenzoyl chloride 
• 10130-89-9 p-carboxyphenylsulfonyl chloride 
• 65-85-0 benzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 5399-63-3 potassium p-carboxybenzenesulfonate 

Downstream Products

• 402-55-1 4-fluorosulfonylbenzoyl chloride 
• 124397-38-2 4-methoxycarbonylbenzenesulphonyl fluoride 
• 366-85-8 4-(ethoxycarbonyl)-benzenesulfonyl fluoride 
• 57-66-9 4-[(dipropylamino)sulfonyl]benzoic acid 
• 57454-44-1 5'-FSBA 

Relevant articles and documents

Chemoselective reaction of bifunctional carboxysulfonic acid systems: Preparation of useful intermediates for chemiluminescent, fluorescent and UV absorbing bifunctional linkers

Heterobifunctional compounds are of considerable interest in convergent synthesis strategies as well as in the labeling/tagging of biological molecules. Herein is described a synthetic strategy to functionalize sulfonic acids in the presence of carboxylic acids without the need for protection/deprotection steps. Bifunctional carboxysulfonic acids are transformed under mild conditions to the corresponding carboxysulfonyl fluorides which are reacted with the amine of choice to provide sulfonamides. The carboxylic acid remains free and is available for subsequent activation and further chemical elaboration. The generality of this approach is demonstrated herein, and an example of utility is outlined in which carboxysulfonyl-containing chemiluminescent reagents are transformed into unique red-shifted chemiluminescent reagents.

Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides

A copper-free Sandmeyer-type fluorosulfonylation reaction is reported. Utilizing Na2S2O5 and Selectfluor as the sulfur dioxide and fluorine sources, respectively, aryldiazonium salts were transformed into sulfonyl fluorides. The one-pot direct synthesis of sulfonyl fluorides from aromatic amines was also realized via in situ diazotization. The practicality of this method was demonstrated by the broad functional group tolerance, gram-scale synthesis, and late-stage fluorosulfonylation of natural products and pharmaceuticals.

Sulfur(VI) fluoride compounds and methods for the preparation thereof

This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.