368-88-7

Basic information

• Product Name: 4-FLUOROBENZENESULFONIC ACID
• Synonyms: 4-FLUOROBENZENESULFONIC ACID;4-fluorobenzenesulphonic acid;Benzene-1-fluoro-4-sulfonic acid;NSC43021;p-Fluorobenzenesulfonic acid;p-Fluorophenylsulfonic acid
• CAS NO: 368-88-7
• Molecular Formula: C₆H₅FO₃S
• Molecular Weight: 176.17
• EINECS: 206-714-0
• Mol File: 368-88-7.mol

Chemical Properties

• Melting Point: 87℃
• Appearance: /
• Density: 1.513
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.66±0.50(Predicted)
• Water Solubility: 434.9g/L(21.3 oC)
• CAS DataBase Reference: 4-FLUOROBENZENESULFONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROBENZENESULFONIC ACID(368-88-7)
• EPA Substance Registry System: 4-FLUOROBENZENESULFONIC ACID(368-88-7)

Safety Data

• Hazardous Substances Data: 368-88-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorobenzenesulfonic Acid is used as a reactant in the synthesis of HCV (Hepatitis C Virus) inhibitors based on the thiazolone scaffold. Its strong acidic nature and the presence of the fluorine atom make it a valuable component in the development of new antiviral drugs, particularly those targeting HCV.
In the synthesis process, 4-Fluorobenzenesulfonic Acid can act as a catalyst or a reagent, facilitating the formation of the desired thiazolone-based HCV inhibitors. These inhibitors can potentially disrupt the viral replication process, thereby helping to control and treat Hepatitis C infections.
The use of 4-Fluorobenzenesulfonic Acid in the pharmaceutical industry highlights its importance in the development of novel therapeutic agents for the treatment of viral diseases. Its unique properties and reactivity make it a promising candidate for further research and application in the field of medicinal chemistry.

InChI:InChI=1/C6H5FO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,(H,8,9,10)

Upstream product

• 462-06-6 fluorobenzene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 405-31-2 bis(4-fluorophenyl)disulfide 
• 371-42-6 4-Fluorothiophenol 
• 305-80-6 4-diazobenzenesulfonic acid 
• 7664-93-9 sulfuric acid 
• 125568-47-0 4-fluorobenzenesulfinic acid ethyl ester 
• 657-47-6 Fluorbenzol-3-sulfonsaeure 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 

Downstream Products

• 462-06-6 fluorobenzene 
• 657-47-6 Fluorbenzol-3-sulfonsaeure 
• 35300-35-7 2-fluorobenzenesulfonic acid 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 216983-39-0 1-((4-fluorophenyl)sulfonyl)piperidin-4-one 
• 2797-28-6 lithium tetrakis(pentafluorophenyl)borate 
• 1637586-78-7 4-((1-((4-fluorophenyl)sulfonyl)piperidin-4-yl)oxy)aniline 
• 1637586-82-3 1-ethyl-3-(4-((1-((4-fluorophenyl)sulfonyl)piperidin-4-yl)oxy)phenyl)urea 
• 1637586-76-5 C₁₇H₁₇FN₂O₅S 
• 371-42-6 4-Fluorothiophenol 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 

Relevant articles and documents

Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.

Aryl and alkyl sulfonic acid compounds as well as construction method adopting inorganic sulfur salt and application

The invention discloses aryl and alkyl sulfonic acid compounds as shown in a formula (1) and a synthesis method thereof. The method comprises the following step: aromatic iodine and an inorganic sulfur source or alkyl bromide and an inorganic sulfur source as reaction raw materials react in a solvent under the action of alkali, a catalyst or an additive to obtain a series of aryl and alkyl sulfonic acid compounds. According to the method, the aryl and alkyl sulfonic acid compounds are constructed in one step by taking an inorganic sulfur reagent as a sulfur source, so that the defect of the mode in which the aryl and alkyl sulfonic acid compounds are synthesized by taking concentrated sulfuric acid, chlorosulfonic acid or sulfur dioxide gas and the like as sulfonating reagents in the priorart is avoided. The aryl and alkyl sulfonic acid compounds developed by the invention can be used for synthesizing aryl and alkyl sulfonic acid drug analogues.

Sustainable access to sulfonic acids from halides and thiourea dioxide with air

A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.

Preparation method of vonoprazan fumarate and intermediate thereof

The invention discloses a preparation method of vonoprazan fumarate. The method comprises the steps that R1) a compound of formula I is subjected to sulfonation to obtain a compound of formula II; R2)the compound of the formula II is dissolved in a solven

Bromotrifluoromethoxy compound and synthetic method thereof

According to the invention, a series of trifluoromethoxy reagent precursors are synthesized, and trifluoromethoxy silver with high activity can be obtained under the condition of an activating reagent. By the utilization of the idea, a bromotrifluorometho

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles

H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.

Synthesis of symmetrical triarylphosphines from aryl fluorides and red phosphorus: Scope and limitations

The reaction of aryl fluorides with phosphide anion, generated in situ from the reduction of red phosphorus by lithium metal in liquid ammonia, gave symmetrical triarylphosphines in fair to good yields. Phosphonodiamide, sulfonamide, 2-oxazolyl, and nitrile groups were stable to the reaction conditions, while nitro and bromo substituents were not. para-Substituted aryl fluorides gave higher yields than meta-substituted aryl fluorides, and ortho-substituted aryl fluorides failed to react.

Wasserloesliche Phosphane. II. Ein neuer Syntheseweg fuer wasserloesliche sekundaere und tertiaere Phosphane mit sulfonierten aromatischen Resten - Kristallstruktur von P(p-C6H4-SO3K)3*KCl*0.5H2O

Water soluble tertiary phosphanes 2, 7, 10-17 with sulfonated aromatic substituents p-C6H4-SO3K and 2,4-C6H3(SO3K)2 can be obtained in good yields by nucleophilic aromatic substitution of fluorine in p-F-C6H4-SO3K (1) or F-C6H3-2,4-(SO3K)2 (5) with PH3 or primary and secondary phosphanes in the superbasic medium dimethyl sulfoxide (DMSO)/KOH(solid).The first water-soluble secondary phosphane HP2 (6) having sulfonated aromatic substituents can be obtained if 5 is reacted under similar conditions with PH3.Highly sulfonated phosphanes (7-9) with remarkable solubilities in water are formed upon reaction of 6 with F-C6H5, n-BuBr or C6H5-CH2-Br, respectively, in the superbasic medium.The resulting compounds have been identified by their 1H, 13C and 31P NMR spectra.X-Ray structural analysis of P(p-C6H4-SO3K)3*KCl*0.5H2O shows C3 symmetry for the trianion of 2 with the P-C-P bond angles (103.5(2)o) and P-C bond lengths (1.843(4) Angstroem) being almost identical to those in Ph3P.Key words: Phosphine; Catalysis; Nuclear magnetic resonance; Water soluble phosphine; Phase transfer; Hydroformylation