793-75-9

Basic information

• Product Name: phenyl pentafluorobenzenesulfonate
• CAS NO: 793-75-9
• Molecular Formula: C₁₂H₅F₅O₃S
• Molecular Weight: 324.2233
• Mol File: 793-75-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 362°C at 760 mmHg
• Flash Point: 172.7°C
• Density: 1.588g/cm³
• Vapor Pressure: 4.15E-05mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: phenyl pentafluorobenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl pentafluorobenzenesulfonate(793-75-9)
• EPA Substance Registry System: phenyl pentafluorobenzenesulfonate(793-75-9)

Safety Data

• Hazardous Substances Data: 793-75-9(Hazardous Substances Data)

Usage

General Description

Phenyl pentafluorobenzenesulfonate is a chemical compound that consists of a phenyl group attached to a sulfonate group and five fluorine atoms on the benzene ring. It is commonly used as a reagent in organic synthesis for the introduction of phenylsulfonate groups onto various substrates. The pentafluorobenzenesulfonate moiety enhances the reactivity of the compound, making it a valuable tool in the modification of organic molecules. Phenyl pentafluorobenzenesulfonate is known for its high stability and solubility in common organic solvents, making it a versatile and widely used reagent in various chemical reactions.

Upstream product

• 832-53-1 pentafluorobenzenesulonyl chloride 
• 108-95-2 phenol 
• 36650-04-1 pentafluorobenzensulfonyl fluoride 

Downstream Products

• 100-47-0 benzonitrile 

Relevant articles and documents

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

Pentafluorobenzenesulfonamides and analogs

The invention provides methods and compositions relating to novel pentafluorophenylsulfonamide derivatives and analogs and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, vascular restenosis, microbial infections, and psoriasis, or as lead compounds for the development of such agents. The compositions include compounds of the general formula I:

STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG.61. Chemische Reaktivitaet und Halbstufenpotential Vergleichende Versuche am Beispiel einiger Arylsulfonsaeurederivate

In arylsulfonyl halides, the half-wave potentials of the corresponding chlorides and fluorides differ by more than 1000 mV, the fluoride being more negative; the influence of para-substituents is small for the chlorides, large for the fluorides.In agreement with the half-wave potentials, arylsulfonyl chlorides are considerably more reactive chemically than the corresponding fluorides.The O-selectivity found for P(O)F compounds is not observed in arylsulfonyl fluorides.Studies of competitive ester formation using primary and secondary alcohols and various arylsulfonyl chlorides yielded no clear analogy to the half-wave potentials.The primary alcohol is always sulfonated in preference to the secondary alcohol, whether the hydroxy functions are present in different molecules or the same molecule.In the latter case, the secondary hydroxyl function is then attacked in a further step by a second, different, arylsulfonyl chloride, giving the compounds 4-8.The further electroreduction of these diesters may be carried out in high yields, giving selective fission of one ester linkage only (that with the more positive potential) provided the difference in the half-wave potentials of the different ester linkages is sufficiently large.In the electroreductive fission the monosulfinic acid and the corresponding alcohol are liberated (see table II).In the competition reaction between phenol and 1:1 mixtures of tosyl chloride (A) and p-carboxyethyl-benzenesulfonyl chloride (B), the chloride with the more positive potential (B), E1/2=72 mV reacts quicker by a factor of 2.5.In competitive Finkelstein reactions, the selectivity was 1:11 at a difference in half-wave potentials of 760 mV (table IV).Arylsulfonates with free secondary alcohol functions may be oxidized smoothly and in high yield to the corresponding ketone using Na2Cr2O7 (3), without effecting the sulfonate linkage.The alkali hydrolysis of n-hexyl para-substituted arylsulfonates follows the Hammett relation but shows a lesser selectivity than was observed in the electroreductive fission of the same esters at the required potentials.Tables VI, VII and VIII concentrate on the preparative importance of the potential-controlled electroreductive fission of aliphatic and aromatic arylsulfonates.The corresponding hydroxy compounds are liberated in yields of up to over 90percent: N-alkyl- and N-aryl arylsulfonamides give analogous results. (table IX)