2266-41-3

Usage

Uses

Used in Organic Synthesis:
4-Fluorobenzenesulfonohydrazide is used as a reagent in organic synthesis for its ability to facilitate the formation of new chemical compounds. Its unique structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of pharmaceuticals and other organic molecules.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 4-Fluorobenzenesulfonohydrazide is utilized as a key intermediate in the production of certain drugs. Its presence in the manufacturing process is crucial for the synthesis of active pharmaceutical ingredients, contributing to the development of new medications.
Used in Agrochemical Production:
4-Fluorobenzenesulfonohydrazide is employed in the creation of agrochemicals, which are chemicals used in agricultural processes to enhance crop yield and protect plants from pests and diseases. Its role in this industry is vital for the development of effective and safe agrochemicals.
Used in Dye Production:
This chemical compound is also used in the production of dyes, where it contributes to the creation of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Safety Considerations:
Given its moderately hazardous nature, 4-Fluorobenzenesulfonohydrazide requires careful handling to prevent irritation to the skin, eyes, and respiratory system. It is essential to adhere to proper safety protocols when working with this chemical to mitigate any potential health risks.

Upstream product

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 16108-86-4 1-<4-Fluor-benzolsulfonylhydrazono>-1-<5-fluor-2-hydroxy-phenyl>-aethan 
• 132283-80-8 2,3a,4,5,6,7-Hexahydro-2-(4-fluorophenylsulphonyl)spiro<3H-indazole-3,3'(3H)-indole>-2'(1H)-one 
• 132283-83-1 4',5'-cyclopenta-2'-(4-fluorophenylsulphonyl)-4-trifluoromethylspiro-<3H-indole-3,3'-(3H)pyrazol>-2(1H)-one 
• 132283-82-0 C₂₁H₁₇F₄N₃O₃S 
• 2063-04-9 4-fluoro-N'-(4-hydroxy-3-methoxybenzylidene)benzenesulfonohydrazide 
• 2377-63-1 4-Dimethylamino-benzaldehyd-<4-fluor-benzol-sulfonyl-(1)-hydrazon> 
• 718-25-2 (E)-4-fluorostilbene 
• 397-54-6 2-(4-fluorophenyl)benzoxazole 
• 432-99-5 2-[(4-fluorophenyl)sulfonyl]-1-phenylethan-1-one 

Relevant academic research and scientific papers

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.

Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives

We report herein a direct method to synthesize 4-aryl-3-butenoic acid through a carboxylic-acid-directed oxidative Heck reaction. The various 4-aryl-3-butenoic acids are easily prepared in moderate to good yields. In view of the promising bioactivity of 4-phenyl-3-butenoic acid previously reported, its derivatives reported here may be bioactive.

Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.

Electrochemical fluorosulfonylation of styrenes

An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.

Iodine-Mediated Coupling of Cyclic Amines with Sulfonyl Hydrazides: an Efficient Synthesis of Vinyl Sulfone Derivatives

An efficient iodine-mediated coupling of cyclic amines with sulfonyl hydrazides is reported. This transformation opens a new route to the synthesis of vinyl sulfones derivatives, which is a common structural motif in natural products and pharmaceuticals. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.

NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.

Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones

Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.