2751-27-1

Basic information

• Product Name: 4-Iodobenzenesulfonohydrazide
• Synonyms: 4-Iodobenzenesulfonohydrazide
• CAS NO: 2751-27-1
• Molecular Formula: C₆H₇IN₂O₂S
• Molecular Weight: 298.10145
• Mol File: 2751-27-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-Iodobenzenesulfonohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodobenzenesulfonohydrazide(2751-27-1)
• EPA Substance Registry System: 4-Iodobenzenesulfonohydrazide(2751-27-1)

Safety Data

• Hazardous Substances Data: 2751-27-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Iodobenzenesulfonohydrazide is used as a reagent in organic synthesis for its ability to facilitate the preparation of various pharmaceuticals, agrochemicals, and other organic compounds. Its role in the synthesis of heterocycles, especially sulfonamide and sulfonyl hydrazones, makes it a valuable component in the development of new chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodobenzenesulfonohydrazide is used as a key intermediate in the synthesis of drugs, contributing to the development of new therapeutic agents. Its antimicrobial and antifungal properties also make it a potential candidate for the treatment of infections.
Used in Agrochemical Industry:
4-Iodobenzenesulfonohydrazide is utilized in the agrochemical industry for the preparation of various agrochemicals, including pesticides and herbicides, due to its reactivity and potential to form active ingredients.
Used in Corrosion Inhibition:
4-Iodobenzenesulfonohydrazide has been investigated for its potential use as a corrosion inhibitor, which could be applied in various industries to protect materials from degradation and extend their service life.
Used in Analytical Chemistry:
In analytical chemistry, 4-Iodobenzenesulfonohydrazide is used as a reagent for the determination of various metals, providing a method for accurate metal analysis in different samples.

Upstream product

• 98-61-3 p-Iodobenzenesulfonyl chloride 

Downstream Products

• 108844-90-2 4-iodo-benzenesulfonic acid-(N'-ξ-D-glucopyranosyl-hydrazide) 
• 18559-20-1 D-erythro-Pentulose-<4-jod-benzolsulfonylhydrazon> 
• 1448709-49-6 3-((4-iodophenyl)thio)-1H-indole 
• 1554261-69-6 C₁₆H₁₇IOS 
• 3001-15-8 4,4'-diiodobiphenyl 
• 861083-81-0 (4-iodophenyl)(4-methoxyphenyl)thioether 
• 4241-66-1 4-Iodobenzenesulphonyl Fluoride 

Relevant articles and documents

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.

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

The synthesis of sulfonated 4: H -3,1-benzoxazines via an electro-chemical radical cascade cyclization

A new route for the synthesis of sulfonated 4H-3,1-benzoxazines has been accomplished by electrochemical radical cascade cyclizations of styrenyl amides with sulfonylhydrazines. This process demonstrates a wide substrate scope with diverse functional group compatibility under metal- and external oxidant-free conditions at ambient temperature.

Palladium-Catalyzed Regio- and Stereoselective Coupling-Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling-addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar(C)-S and S-N bonds, which are simultaneously incorporated onto the terminal carbon atom of an alkyne molecule.

Copper-Catalyzed Radical Cascade Cyclization to Access 3-Sulfonated Indenones with the AIE Phenomenon

An efficient copper-catalyzed radical cascade cyclization strategy was developed, by which a wide variety of 3-sulfonyl substituted indenones were prepared in one pot via reaction of 2-alkynylbenzonitriles with sulfonyl hydrazides in the presence of TBHP and CuI under mild reaction conditions. Much more importantly, the 3-sulfonyl indenones, synthesized through our newly developed copper-catalyzed radical cascade cyclization strategy, were found to own typical aggregation-induced emission (AIE) properties, showing orange to red emission with large Stokes shift (more than 135 nm). In addition, such newly found AIEgens could be successfully used in live cell imaging, exhibiting excellent biocompatibility and application potential.

Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study

A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.

Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes

A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.

Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water

A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.

Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: An electrochemical mechanistic study

Copper(i) halides were used as mediators in the synthesis of β-hydroxysulfones via the oxysulfonylation of styrenes using sulfonylhydrazides. The feature of the developed process lies in the combination of a copper(i) salt with oxygen - the stoichiometric oxidant. Copper(ii) species are responsible for the oxidation of sulfonylhydrazides, they are generated in small amounts in the O2/Cu(i)/Cu(ii) redox system, which is formed during the reaction. The combination of these three components enables one to obtain in the case of α-methylstyrenes only β-hydroxysulfones and in the case of α-unsubstituted styrenes, β-hydroxysulfones as the main products and β-ketosulfones as the by-products. With good yields β-hydroxysulfones were prepared by reduction of the reaction mixture containing both products β-hydroxysulfones and β-ketosulfones with NaBH4. An electrochemical study revealed that the Cu(i)/Cu(II) pair can serve as an effective mediator of β-hydroxysulfones formation via redox processes.

Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides

A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.