825-86-5

Basic information

• Product Name: 4-iodobenzenesulfonamide
• Synonyms: 4-iodobenzenesulfonamide
• CAS NO: 825-86-5
• Molecular Formula: C₆H₆INO₂S
• Molecular Weight: 283.09
• Mol File: 825-86-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 194 °C
• Boiling Point: 377.3°C at 760 mmHg
• Flash Point: 182°C
• Appearance: /
• Density: 2.015g/cm³
• Vapor Pressure: 6.82E-06mmHg at 25°C
• Refractive Index: 1.664
• PKA: 9.88±0.10(Predicted)
• CAS DataBase Reference: 4-iodobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-iodobenzenesulfonamide(825-86-5)
• EPA Substance Registry System: 4-iodobenzenesulfonamide(825-86-5)

Safety Data

• Hazardous Substances Data: 825-86-5(Hazardous Substances Data)

Usage

General Description

4-iodobenzenesulfonamide is a compound that belongs to the class of sulfonamides, which are organic compounds that contain a sulfonyl functional group attached to an amine group. It is a derivative of benzenesulfonamide, with an iodine atom substituted in the para position of the benzene ring. 4-iodobenzenesulfonamide has potential applications in medicinal chemistry, particularly as a building block for the synthesis of biologically active molecules. It can also be used in organic synthesis as a reagent for the introduction of the sulfonyl functional group into other molecules. Additionally, 4-iodobenzenesulfonamide has been studied for its antimicrobial and antifungal properties, making it a potential candidate for pharmaceutical development. Overall, this compound has diverse uses in the fields of medicinal chemistry and organic synthesis.

InChI:InChI=1/C6H6INO2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,(H2,8,9,10)

Upstream product

• 98-61-3 p-Iodobenzenesulfonyl chloride 
• 591-50-4 iodobenzene 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 

Downstream Products

• 99361-98-5 4-iodo-benzenesulfonic acid-(2,3-dihydroxy-propylamide) 
• 57598-18-2 1-<4-Jod-benzolsulfonyl>-3-butyl-harnstoff 
• 154377-75-0 N-(tert-butyloxycarbonyl)-4-iodobenzenesulfonamide 
• 918401-83-9 (E,E)-1,11-bis(tert-butoxycarbonyl)-1,11-bis[(2,4,6-triisopropylphenyl)sulfonyl]-6-[(4-iodophenyl)sulfonyl]-1,6,11-triazaundeca-3,8-diene 
• 939387-80-1 diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-sulfamoylphenyl)prop-1-enylphosphonate 
• 939387-82-3 diethyl 3-[N-acetyl-N-(hydroxy)amino]-1-(4-sulfamoylphenyl)propylphosphonate 
• 335004-32-5 (E)-N,N'-bis[(4-iodophenyl)sulfonyl]-2-butene-1,4-diamine 
• 335004-24-5 (E)-N,N'-bis(tert-butyloxycarbonyl)-N,N'-bis[(4-iodophenyl)sulfonyl]-2-butene-1,4-diamine 
• 335003-93-5 (E,E,E)-1,14-dibromo-N,N'-bis[(4-iodophenyl)sulfonyl]-5,10-diazatetradeca-2,7,12-triene 
• 153435-28-0 (4-Aminosulphonylphenyl)tributylstannane 
• 775331-26-5 4-((trimethylsilyl)ethynyl)benzenesulfonamide 
• 1061091-56-2 N-[(4-iodophenyl)sulfonyl]carbamic acid methyl ester 
• 1188541-86-7 4-{3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-pyrazol-1-yl]-prop-1-ynyl}-benzenesulfonamide 
• 1093252-17-5 4-iodo-N-[1-(4-methoxyphenyl)-ethylidene]-benzenesulfonamide 

Relevant articles and documents

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

New allyldithiocarbimate salts: Synthesis, structure and antifungal activity

Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.

Metal-free construction of primary sulfonamides through three diverse salts

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.