2525-42-0

Basic information

• Product Name: (propadienylsulfonyl)benzene
• Synonyms: (1,2-Propadienylsulphonyl)benzene; (1,2-Propadienylsulphonyl)-benzene; (Propadienylsulfonyl)benzene; benzene, (1,2-propadienylsulfonyl)-; Phenyl propadienyl sulfone
• CAS NO: 2525-42-0
• Molecular Formula: C₉H₈O₂S
• Molecular Weight: 180.2236
• Mol File: 2525-42-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 349.2°C at 760 mmHg
• Flash Point: 210.1°C
• Density: 1.14g/cm³
• Vapor Pressure: 9.64E-05mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: (propadienylsulfonyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (propadienylsulfonyl)benzene(2525-42-0)
• EPA Substance Registry System: (propadienylsulfonyl)benzene(2525-42-0)

Safety Data

• Hazardous Substances Data: 2525-42-0(Hazardous Substances Data)

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 931-59-9 benzenesulfenyl chloride 
• 2525-40-8 prop-2-ynylsulfonylbenzene 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 4972-29-6 benzenesulphinyl chloride 
• 220961-10-4 ((2-bromo-2-propenyl)sulfonyl)benzene 
• 873-55-2 sodium benzenesulfonate 
• 108-98-5 thiophenol 
• 5651-88-7 phenyl propargyl sulfide 
• 37605-46-2 (propa-1,2-diene-1-sulfinyl)benzene 
• 4104-89-6 triphenylpropargyl stannane 
• 1595-38-6 phenylthioallene 
• 107-19-7 propargyl alcohol 

Downstream Products

• 107402-98-2 3-Benzenesulfonyl-2-methylene-hexahydro-isoxazolo[2,3-a]pyridine 
• 107403-02-1 2-methyl-3-(phenylsulfonyl)octahydropyridino<1,2-b>isoxazoline 
• 105064-92-4 2-(1-Benzenesulfonylmethyl-vinyl)-cyclopentanone 
• 105065-33-6 2-[2-Benzenesulfonyl-1-methyl-eth-(Z)-ylidene]-cyclopentanone 
• 105064-93-5 2-[2-Benzenesulfonyl-1-methyl-eth-(E)-ylidene]-cyclopentanone 
• 5000-44-2 1-phenylsulfonyl-2-propanone 
• 105064-99-1 2-[2-Benzenesulfonyl-1-methyl-eth-(E)-ylidene]-cyclohexanone 
• 105064-94-6 2-(1-Benzenesulfonylmethyl-vinyl)-cyclohexanone 
• 94371-35-4 (1S,4R,5S)-5-Benzenesulfonyl-7-isopropylidene-6-methylene-bicyclo[2.2.1]hept-2-ene 
• 94371-35-4 (1R,4S,5S)-5-Benzenesulfonyl-7-isopropylidene-6-methylene-bicyclo[2.2.1]hept-2-ene 
• 94371-63-8 3-Benzenesulfonyl-2-methyl-6H-cyclohepta[b]furan 
• 94371-62-7 (3S,3aR)-3-Benzenesulfonyl-2-methylene-3,3a-dihydro-2H-cyclohepta[b]furan 
• 94371-67-2 3-Benzenesulfonyl-2-methyl-1-p-tolyl-1,6-dihydro-cyclohepta[b]pyrrole 
• 75233-09-9 (2-Cyclohex-1-enylmethyl-prop-2-ene-1-sulfonyl)-benzene 

Relevant articles and documents

The Diels-Alder Reaction of Furan and Phenylsulphonylpropadiene. The Simple Base Induced Rearrangement of 3-Methylene-2-endo-phenylsulphonyl-7-oxabicyclohept-5-ene

The Diels-Alder reaction of furan and phenylsulphonylpropadiene gives predominantly the 7-oxabicycloheptene (1), whose hydrogenation products (3) and (4) provide a simple entry to the synthesis of substituted cyclohexenols.

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions

In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.

Sulfinate-Organocatalyzed (3+2) Annulation of Allenyl Sulfones with 1,1-Dicyano Olefins in the Presence of a Quaternary Ammonium Phase Transfer Agent

The benzenesulfinate-catalyzed (3+2) annulation between allenyl sulfones and aryl(alkyl)idenemalononitriles has been developed under mild phase transfer conditions, affording a breadth of functionalized sulfonyl cyclopentenes in good to excellent yields (