20605-46-3

Basic information

• Product Name: Benzene, [(3-phenyl-2-propenyl)sulfonyl]-
• Synonyms: cinnamylsulfonylbenzene;(cinnamylsulfonyl)benzene;(3-phenylsulfonylpropenyl)benzene;Phenylcinnamylsulfon
• CAS NO: 20605-46-3
• Molecular Formula: C15H14O2S
• Molecular Weight: 258.341
• Mol File: 20605-46-3.mol

Chemical Properties

• CAS DataBase Reference: Benzene, [(3-phenyl-2-propenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(3-phenyl-2-propenyl)sulfonyl]-(20605-46-3)
• EPA Substance Registry System: Benzene, [(3-phenyl-2-propenyl)sulfonyl]-(20605-46-3)

Safety Data

• Hazardous Substances Data: 20605-46-3(Hazardous Substances Data)

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 98-09-9 benzenesulfonyl chloride 
• 16212-05-8 (allylsulfonyl)benzene 
• 960-16-7 tributylphenylstannane 
• 3112-85-4 methylphenylsulfonate 
• 103-64-0 bromostyrene 
• 98-80-6 phenylboronic acid 
• 104-54-1 3-Phenylpropenol 
• 873-55-2 sodium benzenesulfonate 
• 145490-75-1 N-fluorobenzene sulfonamide 
• 300-57-2 allylbenzene 
• 29690-28-6 N,N-difluorobenzenesulfonamide 
• 618-41-7 Benzenesulfinic acid 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 19752-23-9 cinnamyltrimethylsilane 
• 1449482-35-2 2'-benzenesulfonyl-4-dimethylamino[1,1';4',1]terphenyl 
• 1449482-34-1 2'-benzenesulfonyl-3,4-methylenedioxy[1,1';4',1]terphenyl 
• 1449482-33-0 2'-benzenesulfonyl-4-fluoro[1,1';4',1'']terphenyl 
• 1449482-32-9 2'-benzenesulfonyl-4-methoxy[1,1';4',1]terphenyl 
• 1449482-31-8 2'-benzenesulfonyl[1,1';4',1]terphenyl 

Relevant articles and documents

Difluoroaminosulfonylation of Styrenes with N,N-Difluorobenzenesulfonamide

A new type of difluoroaminosulfonylation of styrenes with N,N-difluorobenzenesulfonamide (DFBSA) was developed, using NiCl2/Mn as catalysts and bipyridine as the ligand, to afford a series of 1-difluoroamino-2-phenylsulfonyl products. Preliminary mechanistic studies proved a free radical process for the reaction.

Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide

A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.

Water-Promoted Dehydrative Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols with Sulfinic Acids

A mild, green and extra activator-free synthesis of allylic sulfones from non-derivatized allylic alcohols and sulfinic acids was developed and only the easily-available Pd(PPh3)4 was used as the catalyst. This new method could be easily scaled up to gram scale, affording the target allylic sulfones in a nearly quantitative yield with water as the sole by-product. Mechanism studies both by various NMR techniques and by theoretical calculations suggested two reaction pathways may be involved in the reaction, which are dependent on the reaction media, that is, an eight-membered ring binding species may be formed in aqueous media between allylic alcohol, sulfinic acid and water, while a six-membered ring binding species may be formed in common aprotic organic solvent between allylic alcohol and sulfinic acid. Both binding species may be accounted for the efficient activation of allylic alcohols via hydrogen bonding.

Synthetic method for allyl sulfone

The invention belongs to the field of organic synthesis, and especially relates to a synthetic method for allyl sulfone. The synthetic method for allyl sulfone is provided. Protonic acid can be simultaneously added as an additive under the catalysis of a

Visible-Light-Mediated Reactions of Electrophilic Radicals with Vinyl and Allyl Trifluoroborates

Visible-light photoredox catalysis enables the vinylation and allylation of electrophilic radicals with readily available potassium trifluoroborate reagents. The processes show good functional group compatibility, and mechanistic and computational studies

Palladium-catalyzed allylation of sulfonyl hydrazides with alkynes to synthesize allylic arylsulfones

A novel method for the construction of allyl arylsulfone derivatives was developed by palladium catalyzed allylation of sulfonyl hydrazides with alkynes. A series of structurally diverse allyl arylsulfones can be regioselectively synthesized in high yields under mild conditions.

Ring Expansion of Epoxides under Br?nsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines

A novel ring-expansion reaction of epoxides under Br?nsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Br?nsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Br?nsted base catalyst to generate α,β-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.

One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions

A metal-free tandem procedure by using a sulfonylation reaction of aryl allylic alcohols followed by an iodobenzenediacetate (PIDA)-promoted oxidative functionalization has been established. Allylic sulfones, γ-ketosulfones, and triflyl allylic alcohols have been constructed in a single operation. The methodology incorporates the sulfonyl (both aryl and triflyl) functionality with a simple work-up procedure.

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers

A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).

One-pot synthesis of substituted tetrahydrocyclobuta[a]naphthalenes by domino aldol condensation/olefin migration/electrocyclization

A facile one-pot synthetic route for preparing the novel benzofused tricyclic skeleton of 1,2,2a,8b-tetrahydrocyclobuta[a]naphthalenes 5 is developed. The route was realized by a NaH-mediated tandem aldol condensation/olefin migration/electrocyclization of o-allylbenzaldehydes 1 with cinnamyl sulfones 3 in good yields.