3729-44-0

Basic information

• Product Name: 1-chloro-4-(prop-2-en-1-ylsulfonyl)benzene
• Synonyms: 1-(Allylsulfonyl)-4-chlorobenzene; 4-chlorophenyl prop-2-en-1-yl sulfone; Allyl 4-chlorophenyl sulfone; benzene, 1-chloro-4-(2-propen-1-ylsulfonyl)-
• CAS NO: 3729-44-0
• Molecular Formula: C₉H₉ClO₂S
• Molecular Weight: 216.6846
• Mol File: 3729-44-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 351.3°C at 760 mmHg
• Flash Point: 166.2°C
• Density: 1.265g/cm³
• Vapor Pressure: 8.41E-05mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: 1-chloro-4-(prop-2-en-1-ylsulfonyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-4-(prop-2-en-1-ylsulfonyl)benzene(3729-44-0)
• EPA Substance Registry System: 1-chloro-4-(prop-2-en-1-ylsulfonyl)benzene(3729-44-0)

Safety Data

• Hazardous Substances Data: 3729-44-0(Hazardous Substances Data)

Usage

Category

Organochlorine compound

Physical state

White crystalline solid

Solubility

Soluble in non-polar solvents

Uses

Building block in organic synthesis, reagent in the preparation of sulfone compounds

Physical properties

Strong irritant to eyes and skin

Environmental impact

Potential environmental hazard, toxicity to aquatic organisms

Applications

Versatile chemical reagent in organic chemistry

Upstream product

• 5296-64-0 allyl phenyl thioether 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 14370-82-2 allyl phenyl selenide 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 106-95-6 allyl bromide 
• 15446-14-7 1-allylsulfanyl-4-chloro-benzene 
• 930-69-8 sodium thiophenolate 
• 106-54-7 p-Chlorothiophenol 
• 1679-18-1 4-Chlorophenylboronic acid 

Downstream Products

• 16733-61-2 4-[2-(4-chloro-benzenesulfonyl)-1-methyl-ethyl]-morpholine 
• 1745-18-2 1-allyl-4-chlorobenzene 
• 150666-85-6 3-(4-Chloro-benzenesulfonyl)-propan-1-ol 
• 91483-45-3 (R)-3-(4-Chloro-benzenesulfonyl)-2-methyl-pent-4-en-2-ol 
• 91483-45-3 (S)-3-(4-Chloro-benzenesulfonyl)-2-methyl-pent-4-en-2-ol 
• 20058-13-3 p-Chlor-phenyl-(2,3-dibrom-propyl)-sulfon 
• 1260118-86-2 1-(4-(3-((4-chlorophenyl)sulfonyl)propyl)phenyl)ethanone 
• 1445598-33-3 diethyl 1-(4-chlorophenylsulfonyl)-3-nitropentan-3-ylphosphonate 
• 32353-97-2 (E)-4,4'-(prop-1-ene-1,3-diyldisulfonyl)bis(chlorobenzene) 

Relevant articles and documents

Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution

Despite their unique potential as rare 1,1-dipole synthons, allyl sulfones are rarely used in target-oriented syntheses, likely due to the lack of a general catalytic method for their branch-selective allylic substitution. Herein, we identified allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated α-derivatization and subsequent cobalt-catalyzed allylic substitution. The sequential transformations allow for highly regioselective access to branched allylic substitution products with a variety of aliphatic side chains. The photoredox-enabled cobalt catalysis is indispensable for achieving high yields and regioselectivity for the desulfonylative substitution in contrast to traditional metal-catalyzed protocols, which lead to inferior outcomes in the corresponding transformations.

A practical synthesis of functionalized isoindolinones via [3?+?3] benzannulation of 1,3-bissulfonylpropenes and 4-arylmethylene-2,3-dioxopyrrolidines

A straightforward synthesis of isoindolinones has been developed via a [3 + 3] benzannulation of 4-arylmethylene-2,3-dioxopyrrolidines and 1,3-bissulfonylpropenes (or 4-sulfonylcrotonates). A series of functionalized isoindolinones were obtained in excellent yields. The reaction could be carried out under mild conditions without transition metal catalyst. The finding provides a practical approach for the preparation of isoindolinone derivatives with potential biological activities.

Direct N-H/α,α,β,β-C(sp3)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles

A protocol for the direct functionalization of N-H/α,α,β,β-C(sp3)-H of piperidine without any metal or external oxidants is reported. This reaction is promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This is a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties.