3729-44-0

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

Downstream Products

• 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 
• 32353-97-2 (E)-4,4'-(prop-1-ene-1,3-diyldisulfonyl)bis(chlorobenzene) 
• 1445598-33-3 diethyl 1-(4-chlorophenylsulfonyl)-3-nitropentan-3-ylphosphonate 
• 1260118-86-2 1-(4-(3-((4-chlorophenyl)sulfonyl)propyl)phenyl)ethanone 
• 16733-61-2 4-[2-(4-chloro-benzenesulfonyl)-1-methyl-ethyl]-morpholine 

Relevant academic research and scientific papers

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.

Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO

We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.

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.

Facile synthesis of substituted diaryl sulfones: Via a [3 + 3] benzannulation strategy

A base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane intermediate.

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.

Vanadium-catalyzed enantioselective oxidation of allyl sulfides

The enantioselective oxidation of allyl sulfides with a vanadyl complex of 3,5-diiodosalicylidene tert-leucinol as a catalyst and aqueous hydrogen peroxide as an oxidant afforded chiral allyl sulfoxides with high enantioselectivities of up to 97.3% ee and moderate yields.

Hydride affinities of cumulated, isolated, and conjugated dienes in acetonitrile

(Chemical Equation Presented) The hydride affinities (defined as the enthalpy changes in this work) of 15 polarized dienes [five phenyl sulfone substituted allenes (1a), the corresponding five isolated dienes (1b), and the corresponding five conjugated dienes (1c)] in acetonitrile solution were determined by titration calorimetry for the first time. The results display that the hydride affinity scales of the 15 dienes in acetonitrile range from -71.6 to -73.9 kcal/mol for 1a, from -46.2 to -49.7 kcal/mol for 1b, and from -45.0 to -46.5 kcal/mol for 1c, which indicates that the hydride-obtaining abilities of the cumulated dienes (1a) are not only much larger than those of the corresponding conjugated dienes (1c) but also much larger than those of the corresponding isolated dienes (1b). The hydrogen affinities of the 15 dienes as well as the hydrogen affinities and the proton affinities of the radical anions of the dienes (1-.) in acetonitrile were also evaluated by using relative thermodynamic cycles according to Hess's law. The results show that (i) the hydrogen affinities of the neutral dienes 1 cover a range from -44.5 to -45.6 kcal/mol for 1a, from -20.4 to -21.4 kcal/ mol for 1b, and from -17.3 to -18.5 kcal/mol for 1c; (ii) the hydrogen affinities of the radical anions of the dienes (1-.) in acetonitrile cover a range from -40.6 to -47.2 kcal/mol for 1a-., from -21.6 to -29.6 kcal/mol for 1b-., and from -10.0 to -15.4 kcal/mol for 1c-.; (iii) the proton affinities of the 15 1a-. in acetonitrile cover a range from -97.0 to -100.6 kcal/mol for 1a-., from -77.8 to -83.4 kcal/ mol for 1b -., and from -66.2 to -68.9 kcal/mol for 1c-.. The main reasons for the great difference between the cumulated dienes and the corresponding isolated and conjugated dienes in the hydride affinity, hydrogen affinity, and proton affinity have been examined. It is evident that these experimental results should be quite valuable to facilitate the elucidation of the origins of the especially high chemical potencies of the allenes, the choice of suitable hydride reducing agents to reduce the dienes, and the analyses on the reduction mechanisms.

Ether aryl sulfonic acid esters with improved antimalarial/anticancer activities

Our previous report showed that our current benchmark agent, 4-methoxyphenyl p-toluenesulibnate, is a selective antimalarial/anticancer agent. A series of related sulfones and sulfonic acid esters is now examined. 4-Allyloxyphenyl p-toluenesulfonate is a superior antimalarial/anticancer agent. 4-Methoxyphenyl 4-nitrobenzenesulfonate is a superior antimalarial agent, but shows poorer inhibition of human skin cancer cells. CSIRO 2006.

Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media

A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.

Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones

The bismuth or cadmium-catalyzed coupling reaction between aryl and alkyl sulfonyl chlorides and allylic halides proceeds smoothly to provide excellent yields of allylic sulfones at ambient temperature.