16192-04-4

Usage

Sulfone derivative

benzene
1-methyl-4-[(2-methylprop-2-en-1-yl)sulfonyl]benzene is derived from benzene by attaching a sulfonyl group to the benzene ring.

Methyl group

present
The compound contains a methyl group (CH3) as part of its structure.

Sulfonyl group

present
A sulfonyl group (SO2) is attached to the benzene ring in the compound.

Alkyne group

2-methylprop-2-en-1-yl
The compound contains a 2-methylprop-2-en-1-yl group, which is an alkyne group with a double bond between the first and second carbon atoms, and a methyl group attached to the second carbon.

Physical state

colorless liquid at room temperature
1-methyl-4-[(2-methylprop-2-en-1-yl)sulfonyl]benzene is a colorless liquid when it is at room temperature.

Stability

stable under normal conditions
The compound is considered to be stable and does not readily undergo chemical reactions under standard conditions.

Industrial applications

pharmaceutical and chemical industries
1-methyl-4-[(2-methylprop-2-en-1-yl)sulfonyl]benzene is commonly used as a building block for the synthesis of various organic compounds in the pharmaceutical and chemical industries.

Health and environmental hazards

handle with caution
It is important to handle 1-methyl-4-[(2-methylprop-2-en-1-yl)sulfonyl]benzene carefully, as it may pose health and environmental risks if not properly managed.

Upstream product

• 3536-96-7 vinylmagnesium chloride 
• 143100-97-4 1-((2-(chloromethyl)allyl)sulfonyl)-4-methylbenzene 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 563-47-3 3-Chloro-2-methylpropene 
• 16192-08-8 p-tolylsulfonylallene 
• 917-54-4 methyllithium 
• 16192-03-3 1-methyl-4-[(2-methylprop-1-en-1-yl)sulfonyl]benzene 
• 941-55-9 4-toluenesulfonyl azide 
• 2591-44-8 β-methallyltriphenylstannane 
• 90395-99-6 1-(2-Chloro-2-methyl-propane-1-sulfonyl)-4-methyl-benzene 
• 54844-24-5 2-Methyl-2-propenyl 4-methylphenyl sulfide 
• 103-19-5 di(p-tolyl) disulfide 
• 513-42-8 3-hydroxy-2-methyl-1-propene 

Downstream Products

• 70918-76-2 4-<(1-hexyl-2-methylprop-2-enyl)sulphonyl>toluene 
• 54857-15-7 5-Methyl-1,3-diphenyl-4-(toluene-4-sulfonyl)-hex-5-en-1-one 
• 105465-41-6 1-[2-Methyl-3-(toluene-4-sulfonyl)-propyl]-pyrrolidine 
• 75950-55-9 1-(2,6-Dimethyl-hepta-1,5-diene-3-sulfonyl)-4-methyl-benzene 
• 146904-20-3 2,7-dimethyl-3-(p-tolylsulfonyl)octa-1,6-diene 
• 120780-86-1 2-methyl-3-p-tolylsulphonyloct-1-en-7-yne 
• 139591-74-5 1-[1-Acetyl-3-bromomethyl-4-(toluene-4-sulfonylmethyl)-cyclopentyl]-ethanone 
• 131035-87-5 Dimethyl trans-4-bromomethyl-3-tosylmethylcyclopentane-1,1-dicarboxylate 
• 131035-87-5 Dimethyl cis-4-bromomethyl-3-tosylmethylcyclopentane-1,1-dicarboxylate 
• 135979-20-3 methyl 3-(3-methyl-3-buten-1-yl)-4-p-toluenesulfonylmethyl-cyclopentane-1,1-dicarboxylate 
• 127368-22-3 3-Chloromethyl-4-(toluene-4-sulfonylmethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester 
• 120780-81-6 2,7-dimethyl-3-p-tolylsulphonylocta-1,7-diene 
• 121824-99-5 chloromethyl-3 tosylmethyl-4 N-tosyl pyrrolidine 
• 121824-99-5 chloromethyl-3 tosylmethyl-4 N-tosyl pyrrolidine 

Relevant academic research and scientific papers

SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.

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.

Coupling reaction of magnesium alkylidene carbenoids with α-sulfonylallyllithiums: An efficient route to multi-substituted vinylallenes

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as α-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of α-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield. Georg Thieme Verlag KG Stuttgart · New York.

Visible-light-induced photoreductive generation of radicals from epoxides and aziridines

It's a trap! Both epoxides and aziridines substituted by an aryl ketone can be reduced efficiently using visible-light photoredox catalysts. The radicals generated were trapped by allyl sulfones, and formed α-branched β-hydroxy or amino derivatives with high diastereocontrol (see scheme; dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine, ppy=2-phenylpyridine). Copyright

Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: Homolytic allylation at nitrogen

4-Methylbenzenesulfonyl azide reacts with allyltriphenylstannane (ATPS) in refluxing benzene, in the presence of 2,2′-azobis(2-methylpropionitrile) as initiator, to give N-allyl-4-methylbenzenesulfonamide in good yield after hydrolytic work-up. Small amounts of allyl 4-methylphenyl sulfone were also formed. The reaction follows a free-radical chain mechanism which involves competitive addition of Ph5Sn? to Na and to Nc of the azido group in ArSO2NaNbNc. Addition to Na followed by loss of nitrogen gives ArSO2NSnPh3, the precursor of the N-allylarenesulfonamide, while addition to Nc leads to the formation of ArSO2 and thence to the allyl aryl sulfone. Allyltrimethylstannane behaves in a similar way to ATPS, but allyltributylstannane gives only a low yield of N-allylarenesulfonamide and the major product is the unsubstituted sulfonamide MeC6H4SO2NH2, which results because the radical ArSO2NSnBu3 undergoes intramolecular 1,5-hydrogen-atom transfer in preference to adding to the allylstannane. 2-Methylallyltriphenylstannane reacts in an analogous way to ATPS, but allylstannanes containing non-terminal double bonds do not react successfully. The arenesulfonyl azides 4-XC6H4SO2N3 (X = H, MeO, F) react in a similar way to tosyl azide, but the reaction is very sluggish when X = NO2? With 1-octanesulfonyl azide, reaction with Ph3Sn? is much less selective and products arising from attack at Na and Nc are formed in comparable yields. Ethyl azidoformate reacts with allylstannanes in a similar manner to, although more slowly than, tosyl azide and gives good yields of the corresponding allylic carbamates.

2-(Chloromethyl)-3-tosylpropene: An useful reagent for the synthesis of allyl sulfones

2-(Chloromethyl)-3-tosylpropene (5) prepared directly from commercially available 3-chloro-2-(chloromethyl)propene reacts with a variety of heteronucleophiles and Grignard derivatives to afford allyl sulfones 7 and 8 respectively. It reacts also with elec

Efficient synthesis of sulphones using polysorbate-80 as phase transfer catalyst

A very easy and practical method of preparing sulphones from alkyl halides has been developed using Polysorbate-80 as phase transfer catalyst.

A simple and rapid preparation of sulfones from alkyl halides using ultrasound

Appropriate alkyl halides and sodium p-toluenesulfinates react rapidly in DMF-water at room temperature under the influence of ultrasound to afford sulfones. Using this procedure a wide variety of sulfones have been prepared.

Substituted Lithium (E)-3-Lithio-3-tosyl-2-propenolates: Useful Intermediates in Organic Synthesis

The lithiation of substituted tosylated epoxides 7 derived from allylic sulfones with methyllithium leads to lithium (E)-3-lithio-3-tosyl-2-propenolates 5 in a stereoselective manner.The further reaction of these intermediates with different electrophilic

A NEW GENERAL SYNTHESIS OF SULFONES FROM ALKYL OR ARYL HALIDES AND p-TOLUENESULFONHYDRAZIDE

Here we report the utilization of commercially available p-toluenesulfonhydrazide as a new nucleophilic reagent in displacement reactions with suitable halides for an improved, general synthesis of sulfones.Good results are obtained with primary, secondary, allylic, benzylic, and aromatic halides activated by withdrawing groups.