2588-51-4

Usage

Chemical structure

1-(butylsulfonyl)piperidine consists of a piperidine ring with a butylsulfonyl group attached to it.

Functional groups

The compound contains a piperidine ring (a six-membered nitrogen-containing ring) and a butylsulfonyl group (a butyl group connected to a sulfonyl group).

Molecular weight

Approximately 203.32 g/mol

Appearance

It is typically a colorless to pale yellow liquid or solid, depending on the temperature and concentration.

Solubility

1-(butylsulfonyl)piperidine is soluble in organic solvents such as ethanol, methanol, and dichloromethane.

Reactivity

The compound is known for its ability to react with a variety of other compounds, making it useful in a wide range of chemical reactions and processes.

Applications

It is commonly used as an intermediate or reagent in organic synthesis, particularly in pharmaceutical and industrial applications.

Building block

Its structure and reactivity make it a valuable building block for the synthesis of more complex organic molecules.

Versatility

1-(butylsulfonyl)piperidine is a versatile and important chemical compound with a wide range of potential applications.

Upstream product

• 110-89-4 piperidine 
• 7559-57-1 n-butyl α-disulfone 
• 78186-30-8 1-(Butylsulfinyl)piperidine 
• 109-72-8 n-butyllithium 
• 51029-15-3 1-(trifluoromethanesulfonyl)piperidine 

Relevant academic research and scientific papers

Triflamides: Elimination of the triflyl anion versus substitution of the trifluoromethide group

Base-induced elimination of CF3SO2- and nucleophilic substitution of CF3- were observed in the reaction of secondary triflamides with alkyllithium reagents.

Substitution Reactions of Alkanesulfonyl Derivatives: Direct Substitution vs. Elimination-Addition Mechanisms in Substitution Reactions of Alkyl α-Disulfones

The reactions of a series of alkyl and aralkyl α-sulfones, RSO2SO2R ( R = Me, n-Bu, i-Pr, ArCH2) with a variety of nucleophiles in aqueous dioxane have been examined.Both rates of reaction and whether a given reaction takes place by an elimination-addition (sulfene intermediate) or a direct substitution (attack of nucleophile on SO2 group of α-sulphone) mechanism have been determined.The great majority of substitution reactions of alkyl α-disulfones take place via an elimination-addition mechanism (eq 3a), with formation of a sulphene from the α-disulphone being rate determining.Only when nucleophile is one, like azide ion, that is weakly basic while still being a good nucleophile is a direct substitution the preferred pathway.Even with azide the reaction pathway changes to elimination-addition when the acidity of the hydrogens on the carbon adjacent to the sulfonyl group is increased sufficiently, as in (PhCH2SO2)2.Comparison of rates of elimination of α-disulphones (R'CH2SO2)2 with rates of base-catalyzed hydrogen exchange of the corresponding trifluoromethyl sulfones R'CH2SO2CF3 indicates that formation of sulfenes from α-disulfones involves either an irreversible E1cB or a very E1cB-like E2 mechanism, a conclusion that is also supported by the observed variation of the rate of elimination of RR'CHSO2SO2R'' with changes in R and R'.Comparison of the behavior of an alkyl α-disulfone with that of the corresponding alkanesulfonyl chloride reveals that changing Y in RCH2SO2Y from RSO2 to Cl causes direct substitution to be able to compete much more effectively with elimination-addition.Kinetic studies show that this arises because, for a given nucleophile, (a) elimination-addition is 5-10 times slower for the alkanesulfonyl chloride than for the α-disulfone while (b) the rate of direct substitution is 5-10 times faster for the sulfonyl chloride.The origin of these rate differences is discussed and explained.