29959-86-2

Basic information

• Product Name: Piperidine, 1-(phenylthio)-
• CAS NO: 29959-86-2
• Molecular Formula: C11H15NS
• Molecular Weight: 193.313
• Mol File: 29959-86-2.mol

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-(phenylthio)-(29959-86-2)
• EPA Substance Registry System: Piperidine, 1-(phenylthio)-(29959-86-2)

Safety Data

• Hazardous Substances Data: 29959-86-2(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 123-91-1 1,4-dioxane 
• 741252-70-0 tris-methanesulfonyl-phenylsulfanyl-methane 
• 14204-35-4 5,5-Dimethyl-3-phenylthiohydantoin 
• 258822-89-8 3-Phenylsulfenyl-2-(N-cyanoimino)thiazolidine 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 3541-14-8 phenyl toluene-4-thiosulfonate 
• 139-66-2 diphenyl sulfide 

Downstream Products

• 1523523-71-8 1-(S-phenylsulfonimidoyl)piperidine 
• 98-10-2 benzenesulfonamide 
• 939-48-0 isopropyl benzoate 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 82946-84-7 1-methyl-2-phenyl-3-(phenylthio)-1H-indole 

Relevant articles and documents

Sulfinimidate Esters as an Electrophilic Sulfinimidoyl Motif Source: Synthesis of N-Protected Sulfilimines from Grignard Reagents

In this work we investigated, for the first time, the reactivity of sulfinimidate esters as an electrophilic sulfinimidoyl motif source. The reaction of such sulfinimidate esters with Grignard reagents enables the preparation of protected sulfilimines in

Synthesis of Sulfinamidines and Sulfinimidate Esters by Transfer of Nitrogen to Sulfenamides

In this work we report a new synthetic tactic for the straightforward preparation of hardly accessible sulfinamidines and sulfinamide esters, by using a simple metal-free protocol. The process is robust and uses readily available sulfenamides as the S-don

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate

Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6-sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles.

Transition-Metal-Free Thioamination of Arynes Using Sulfenamides

The insertion of arynes into the S-N σ-bond of sulfenamides allowing the synthesis of o-sulfanylaniline derivatives with reasonable functional group compatibility is presented. The aryne generated from 2-(trimethylsilyl)aryl triflates using CsF in DME was the key for the success of this transition-metal-free thioamination reaction, which involves new C-N and C-S bond formations in a single step under mild conditions. Moreover, the synthetic potential of this method was demonstrated by the synthesis of the antidepressant drug vortioxetine.

Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines

The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides.

AlCl3-catalyzed insertion of isocyanides into nitrogen-sulfur bonds of sulfenamides

Lewis acid-catalyzed insertion of isocyanides 2 into nitrogen-sulfur bonds of sulfenamides 1 was developed. This method provided a convenient method for the synthesis of isothioureas 3. Among Lewis acids examined, AlCl3 brought about the best result. Acetic acid assisted one-pot preparation of unsymmetrical ureas was also described.

Copper-catalyzed formation of sulfur-nitrogen bonds by dehydrocoupling of thiols with amines

Copper-catalyzed formation of sulfur-nitrogen bonds can be performed by a dehydrocoupling of aryl thiols with amines. Sulfenamides or sulfonamides can be produced by the use of a copper catalyst in air or under oxygen atmosphere. Furthermore, a reaction involving the combination of a palladium catalyst and a copper catalyst selectively afforded sulfinamides.

Copper-catalyzed synthesis of sulfenamides utilizing diaryl disulfides with alkyl amines

The copper-catalyzed coupling of diaryl disulfides with alkyl amines can afford various sulfenamides in good yields. Furthermore, the present reaction is efficient and can be used for both of the aryl sulfide groups on disulfide. Georg Thieme Verlag Stutt

A new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine, and its optically active version

We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the α-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon α-sulfenylation of a cyclic β-keto ester.

In Search of New Sulfur Transfer Agents

The chemistry of various sulfur-transfer agents is studied.The reaction of aromatic sulfenyl chloride 5 in the presence of imidazole and/or triethylamine gives the aryl disulfides 7 in 14-85 percent yield, whereas in the case of the corresponding benzylsulfenyl chlorides 9 in the presence of triethylamine and/or caprolactam, both disulfide 10 and benzyl chlorides 11 are formed in 0-81 precent and 10-72 precent yield, respectively. - The transfer reactions of 3-sulfenylated hydantoins 18 with amines are useful for the preparation of the unsymmetric sulfenamides 20 in 31 -61 percent yield.Analogous transfer reactions of compounds 23 and 24 with piperidine give N,N'-thiodipiperidine (3, X = CH2) in 71-80 percent.