1126-80-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 2146, 1959 DOI: 10.1021/ja01518a032

InChI:InChI=1/C10H14S/c1-2-3-9-11-10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3

Upstream product

• 109-65-9 1-bromo-butane 
• 3111-52-2 potassium thiophenolate 
• 542-69-8 1-iodo-butane 
• 930-69-8 sodium thiophenolate 
• 106-98-9 1-butylene 
• 108-98-5 thiophenol 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 882-33-7 diphenyldisulfane 
• 13133-62-5 thiophenolate 
• 693-03-8 n-butyl magnesium bromide 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 

Downstream Products

• 17839-61-1 (S-butyl)-2-thiosalicylic acid 
• 65-85-0 benzoic acid 
• 121392-35-6 1-Bromo-4-butylsulphanylbenzene 
• 100256-29-9 1-(4-butylsulfanyl-phenyl)-ethanone 
• 73242-21-4 4-(n-butylthio)benzophenone 
• 91428-00-1 1-Phenylsulfonyl-1,1,2-trichlor-pentan 
• 142920-96-5 4-butylthiophenyl phenyl sulfide 
• 882-33-7 diphenyldisulfane 
• 82135-73-7 phenylmethyl-n-butylsulfonium fluoroborate 
• 76447-88-6 S-n-butyl-S-phenyl-N-(ethoxycarbonyl)sulfilimine 
• 72653-47-5 α-chlorobutyl phenyl sulfide 
• 16823-62-4 butyl phenyl sulfone 
• 13153-10-1 (R)-(+)-butyl phenyl sulfoxide 
• 13153-10-1 (S)-(-)-n-butyl phenyl sulfoxide 

Relevant academic research and scientific papers

A highly efficient palladium-catalyzed one-pot synthesis of unsymmetrical aryl alkyl thioethers under mild conditions in water

A palladium-catalyzed, one-pot synthesis of unsymmetrical aryl alkyl thioethers involving aryl halides (aryl bromides and chlorides), thiourea and alkyl bromides has been realized under mild conditions (room temperature to 50 °C) in water with polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile. The PTS/water could be recycled in up to eight runs without an obvious change in its activity. Copyright

Efficient copper(I)-catalyzed C-S cross coupling of thiols with aryl halides in water

CuI efficiently catalyzes the C-S cross coupling of thiols with aryl halides in the presence of tetrabutylammonium bromide in water. The reactions with aryl thiols that have electron-withdrawing and -donating substituents are comparable and afford C-S cross-coupling products in high yield. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Reactivity of a β-diketiminate-supported magnesium alkyl complex toward small molecules

The reactivity of the magnesium alkyl {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(nBu)}2 (1) toward various small molecules provides access to a variety of magnesium derivatives. For example, the insertion of elemental chalcogens (S8 and Se8) into the Mg-C bond of complex 1 gives the dimeric magnesium thiolate {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(μ-SnBu)}2 (2), magnesium selenolate [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(SenBu)(THF) (3), and magnesium diselenolate [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(Se2nBu)(THF) (4). Meanwhile, compound 4 can be readily obtained by further insertion of one selenium atom into complex 3. Moreover, the reactions of complex 1 with diphenyl dichalcogenides (PhSSPh and PhSeSePh) by σ bond metathesis afford the corresponding magnesium phenyl chalcogenolates [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(EPh)(THF) (E = S 5, Se 6) concomitant with PhEnBu release. Furthermore, the treatment of complex 1 with benzonitrile and phenyl isothiocyanate produces the serendipitous magnesium-1-azaallyl complex [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(N(H)C(Ph)CHC3H7)(DME) (7) and the diimino-thioamidato magnesium compound {κ3-N,N′,N′′-(ArNCMe)2[N(Ph)CS]CH}Mg[(Ph)NC(nBu)S] (8) (Ar = 2,6-iPr2C6H3). In addition, deprotonation occurs between compound 1 and 1-methylimidazole to generate the imidazolyl complex {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(μ-Im)}2 (9) (Im = 2-N-methylimidazolyl). These results indicated that the butylmagnesium complex 1 possesses high activity toward small molecules and revealed several unusual transformations. All the new compounds were characterized by various spectroscopic methods, and their solid-state structures were further confirmed by single-crystal X-ray diffraction analyses.

C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.

The effect of inert salts on the structure of the transition state in the SN2 reaction between thiophenoxide ion and butyl chloride

The effect of inert salts on the structure of the transition state has been determined by measuring the secondary α deuterium and the chlorine leaving group kinetic isotope effects for the SN2 reaction between n-butyl chloride and thiophenoxide ion in both methanol and DMSO. The smaller secondary α deuterium isotope effects and very slightly larger chlorine isotope effects found in both solvents when the inert salt is present suggests that the SN2 transition state is tighter and more product-like, with a shorter S - Cα and very a slightly longer Cα - Cl bond when the added salt is present. The salt effect on the reaction in methanol where the reacting nucleophile is the solvent-separated ion-pair complex is much greater than the salt effect on the reaction in DMSO where the reacting nucleophile is the free ion. This greater change in transition-state structure found when the inert salt is present in methanol is consistent with the solvation rule for SN2 reactions. The greater change in the S - Cα bond is predicted by the bond strength hypothesis. A rationale for the changes found in transition-state structure when the inert salt is present is suggested for both the free-ion and the ion-pair reactions.

Nano CoCuFe2O4-catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom-economic and ligand-free route to access unsymmetrical amines and sulfides

An efficient protocol was developed for the nano CoCuFe2O4-catalyzed C-N and C-S bond formation. By this catalytic system, both amine and sulfide-based structural motifs were formed efficiently in aryl halide-free route. The amination reaction of phenyl boronic acid with various types of amines was conducted under ligand-free conditions, in ethanol as a green solvent at 60°C. Unsymmetrical diaryl/aryl alkyl sulfide synthesis via the coupling reaction of arylboronic acids with thiols was also conducted. The nano cobalt-copper ferrite was used as a heterogenous efficient, inexpensive, magnetically separable and recyclable catalyst that can be used for several cycles.

Copper oxide nanoparticles supported on graphene oxide-Catalyzed S-arylation: An efficient and ligand-free synthesis of aryl sulfides

Copper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand-free and solvent-free C-S cross-coupling reactions with weak bases such as tri- ethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade C-S and C-N cross-coupling of ortho-dihalides and ortho-aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E-factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.

The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions

In the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to give the corresponding aryl sulfides in excellent yield.The reaction is useful to prepare symmetrical or unsymmetrical diaryl sulfides and aryl alkyl sulfides.The reaction mechanism does not involve aryl halide radical anions, but is thought to involve oxidative addition of aryl halide to Pd(0), nucleophilic substitution on the adduct followed by reductive elimination.

Reductive cleavage of S-S bond by Zn/AlCl3 system: A novel method for the synthesis of sulfides from alkyl tosylates and disulfides

Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. This thiolate anion species then react with alkyl tosylates to give sulfides in high execellent yields.

Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides

NiCl2·6H2O efficiently catalyzes the C-S bond formation by the cross-coupling of aryl iodides with thiols in tetrabutylammonium bromide (TBAB) in excellent yield. The reaction functions in air and the NiLn-TBAB can be recovered and recycled without the loss of activity.