110-06-5

Usage

Chemical Properties

clear pale yellow to yellow liquid

Uses

Different sources of media describe the Uses of 110-06-5 differently. You can refer to the following data:
1. Di-tert-butyl disulfide is used in the preparation of gold-supported thin film from symmetrical and mixed disulphide adsorbates. Mechanism of the oxidation of di-tert-butyl disulfide in the presence of H2O2 catalyzed by bis(acetylacetonato)oxovanadium and a chiral Schiff-base ligand has been investigated. Di-tert-butyl disulfide has been used in the preparation of gold-supported thin film from symmetrical and mixed disulphide adsorbates.
2. Di-tert-Butyl Disulfide is a general reagent used in the synthesis of a novel neuropeptide Y (NPY) Y5 receptor antagonist Velneperit) used in the treatment of obesity.

Synthesis Reference(s)

Synthetic Communications, 13, p. 611, 1983 DOI: 10.1080/00397918308059536Synthesis, p. 669, 1978 DOI: 10.1055/s-1978-24844Tetrahedron Letters, 31, p. 3591, 1990 DOI: 10.1016/S0040-4039(00)94450-2

General Description

Mechanism of the oxidation of di-tert-butyl disulfide in the presence of H2O2 catalyzed by bis(acetylacetonato)oxovanadium and a chiral Schiff-base ligand has been investigated.

InChI:InChI=1/C8H18S2/c1-7(2,3)9-10-8(4,5)6/h1-6H3

Upstream product

• 15459-95-7 t-butyl thionitrite 
• 25558-08-1 tert-butylsulfenyl iodide 
• 29364-29-2 sodium tert-butyl thiolate 
• 75-66-1 2-methylpropan-2-thiol 
• 82166-21-0 methyl cyclohexane 
• 115-11-7 isobutene 
• 68048-41-9 tert-Butyl thionitrate 
• 999-90-6 S-tert-butyl thioacetate 
• 13686-74-3 Di-tert-butyl dithiosulfite 
• 75272-63-8 selenium(II) bis(2-methyl-2-propanethiolate) 
• 79306-31-3 1-bromo-2,2-dimethylcyclopropyl methyl sulfide 
• 123-30-8 4-amino-phenol 
• 86254-76-4 1-((Z)-2-tert-Butylsulfanyl-vinyl)-cyclohexanol 
• 86254-75-3 (Z)-1-tert-Butylsulfanyl-3,7-dimethyl-octa-1,6-dien-3-ol 

Downstream Products

• 4253-90-1 di-tert-butyl trisulfide 
• 4151-69-3 tert-butyl ethyl disulfide 
• 43022-60-2 tert-butyl isopropyl disulfide 
• 37850-75-2 allyl tert-butyl sulfide 
• 31172-01-7 acetyl t-butyl disulfide 
• 66236-75-7 C₁₈H₂₁S 
• 35166-82-6 Methyl-tert-butyldisulfid 
• 2406-25-9 di-tert-butyl nitroxide 
• 3084-50-2 tri-n-butylphosphine sulfide 
• 1205-08-9 methyl hippurate 
• 258505-90-7 (+/-)-dimethyl-2,3-dibenzamidobutanedioate 
• 144978-22-3 N-benzoyl-α-t-butylthioglycine methyl ester 
• 2848-29-5 bis(2-phenylethenyl) sulfide 
• 42442-47-7 (E)-1-phenyl-2-(tert-butylthio)ethene 

Relevant academic research and scientific papers

Thermal rearrangement of terf-butylsulfinamide

tert-Butylsulfinamides are unstable above room temperature, and in chlorinated solvents they undergo rearrangement to form the more stable N-(tert-butylthio)-tert-butylsulfonamide.

A rapid and efficient synthesis of symmetrical disulfides under microwave irradiation conditions

A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.

The Titanium Dioxide Sensitised Photo-Oxidation of Sulphides

Titanium dioxide has been shown to photosensitise the oxidation of sulphides to give sulphoxides and sulphones.Evidence is presented against the involvement of singlet oxygen and in favour of the sulphide radical cations as being intermediates.

Reactivity of Nucleophiles toward and the Site of Nucleophilic Attack on Bis(alkylthio) Selenides

Bis(alkylthio)selenides, RSSeSR (1), a class of compounds that occupy a key role as intermediates in the incorporation of inorganic selenium into biological systems, react quite readily with nucleophilic reagents.In principle, such reactions could take place at either sulfur (eq 3a) or at selenium (eq 3b).In the present work the reaction of a series of 1 having R groups of varying steric dimensions (n-Bu, i-Pr, t-Bu) with a group of common nucleophiles (thiolate, cyanide, and sulfite ions, phenyllithium, piperidine) has been examined.The results show that when R = t-Bu, reaction with the nucleophile at selenium occurs considerably faster than reaction at sulfur, but that when R is an n-alkyl group (n-Bu), reaction at sulfur is considerably faster than reaction at selenium.With R = i-Pr, the rates of reaction at the two sites are comparable.For reaction at sulfur, the retardation in rate accompanying a change in R from n-Bu to i-Pr to t-Bu parallels closely the decrease in rate with the same change in R that has been observed in other nucleophilic substitution at dicoordinate sulfur.As might be expected, an increase in steric dimensions of R has a considerably smaller effect on the rate of mechanism at selenium.Comparison of the rate of reaction of n-BuS- with n-BuSSeSBu-n and n-BuSSBu-n shows that bis(n-alkylthio) selenides can be expected generally to be more than several orders of magnitude more reactive toward nucleophiles than the corresponding disulfide.

Synthesis and decomposition of some dialkyl oxide derivatives of organotrisulfides

The isolation or detection of sulfenic sulfonic thioanhydrides 1 (e.g., 6), sulfenyl vic-disulfoxides 4 (e.g., 9, 14), and sulfinic thioanhydrides 5 (e.g., 20) has been carried out by oxidative procedures at various temperatures. The decomposition of these compounds has been investigated and is shown to be consistent with the mechanism proposed for the decomposition of trisulfide monoxides.

Metal-free air oxidation of thiols in recyclable ionic liquid: A simple and efficient method for the synthesis of disulfides

An efficient procedure for the oxidative coupling of alkyl, aryl and heteroaryl thiols with atmospheric oxygen is reported. The methodology utilizes BMIM-BF4 as a recyclable solvent and does not require support materials or metal salts. Symmetric disulfides are obtained in excellent yields.

The rapid and efficient synthesis of disulfides from alkyl and acyl halides

Various symmetrical dialkyl and diacyl disulfides are prepared easily in high yields from the corresponding alkyl and acyl halides under mild and nonaqueous conditions using N,N'-dibutyl-N,N,N',N'-tetramethyl- ethylenediammonium tetrahydroborate (BTMETB) or N,N'-dibenzyl-N,N,N',N'- tetramethylethylenediammonium tetrahydroborate (BZTMETB) and elemental sulfur. The quaternary diammonium borohydrides were easily prepared by treatment of the corresponding quaternary diammonium chloride or bromide with alkaline solution of sodium borohydride at room temperature.

Oxidation of thiols to disulfides with monochloro poly(styrenehydantoin) beads

Various thiols were converted to symmetrical disulfides. This facile and reproducible method uses water as a solvent, and monochloro poly(styrenehydantoin) beads as an oxidizing agent.

CATALYTIC OXIDATION OF THIOLS BY COENZYME PQQ

Oxidation of thiols by coenzyme PQQ as a new enzymatic oxidation-reduction model was found to proceed catalytically under aerobic conditions to give corresponding disulfides.

REACTION OF SULFUR DIOXIDE WITH THIOLS CATALYZED BY BORON TRIFLUORIDE ETHERATE. EVIDENCE FOR A POSSIBLE INTERVENTION OF DITHIOSULFITE AS A REACTION INTERMEDIATE.

The reaction of sulfur dioxide (SO//2) with 1-propanethiol (NPT), 2-propanethiol (IPT), or 2-methyl-2-propanethiol (TBT) catalyzed by boron trifluoride ethrate (BF//3OEt//2) was investigated. The ratios of dialkyl trisulfide to dialkyl disulfide obtained (RSSSR/RSSR) at an early stage of the reaction were larger than 1 for the reaction of TBT and less than 1 for the reaction of NPT or IPT. The reaction of dithiosulfites with BF//3OEt//2 in the presence or absence of thiol was investigated. From a consideration of the similarity of the composition of the sulfides formed in the reaction of dithiosulfites with BF//3OEt//2 to those in the reaction of SO//2 witn thiol in the presence of BF//3OEt//2, the possibility of the intervention of dithiosulfite as a reaction intermediate in the reaction of SO//2 with thiol is discussed.