3385-94-2

Basic information

• Product Name: BIS(TRIMETHYLSILYL) SULFIDE
• Synonyms: 1,1,1,3,3,3-HEXAMETHYLDISILATHIANE;BIS(TRIMETHYLSILYL) SULFIDE;HEXAMETHYLDISILTHIANE;HEXAMETHYLDISILATHIANE;THIOBIS(TRIMETHYLSILANE);Bis(trimethylsilyl)sulfur;Disilathiane,hexamethyl-;Disilthiane, hexamethyl-
• CAS NO: 3385-94-2
• Molecular Formula: C₆H₁₈SSi₂
• Molecular Weight: 178.44
• EINECS: 222-201-4
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Chemical Synthesis;Organometallic Reagents;Organosilicon;Others
• Mol File: 3385-94-2.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 164 °C(lit.)
• Flash Point: 79 °F
• Appearance: Colorless/Liquid
• Density: 0.846 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.25mmHg at 25°C
• Refractive Index: n20/D 1.4586(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with terahydrofuran and toluene.
• Water Solubility: Soluble in tetrahydrofuran and toluene. Hydrolyzes in water.
• Sensitive: Air Sensitive
• Stability: store cold
• BRN: 1740046
• CAS DataBase Reference: BIS(TRIMETHYLSILYL) SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(TRIMETHYLSILYL) SULFIDE(3385-94-2)
• EPA Substance Registry System: BIS(TRIMETHYLSILYL) SULFIDE(3385-94-2)

Safety Data

• Hazard Codes: T
• Statements: 10-23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-13-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 3385-94-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Bis(trimethylsilyl) sulfide is used as a silylating agent in the synthesis of pseudohalides, trifluoroacetate, and tetramethylsilyl halides. It is also used in the transformation of oxides and chlorides into corresponding sulfides, which is crucial for the synthesis of various organic compounds.
Used in the Preparation of Dimethyltrisulfane and Thiones:
Bis(trimethylsilyl) sulfide is used in the preparation of dimethyltrisulfane, a compound used as a vulcanizing agent for rubber and as a flotation agent in the mining industry. Additionally, it is used in the preparation of thiones from aldehydes and ketones, which are important intermediates in organic synthesis.
Used as a Reducing Agent:
Bis(trimethylsilyl) sulfide serves as a reducing agent to reduce aromatic nitro compounds to amines, which are essential building blocks in the synthesis of various pharmaceuticals, dyes, and other organic compounds.
Used in Bis-O-Demethylation:
Hexamethyldisilathiane, another name for bis(trimethylsilyl) sulfide, may be used in the bis-O-demethylation of dimethoxy aromatic compounds, which is an important reaction in the synthesis of various organic compounds.
Used as a Sulfur Source:
Bis(trimethylsilyl) sulfide may be used as a sulfur source in the conversion of amides and lactams to their corresponding sulfur analogs, allyl alcohols to diallyl sulfides, transition metal halides to metal sulfides, and aryl iodides to diaryl sulfides. These conversions are crucial for the synthesis of various sulfur-containing compounds and materials.
Used in Reduction of Oxides:
Bis(trimethylsilyl) sulfide (TMS2S) is used to reduce aromatic nitro groups to amines and the oxides of sulfur, selenium, and tellurium. The conditions for nitro group reduction are forcing, but yields are good. BIS(TRIMETHYLSILYL) SULFIDE is also effective in reducing sulfoxides to sulfides, selenoxides to selenides, and telluroxides to tellurides, with mild conditions that work well on both aliphatic and aromatic oxides.

Purification Methods

Dissolve it in pet ether (b ca 40o), remove the solvent and distil it. Redistil it under atmospheric pressure of dry N2. It is collected as a colourless liquid which solidifies to a white solid in Dry-ice. On standing for several days it turns yellow possibly due to liberation of sulfur. Store it below 4o under dry N2. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4033.]

InChI:InChI=1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 16029-98-4 trimethylsilyl iodide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1825-61-2 Trimethylmethoxysilane 
• 1825-62-3 ethyl trimethylsilyl ether 
• 1825-64-5 isopropoxytrimethylsilane 
• 18146-00-4 allyloxytrimethylsilane 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 18143-79-8 trimethylsilyl propyl sulfide 
• 76275-36-0 3,3-dimethyl-1-trimethylsiloxy-1-trimethylsilylthiobut-1-ene 
• 87729-50-8 C₁₇H₃₂NPSSi₂ 
• 87729-51-9 C₂₂H₃₄NPSSi₂ 
• 17356-08-0 thiourea 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 

Downstream Products

• 18001-91-7 bistrimethyl(1,4-butanedioxy)silane 
• 20836-40-2 bis(2-trimethylsilyloxylethyl)amine 
• 13058-24-7 tert-butoxytrimethylsilane 
• 64248-89-1 C₁₃H₂₆S₂Si₃ 
• 3658-80-8 dimethyltrisulfane 
• 75-77-4 chloro-trimethyl-silane 
• 65197-27-5 1,3-di(trimethylsilthia)-1,1,3,3-tetramethyldisiloxane 
• 18156-36-0 1,1,3,3,5,5-hexamethyl-2,4-dioxa-6-thia-1,3,5-trisilacyclohexane 
• 17865-95-1 2,4,6,8-octamethylcyclotetrasil-1,5-dithia-3,7-dioxane 
• 102105-32-8 1-<(trimethylsilthia)dimethylsiloxy>-1,1-dimethyl-3-<(chloro)dimethylsiloxy>-3,3-dimethyldisilthiane 
• 7677-24-9 trimethylsilyl cyanide 
• 3600-24-6 diethyltrisulfane 
• 125208-51-7 C₅H₁₄O₂SSi 
• 2754-27-0 trimethylsilyl acetate 

Relevant articles and documents

Methods for preparation of disilathianes

Several literature methods for preparation of disilathianes were reexamined and new procedures were developed. Two methods especially useful for the preparation of hexamethyldisilathiane were the reaction between lithium metal, sulfur, and TMS chloride in THF, and the reaction between Li2S and TMS chloride in THF at room temperature. These two procedures may also be used to prepare other hexaalkyldisilathianes. Other methods investigated for the preparation of hexamethyldisilathiane included (a) reaction between commercial anhydrous Na2S and TMS chloride in N,N'-dimethylpropyleneurea or HMPA, (b) production of a highly-reactive Na2S by reaction between sodium dispersion and sulfur, followed by reaction with TMS chloride in THF at room temperature, and (c) reaction between sulfur, NaH, and TMS chloride in N,N'-dimethylpropyleneurea.

Convenient Syntheses of Hexamethyldisilathiane and Tetramethyldisilathiane

Hexamethyldisilathiane and 1,1,3,3-tetramethyldisilathiane are prepared in excellent yields in a one-pot procedure by treating in situ generated disodium sulfide with chlorotrimethylsilane and chlorodimethylsilane, respectively.

Dithiophosphorylation of nerol and geraniol trimethylsilyl derivatives

Reaction of tetraphosphorus decasulfide with О-(cis- and trans-3,7-dimethylocta-2,6-dien-1-yl)-trimethylsilanes affords О,О-bis(cis- and trans-3,7-dimethylocta-2,6-dien-1-yl) S-(trimethylsilyl)dithiophosphates.

Preparation method of hexamethyl disilicon sulfide

The invention discloses a preparation method of hexamethyl disilicon sulfide, wherein the preparation method comprises the following preparation steps: (1) introducing inert gas into a 3000 mL four-mouth flask, adding bulk metal lithium and anhydrous tetrahydrofuran, and reacting; (2) adding sublimed sulfur powder in batches for reaction; (3) after the addition of the sulfur powder is completed, slowly dropwise adding 1270 mL of trimethylchlorosilane for reaction; and (4) after dropwise adding is finished, keeping the temperature at 35-50 DEG C, continuously reacting for 2-4 hours, raising the temperature, carrying out atmospheric distillation to remove a solvent, carrying out reduced pressure distillation to obtain a product with the purity of 90%, collecting the product, and further rectifying to obtain a qualified product with the purity of more than 98%. According to the technical scheme disclosed by the invention, the hexamethyl disilicon sulfide preparation method which is energy-saving, environment-friendly and simple and convenient to operate is realized.

Zinc Tin Chalcogenide Complexes and Their Evaluation as Molecular Precursors for Cu2ZnSnS4 (CZTS) and Cu2ZnSnSe4 (CZTSe)

A series of five heteronuclear zinc tin chalcogenide complexes with the general formula [(tmeda)Zn(SnR2)2E3] (1-R, E = S; R = Me, Ph, tBu; 2-R, E = Se; R = Ph, tBu) have been synthesized and characterized by X-ray crystal structure analysis. In all cases, the six-membered ZnSn2E3 rings exhibit twist boat conformation. The presence of the molecular structures in solution is confirmed by 119Sn and 77Se NMR spectroscopy. Cothermolysis experiments using a mixture of complexes 1-R or 2-R and [(iPr3PCu)2(EC2H4E)]2 as a copper source were monitored by thermogravimetry and temperature dependent X-ray powder diffraction to examine the thermolysis reaction. According to Rietveld refinement, the solid residue consists of Cu2ZnSnS4 (up to 78 wt %) or Cu2ZnSnSe4 (up to 43 wt %) as the main product, respectively.

Facile Construction of Yttrium Pentasulfides from Yttrium Alkyl Precursors: Synthesis, Mechanism, and Reactivity

Treatment of the yttrium dialkyl complex TpMe2Y(CH2Ph)2(THF) (TpMe2 = tri(3,5 dimethylpyrazolyl)borate, THF = tetrahydrofuran) with S8 in a 1:1 molar ratio in THF at room temperature afforded a yttrium pentasulfide TpMe2Y(κ4-S5) (THF) (1) in 93% yield. The yttrium monoalkyl complex TpMe2CpYCH2Ph(THF) reacted with S8 in a 1:0.5 molar ratio under the same conditions to give another yttrium pentasulfide [(TpMe2)2Y]+[Cp2Y(κ4-S5)]? (10) in low yield. Further investigations indicated that the S52- anion facilely turned into the corresponding thioethers or organic disulfides, and released the redundant S8, when it reacted with some electrophilic reagents. The mechanism for the formation of the S52- ligand has been investigated by the controlling of the reaction stoichiometric ratios and the stepwise reactions.

Synthesis and crystal structures of [(iPr3P)2Cu(μ- ESiMe3)(InMe3)] (E = S, Se): Lewis acid-base adducts with chalcogen atoms in planar coordination

The structures of [(iPr3P)2Cu(μ-SSiMe 3)(InMe3)] and [(iPr3P)2Cu(μ- SeSiMe3)(InMe3)] were determined by single-crystal X-ray diffraction. Both complexes are Lewis acid-base adducts of the InMe3 acceptor and the chalcogen donor atom linking a Me3Si group and a (iPr3P)2Cu moiety. They are very unstable under atmospheric conditions and decompose at ambient temperatures. Results of DFT calculations for these complexes and the related hypothetical [(Me 3P)2Cu(μ-SSiMe3)(InMe3)] compound show that the unusual planar coordination of the chalcogen atoms is due to steric crowding. Lewis acid-base adducts of trimethylindium and phosphane-stabilized copper(I) (trimethylsilyl)chalcogenolates were synthesized and characterized by X-ray crystal structure determination. They are very unstable under atmospheric conditions and decompose at ambient temperatures. DFT calculations reveal that the unusual planar coordination of the chalcogen atoms is due to steric crowding. Copyright

Bis(oligosilanyl)chalcogenides [Me3Si)xMe3-xSi]2E, alkalimetal oligosilanylchalcogenolates (Me3Si)xMe3-xSi-EMI and oligosilanylchalcogenols (Me3Si)xMe3-xSi-EH (E = S, Se, Te) syntheses and NMR study

Bis(oligosilanyl)chalcogenides [(Me3Si)x Me3-x Si]2E, alkalimetal oligosilanylchalcogenolates (Me3Si)x Me3-x Si-EMI and oligosilanylchalcogenols (Me3Si)x Me3-x Si-EH (x=1-3; E=S, Se, Te) were synthesized and characterized by 1H-, 13C-, 29Si-, 77Se- and 125Te-NMR spectroscopy. Trends of NMR parameters (chemical shifts, coupling constants) are discussed.

Synthesis of organophosphorus compounds in terms of elemental phosphorus, sulfur and their derivatives

We have developed new facile methods for synthesizing various organophosphorus compouds on the basis of elemental phosphorus and sulfur, phosphorus sulfides and esters of thiophosphorous acids.

New routes to heterocyclic selenium sulfides

New synthetic routes for heterocyclic selenium sulfides are described and the identification of the molecular species by 77Se NMR spectroscopy is discussed. The reaction of [Ti(Me5C5)2S3] and Se2Cl2 produces initially a mixture of 1,2-Se2S6, 1,5-Se2S6 and 1,2,3,4,5-Se5S3 that can be inferred to be formed as a consequence of a rapid decomposition of 1,2-Se2S3. The product distribution is consistent with a series of selenium-atom transfer reactions as well as a dimerization of a four-atomic species that can be thought to be formed in the early stages of the reaction. The treatment of (Me3Si)2Se with Se2S5Cl2 produces initially 1,2,3-Se3S5 and the reaction of (Me3Si)2S and Se2S5Cl2 a mixture of 1,2-Se2S6, 1,5-Se2S6, and SeS7. These products imply that the reactant chloride is a mixture of Cl-Se-S5-Se-Cl and Cl-Se-Se-S4-S-Cl. Upon prolonged standing of all reaction mixtures described above, an equilibrium of several heterocyclic selenium sulfides is formed with the product distribution governed by the molar ratio of sulfur and selenium. The abundance of 77Sc chemical shift data has enabled the quantitative discussion on the trends and has facilitated a more reliable assignment of resonances to different molecular species. Acta Chemica Scandinavica 1998.