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

Chemical Properties

clear colorless to slightly yellow liquid

Physical properties

bp 164°C; d 0.846 g cm?3.

Uses

Different sources of media describe the Uses of 3385-94-2 differently. You can refer to the following data:
1. Bis(trimethylsilyl)sulfide is used as a silylating agent in the synthesis of pseudohalides, trifluoroacetate and tetramethylsilyl halides. It is used in the transformation of oxides and chlorides into corresponding sulfides. It is also used in the preparation of dimethyltrisulfane as well as thiones from aldehydes and ketones. Further, it is used as a reducing agent to reduce aromatic nitro compounds to amines.
2. Hexamethyldisilathiane may be used in the bis-O-demethylation of dimethoxy aromatic compounds. It may also be used as a sulfur source in the following conversion: Amides and lactams to their corresponding sulfur analogs.Allyl alcohols to diallyl sulfides. Transition metal halides to metal sulfides.Aryl iodides to diaryl sulfides.
3. Bis(trimethylsilyl) sulfide (TMS2S) is used to reduce aromatic nitro groups to amines and the oxides of sulfur, selenium, and tellurium. Conditions for nitro group reduction (eq 1) are forcing; however, yields are good. Reactions of TMS2S with primary aliphatic nitro groups result in the formation of the thiohydroxamic acids (eq 2) which can be isolated or carried further to the nitrile. Secondary alkyl nitro derivatives provide oximes. Sulfoxides are reduced to sulfides, selenoxides to selenides, and telluroxides to tellurides. Conditions are mild and work well on both the 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 
• 75-15-0 carbon disulfide 
• 59624-91-8 lithium bis(trimethylsilyl)phosphide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 18146-00-4 allyloxytrimethylsilane 
• 17887-80-8 1,3-bis(trimethylsiloxy)propane 
• 5573-62-6 (ethylthio)trimethylsilane 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 98351-27-0 C₂₀H₅₄S₄Si₆ 
• 17356-08-0 thiourea 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 463-58-1 carbon oxide sulfide 

Downstream Products

• 3232-39-1 acetyl sulfide 
• 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 
• 2290-65-5 trimethylsilyl isothiocyanate 

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.

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.

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.