Disilathiane, hexamethyl-

Base Information

• Chemical Name: Disilathiane, hexamethyl-
• CAS No.: 3385-94-2
• Molecular Formula: C6H18SSi2
• Molecular Weight: 178.446
• Hs Code.: 29319090
• European Community (EC) Number: 222-201-4
• NSC Number: 252160
• UNII: AZ6L5QJY5H
• DSSTox Substance ID: DTXSID2063006
• Nikkaji Number: J205.475B
• Wikipedia: Bis(trimethylsilyl)sulfide
• Wikidata: Q4917167
• Mol file: 3385-94-2.mol

Synonyms:3385-94-2;Bis(trimethylsilyl) sulfide;Disilathiane, hexamethyl-;Hexamethyldisilathiane;Bis(trimethylsilyl)sulfide;Hexamethyldisilthiane;1,1,1,3,3,3-Hexamethyldisilathiane;Disilthiane, hexamethyl-;trimethyl(trimethylsilylsulfanyl)silane;AZ6L5QJY5H;Disilathiane, 1,1,1,3,3,3-hexamethyl-;EINECS 222-201-4;NSC 252160;NSC-252160;MFCD00014851;NSC252160;Thiobis(trimethylsilane);UNII-AZ6L5QJY5H;C6H18SSi2;Hexamethyldisilathiane, purum;SCHEMBL19477;C6-H18-S-Si2;DTXSID2063006;Bis(Trimethylsilyl)Sulfide, 98%;AKOS015840062;Hexamethyldisilathiane, synthesis grade;1,1,1,3,3,3-hexamethyl-disilathiane;trimethyl[(trimethylsilyl)sulfanyl]silane;1,1,1,3,3,3-Hexamethyldisilathiane #;AS-48160;S([Si](C)(C)C)[Si](C)(C)C;FT-0693392;H0871;F19541;A854553;Q4917167

Chemical Property of Disilathiane, hexamethyl-

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 3.25mmHg at 25°C
• Refractive Index: n20/D 1.4586(lit.)
• Boiling Point: 159.4 °C at 760 mmHg
• Flash Point: 50.2 °C
• PSA: 25.30000
• Density: 0.837 g/cm³
• LogP: 3.38940
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: Miscible with terahydrofuran and toluene.
• Water Solubility.: Soluble in tetrahydrofuran and toluene. Hydrolyzes in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 178.06677482
• Heavy Atom Count: 9
• Complexity: 76.2

Purity/Quality:

97% ^*data from raw suppliers

Bis(trimethylsilyl) Sulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)S[Si](C)(C)C
• Physical properties: bp 164°C; d 0.846 g cm?3.
• Uses: 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. 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. 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.

Technology Process of Disilathiane, hexamethyl-

There total 35 articles about Disilathiane, hexamethyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(isobutylthio)trimethylsilane (78635-72-0) → hexamethyldisilathiane (3385-94-2) + C11H27PS4Si (153080-51-4)

Guidance literature:

With tetraphosphorus decasulfide; at 50 ℃; for 7h;

Reference yield: 95.0%

chloro-trimethyl-silane (75-77-4) → hexamethyldisilathiane (3385-94-2)

Guidance literature:

With sodium sulfide; In tetrahydrofuran; 1.) 0 deg C, 1.5 h, 2.) room temp., 4.5 h;

DOI:10.1055/s-1989-27235

Reference yield: 95.0%

trimethylsilyl propyl sulfide (18143-79-8) → hexamethyldisilathiane (3385-94-2) + Dipropyl-S-trimethylsilyl tetrathiophosphate (146038-45-1)

Guidance literature:

With tetraphosphorus decasulfide; at 20 ℃; for 3h;

DOI:10.1007/BF00864364

upstream raw materials:

chloro-trimethyl-silane

trimethylsilyl iodide

carbon disulfide

lithium bis(trimethylsilyl)phosphide

Downstream raw materials:

trimethylsilyl cyanide

bistrimethyl(1,4-butanedioxy)silane

tris((trimethylsiloxy)methyl)propane

2,2',2''-tris(trimethylsiloxy)triethylamine

Refernces

A direct and stereospecific approach to the synthesis of α-glycosyl thiols

10.1039/b804536d

The study presents a novel and direct method for the synthesis of α-glycosyl thiols, which are compounds of significant interest in biological research and potential therapeutic applications due to their resistance to chemical and enzymatic hydrolysis. The researchers used 1,6-anhydrosugars as the starting materials and bis(trimethylsilyl)sulfide as the sulfur nucleophile, along with catalytic amounts of TMSOTf (trimethylsilyl trifluoromethanesulfonate) to facilitate the ring-opening reaction. This approach resulted in the formation of α-glycosyl thiols in high yields and with excellent stereospecificity, which is crucial for maintaining the desired anomeric configuration in the final thioglycoside products. The purpose of these chemicals was to develop a more efficient and stereoselective synthesis method for α-glycosyl thiols, which are key building blocks for constructing thioglycosides and have applications in the synthesis of various glycoconjugates.

Tris(trimethylsilyl)sulfonium and Methylbis(trimethylsilyl)sulfonium Ions: Preparation, NMR Spectroscopy, and Theoretical Studies

10.1021/jo001248+

The research focuses on the preparation, NMR spectroscopy, and theoretical studies of tris(trimethylsilyl)sulfonium and methylbis(trimethylsilyl)sulfonium ions. These ions were prepared as long-lived species through reactions involving trimethylsilane, trityl tetrakis(pentafluorophenyl)borate (Ph3C+ TPFPB), and precursor sulfides such as hexamethyldisilathiane and methylthiotrimethylsilane. The resulting ions were characterized using 1H, 13C, and 29Si NMR spectroscopy at -78 °C. The study also attempted the synthesis of dimethyl(trimethylsilyl)sulfonium ion but was unsuccessful due to the formation of the more stable trimethylsulfonium ion. The structures and NMR chemical shifts of the ions were calculated using density functional theory (DFT) and IGLO methods, with results aligning well with experimental data.