2-Trimethylsilyl-1,3-dithiane

Base Information

• Chemical Name: 2-Trimethylsilyl-1,3-dithiane
• CAS No.: 13411-42-2
• Molecular Formula: C7H16S2Si
• Molecular Weight: 192.422
• Hs Code.: 2934999090
• European Community (EC) Number: 236-504-4
• DSSTox Substance ID: DTXSID70158542
• Nikkaji Number: J317.864A
• Wikidata: Q83026812
• Mol file: 13411-42-2.mol

Synonyms:2-Trimethylsilyl-1,3-dithiane;13411-42-2;(1,3-dithian-2-yl)trimethylsilane;1,3-Dithian-2-yl(trimethyl)silane;1,3-Dithian-2-yltrimethylsilane;Silane, 1,3-dithian-2-yltrimethyl-;2-(Trimethylsilyl)-1,3-dithiane;C7H16S2Si;EINECS 236-504-4;[1,3]dithian-2-yl-trimethyl-silane;MFCD00006655;SCHEMBL279647;2-trimethylsily-1,3-dithiane;2-Trimethylsilyl-13-Dithiane;C7-H16-S2-Si;2-trimethylsilyl-1, 3-dithiane;2-(trimethysilyl)-1,3-dithiane;DTXSID70158542;(1,3-dithiane-2-yl)trimethyl silane;AKOS015840136;1,3-Dithian-2-yl(trimethyl)silane #;FS-5760;s19325;AC-30987;2-(Trimethylsilyl)-1,3-dithiane, >=99%;CS-0130866;FT-0608984;FT-0660841;T1514;D95288;J-006486

Chemical Property of 2-Trimethylsilyl-1,3-dithiane

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.0185mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Boiling Point: 261.7 °C at 760 mmHg
• Flash Point: 96.1 °C
• PSA: 50.60000
• Density: 1.01 g/cm³
• LogP: 3.47990
• Storage Temp.: 2-8°C
• Solubility.: Insol H2O; sol organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 192.04626939
• Heavy Atom Count: 10
• Complexity: 103

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Trimethylsilyl-1,3-dithiane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Canonical SMILES: C[Si](C)(C)C1SCCCS1
• Physical properties: bp 54–55 °C/0.17 mmHg.
• Uses: A versatile acyl anion equivalent.1,2 2-Trimethylsilyl-1,3-dithiane is the precursor of dithioketene acetals which are good substrates for both cationic and anionic cyclization processes; the anion reacts with unsaturated ketones and aldehydes to give vinyl dithioketene acetals that can be used as dienes or for the preparation of substituted α,β-unsaturated alkyl ketones; alkylation of the anion provides a general synthesis of acylsilanes. It participates the following reactions: Thioketene Acetals, Cationic and Anionic Cyclizations, Unsaturated Dithioketene Acetals, Acylsilanes, Multicomponent Linchpin Reactions, Formation of Bis(acylsilanes) etc.

Technology Process of 2-Trimethylsilyl-1,3-dithiane

There total 5 articles about 2-Trimethylsilyl-1,3-dithiane 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: 89.0%

1,3 dithiane (505-23-7) + chloro-trimethyl-silane (75-77-4) → 2-(trimethylsilyl)-1,3-dithiane (13411-42-2)

Guidance literature:

1,3 dithiane; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201501185

Reference yield: 84.0%

chloro-trimethyl-silane (75-77-4) + 2-lithio-1,3-dithiane (36049-90-8) → 2-(trimethylsilyl)-1,3-dithiane (13411-42-2)

Guidance literature:

In tetrahydrofuran; hexane; -78 deg C to room t.;

Reference yield:

1,3 dithiane (505-23-7) + 1-bromo-2-methyl-1-trimethylsilylpropene (65426-00-8) → 2-(trimethylsilyl)-1,3-dithiane (13411-42-2) + 1-(1,3-Dithian-2-yl)-2-methyl-1-trimethylsilyl-1-propen (97513-20-7)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -20 deg C, 2.5 h; 2.) THF, room temp., 10 h;

upstream raw materials:

1,3 dithiane

chloro-trimethyl-silane

1-bromo-2-methyl-1-trimethylsilylpropene

2-lithio-1,3-dithiane

Downstream raw materials:

3-(2-trimethylsilyl-1,3-dithian-2-yl)cyclohexanone

1-(2-Trimethylsilanyl-[1,3]dithian-2-yl)-cyclohex-2-enol

2-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl-methylene)-1,3-dithian

2-Cyclohex-3-enylmethylene-[1,3]dithiane

Refernces

• 1、 Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro. "Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification". supporting information. p. 116 - 120. Retrieved 2018/12/05.
• 2、 Murakami, Kei,Imoto, Junichi,Matsubara, Hiroshi,Yoshida, Suguru,Yorimitsu, Hideki,Oshima, Koichiro. "Copper-catalyzed extended pummerer reactions of ketene dithioacetal monoxides with alkynyl sulfides and ynamides with an accompanying oxygen rearrangement". supporting information. p. 5625 - 5630. Retrieved 2013/06/26.