2-Trimethylsilyl-1,3-dithiane
2-TRIMETHYLSILYL-1,3-DITHIANE · 1,3-DITHIAN-2-YLTRIMETHYLSILANE · 1,3-Dithiane-2-yltrimethylsilane · 2-TRIMETHYLSILYL-1,3-DITHIANE 97% · 1,3-Dithiane, 2-(trimethylsilyl)- · 2-Trimethylsilyl-1,3-dithiane,97% · Silane, 1,3-dithian-2-yltrimethyl- · 2-Trimethylsilyl-1,3-dithiane, 98+%
Identifiers & Physical Properties
| CAS No. | 13411-42-2 |
|---|---|
| Molecular formula | C7H16S2Si |
| Average molar mass | 192.4 g/mol |
| Monoisotopic mass | 192.04626904 g/mol |
| SMILES | C[Si](C)(C)C1SCCCS1 |
| InChIKey | BTTUMVHWIAXYPJ-UHFFFAOYSA-N |
| PubChem CID | 83413 |
| EC No. | 236-504-4 |
| DTXSID | DTXSID70158542 |
Chemical & Physical Properties
| Topological polar surface area | 50.6 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 103 |
| SpringerMaterials Properties | Chemical shift |
| Boiling point | 54-55 °C0.17 mm Hg(lit.) |
| Density | 1.014 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.533(lit.) |
| Flash point | 205 °F |
| Storage conditions | 2-8°C |
| Solubility | Insol H2Osol organic solvents. |
| Physical state | clear liquid |
| Color | Colorless to Light yellow to Light orange |
| Specific gravity | 1.014 |
| Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions |
| BRN | 1616463 |
| InChI | 1S/C7H16S2Si/c1-10(2,3)7-8-5-4-6-9-7/h7H,4-6H2,1-3H3 |
| InChIKey | BTTUMVHWIAXYPJ-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)C1SCCCS1 |
| CAS DataBase Reference | 13411-42-2(CAS DataBase Reference) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Safety statements (S) | 23-24/25 |
| UN transport number | 3334 |
| Water hazard class (WGK) | 3 |
| F | 13 |
| TSCA inventory status | No |
| Customs code | 2934.99.9001 |
| Storage class | 10 - Combustible liquids |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 13 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | No |
| UN transport number | 3334 |
| Customs code | 2934.99.9001 |
| Safety statements (S) | 23-24/25 |
| Storage class | 10 - Combustible liquids |
Applications & Uses
Uses
A versatile acyl anion equivalent.1,2
Uses
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.
General Description
2-(Trimethylsilyl)-1,3-dithiane participates in Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines. It undergoes novel diazo transfer reaction with tosyl azide in hexamethylphosphoramide-THF to yield 2-diazo-1,3-dithiane, which on decomposition yields formal carbene adducts. It is a versatile acyl anion equivalent.
Preparation & Synthesis
Preparation
2-Trimethylsilyl-1,3-dithiane is prepared by alkylation of 2-lithio-1,3- dithiane with chlorotrimethylsilane (eq 1).