Trimethylsilyl iodide
TRIMETHYLSILYL IODIDE · TMIS · TRIMETHYLIODOSILANE · TMS iodide · CT3610 · IodotrimethyL · Trimethylsilyl io · Iodotrmethylsilane
Identifiers & Physical Properties
| CAS No. | 16029-98-4 |
|---|---|
| Molecular formula | C3H9ISi |
| Average molar mass | 200.09 g/mol |
| Monoisotopic mass | 199.95182482 g/mol |
| SMILES | C[Si](C)(C)I |
| InChIKey | CSRZQMIRAZTJOY-UHFFFAOYSA-N |
| PubChem CID | 85247 |
| EC No. | 240-171-0 |
| DTXSID | DTXSID4065997 |
Chemical & Physical Properties
| Topological polar surface area | 0 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 28.4 |
| Chemical classes | Metals -> Metalloid Compounds (Silicon) |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Physical Description | Clear light brown liquid[Sigma-Aldrich MSDS] |
| Melting point | <0°C |
| Boiling point | 106 °C(lit.) |
| Density | 1.406 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.471(lit.) |
| Flash point | −25 °F |
| Storage conditions | -20°C |
| Solubility | reacts |
| Physical state | Liquid |
| Specific gravity | 1.47 |
| Color | Clear colorless to reddish |
| Sensitivity | Moisture & Light Sensitive |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| BRN | 1731136 |
| Stability | Moisture Sensitive (Reactive) |
| InChI | 1S/C3H9ISi/c1-5(2,3)4/h1-3H3 |
| InChIKey | CSRZQMIRAZTJOY-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)I |
| CAS DataBase Reference | 16029-98-4(CAS DataBase Reference) |
| FDA UNII | 7A65KRZ6NV |
| NIST Chemistry Reference | Iodotrimethylsilane(16029-98-4) |
| EPA Substance Registry System | Silane, iodotrimethyl- (16029-98-4) |
| UNSPSC Code | 12352103 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05 |
| Signal word | Danger |
| GHS hazard statements | H225-H314 |
| GHS precautionary statements | P210-P233-P240-P280-P303+P361+P353-P305+P351+P338 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | F,C |
| Risk statements (R) | 11-14-34 |
| Safety statements (S) | 16-26-36/37/39-43-45-25 |
| UN transport number | UN 2924 3/PG 2 |
| Water hazard class (WGK) | 3 |
| F | 8-21 |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Eye Dam. 1Flam. Liq. 2Skin Corr. 1B |
| Packing group | II |
| Customs code | 29310095 |
| Storage class | 3 - Flammable liquids |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH225 (98.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Silane, iodotrimethyl-Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24465Iodotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Reacts violently with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Sigma-Aldrich MSDS] See Silicon tetraiodide. |
| Hazard Classes and Categories | Flam. Liq. 2 (98.4%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| F | 8-21 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2924 3/PG 2 |
| Customs code | 29310095 |
| Risk statements (R) | 11-14-34 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05 |
| Hazard symbols | F,C |
| Safety statements (S) | 16-26-36/37/39-43-45-25 |
| Hazard class | 3Eye Dam. 1Flam. Liq. 2Skin Corr. 1B |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H225-H314 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P233-P240-P280-P303+P361+P353-P305+P351+P338 |
Applications & Uses
Uses
Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.
General Description
Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.
Preparation & Synthesis
Preparation
Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.