ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Silane > Iodotrimethylsilane
Iodotrimethylsilane Chemical Properties
- Melting point:<0°C
- Boiling point:106 °C(lit.)
- Density 1.406 g/mL at 25 °C(lit.)
- refractive index n
- Flash point:−25 °F
- storage temp. −20°C
- solubility reacts
- form Liquid
- color Clear colorless to reddish
- Specific Gravity1.47
- Water Solubility reacts
- Sensitive Moisture & Light Sensitive
- Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
- BRN 1731136
- CAS DataBase Reference16029-98-4(CAS DataBase Reference)
- NIST Chemistry ReferenceIodotrimethylsilane(16029-98-4)
- EPA Substance Registry SystemSilane, iodotrimethyl- (16029-98-4)
Iodotrimethylsilane Usage And Synthesis
- DescriptionIodotrimethylsilane which has a hard acid (Me3Si) -soft base (I) bond displays a strong oxygenophilicity towards ethers, esters, lactones, acetals, and other molecules involving oxygen atom as a functional group.
The use of iodotrimethylsilane as the agent brought about a facile cleavage of the tert-butyl ester, giving the corresponding carboxylic acid in excellent yield.
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.
Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.
For the introduction of the TMS group, e.g., TMS enol ethers.
Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.
- UsesTrimethylsilyliodide is a typical blocking agent in pharmaceutical manufacturing, widely used in the syntheses of drugs. It can protect or deprotect functional groups selectively, act as silane blocking agent.
- PreparationIodotrimethylsilane, prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes.
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.
- Chemical PropertiesStraw liquid
- UsesIodotrimethylsilane is an efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage.
- ReactionsTrimethylsilyl iodide reacts under mild conditions in the absence of a catalyst with alkyl fluorides as well as with benzyl and tertiary alkyl chlorides and bromides to give good yields of alkyl iodides and the corresponding trimethylsilyl halides.
- Chemical SynthesisA 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60° as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140° to 210°, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°.
- Purification MethodsAdd a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]
Iodotrimethylsilane Preparation Products And Raw materials
- N-(Trimethylsilyl)acetamide Trimethylsilyl cyanide Iodotrimethylsilane Trimethoxysilane tert-Butyldimethylsilyl chloride Methyltris(methylethylketoxime)silane Methyltriacetoxysilane TRIMETHYLSILANE Bromotrimethylsilane 3-Chloropropyltrimethoxysilane Vinyltrimethoxysilane Propidium iodide Isobutyltrimethoxysilane Potassium iodide Azidotrimethylsilane Tetramethylsilane SILANE COUPLING AGENT Phenyltrimethoxysilane
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