Iodotrimethylsilane is used as is an organosilicon compound. It is a colorless, volatile liquid at room temperature.
Product Name Iodotrimethylsilane
Cas No. 16029-98-4
Appearance and properties Colorless Liquid
Storage conditions Stored in normal temperature
Iodotrimethylsilane is used in organic synthesis. A reagent for the division of ethers and esters under neutral conditions.The preparation of trimethylsilenol ether from carbamate to amine, from A, -unsaturated ketone to A – iodosubstituted ketone, from aryl aldehydes to A, a 12-iodosubstituted from -ketone and amidodiester, from alcohol to iodosubstituted from alcohol to hydrolyze the ester;Selective demethylation of methyl ether, methyl linate demethylation, sulfoxide deoxidation, epoxide decomposition.Trimethyl iodosilane (TMSI) is one of the most common reaction agents in organic synthesis
Iodotrimethylsilane has a very wide range of uses.It has many properties and functions that cannot be replaced by other reagents, in particular its ability to selectively and productively break ethers, esters, carbonates, ketones and lactones under extremely mild conditions.The C-O bond of the fractured ether functional group is probably the most important and frequently used chemical function of TMSI.The reaction can be completed in minutes to hours under neutral conditions, and even methyl ether gives good results.The order in which the alkyl group is fractured is: tertiary alkyl > benzyl > allyl > secondary alkyl > primary alkyl (Type 1).Phenolic ethers generally require higher temperatures and longer durations (Type 2).The REACTION of TMSI break esters is much easier than that of other similar reagents, but there are certain differences in the degree of difficulty of the various esters, thus creating an opportunity for selectivity.
The most interesting work in this class of reactions is to use them for the de-protection of multiple carbonate protection groups (Equation 3), for example: select N-BOC or N-CBZ (Type 4).It has also been reported that c-O bond can be broken in phosphate ester in the presence of ether bond.Alcohol hydroxyl can be converted to iodine in a variety of ways, but the mild and efficient conditions under which TMSI is used give it an important place in sugar chemistry.TMSI converts the hydroxyl of acetal in sugar molecules to iodine in a highly selective manner while keeping the other functional groups unchanged (5).Excessive TMSI reaction with a cyclic ether compound is another very valuable reaction for obtaining iodide.Sometimes the iodide produced in this way can be used directly for the next alkylation without separation (Type 6).Although TMSI readily converts alcohols to the corresponding trimethylsilether, or carbonyl groups to the corresponding enols (Formula 7), but due to the reasons of TMSI operation and price, it can be completely replaced by other cheap and convenient reagents.
Iodotrimethylsilane was produced by the followings:
1. Add 5.6g (0.21mol) aluminum powder and 16.2g (0.10mol) hexamethyldissiloxane into the reactor and replace the air with nitrogen.Heat to 60℃, add 50.8g (0.2mol) iodine under stirring, and heat to 140℃ reflux for 1.5h.Atmospheric distillation, 32.6-35.3g trimethyl iodosilane, yield 82-88%.
2. In a 20 ml bottle with reflux condenser, 0.3 g (2 mmol) hxyldiane and 0.5 g (2 mmol > iodine are heated to about 65℃.An exothermic reaction occurs to form a homogeneous solution.Reflux of 1.5 hours, that is, the quantitative formation of trimethyl iodosilane.
In a solution of 4.5 g (30 mmol) anhydrous sodium iodide and 25 ml dry ethyl alcohol, 1.63 g (15 mmol) trimethyl chlorosilane was added under agitation and nitrogen protection.Backflow.
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