4206-67-1 Usage
Description
(Iodomethyl)trimethylsilane, also known as (Iodomethyl)TMS, is an organosilicon compound with the chemical formula (CH3)3Si-I. It is a clear yellow to brown liquid at room temperature and has a boiling point of 140-142 °C with a density of 1.442 g/cm3. (IODOMETHYL)TRIMETHYLSILANE is known for its reactivity and is widely used in various chemical reactions and synthesis processes.
Uses
Used in Chemical Synthesis:
(Iodomethyl)trimethylsilane is used as a reagent for the N-alkylation of amides, which is an essential step in the preparation of unstabilized ylides for [2+3]-cycloadditions. This application is crucial in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (Iodomethyl)trimethylsilane is used to react with acetoacetic acid ethyl ester, resulting in the formation of 3-trimethylsilanyl-propionic acid ethyl ester. (IODOMETHYL)TRIMETHYLSILANE serves as a key intermediate in the synthesis of various drugs and medicinal compounds.
Used in Organic Chemistry:
(Iodomethyl)trimethylsilane can be employed as an electrophile for the preparation of allylsilanes and propargylsilanes. These organosilicon compounds are valuable building blocks in organic chemistry and are used in the synthesis of natural products, pharmaceuticals, and advanced materials.
Used in Alkene Synthesis:
(IODOMETHYL)TRIMETHYLSILANE forms carbon alkylation adducts that are useful for alkene synthesis. Alkenes are essential components in the chemical industry and are used in the production of various chemicals, plastics, and synthetic rubbers.
Used in Reactive Intermediate Formation:
(Iodomethyl)trimethylsilane readily undergoes metal-halogen exchange, generating a reagent for Peterson methylenation. This reaction is a widely used method for the synthesis of alkenes from carbonyl compounds, which are crucial in the production of various chemicals and pharmaceuticals.
Used in Ylide Precursors:
(IODOMETHYL)TRIMETHYLSILANE also forms nitrogen and sulfur alkylation adducts that function as ylide precursors. Ylides are important intermediates in organic chemistry, particularly in the Wittig reaction, which is used for the synthesis of alkenes and other complex organic molecules.
Purification Methods
If slightly violet in colour, wash it with aqueous 1% sodium metabisulfite, H2O, dry (Na2SO4) it and fractionally distil it at 760mm. [Whitmore & Sommer J Am Chem Soc 68 481 1946, Beilstein 4 IV 3878.]
Check Digit Verification of cas no
The CAS Registry Mumber 4206-67-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,0 and 6 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4206-67:
(6*4)+(5*2)+(4*0)+(3*6)+(2*6)+(1*7)=71
71 % 10 = 1
So 4206-67-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H11ISi/c1-6(2,3)4-5/h4H2,1-3H3
4206-67-1Relevant articles and documents
Schumann,Mueller
, p. C5 (1978)
Hydrocarbon-Soluble Bis(trimethylsilylmethyl)calcium and Calcium-Iodine Exchange Reactions at sp2-Hybrized Carbon Atoms
Koch, Alexander,Wirgenings, Marino,Krieck, Sven,G?rls, Helmar,Pohnert, Georg,Westerhausen, Matthias
, p. 3981 - 3986 (2017/10/31)
Hydrocarbon-soluble and highly reactive [(L)xCa(CH2SiMe3)2] (L = tetrahydropyran, x = 4 (2a); L = tmeda, x = 2 (2b)) is synthesized by the metathesis reaction of Me3SiCH2CaI (1-I) with KCH2SiMe3. The durability of 2a in tetrahydropyran solution at 0 °C is sufficiently high for subsequent chemical transformations. The reaction of ICH2SiMe3 with calcium in diethyl ether yields unique cage compound [(Et2O)2Ca(I)2·(Et2O)2Ca(I)(OEt)·(Et2O)Ca(I)(CH2SiMe3)] (3). We demonstrate that alkylcalcium complexes are valuable reagents for calcium-iodine exchange reactions at Csp2-I functionalities.
1,3-γ-Silyl-elimination in electron-deficient cationic systems
Mercadante, Michael A.,Kelly, Christopher B.,Hamlin, Trevor A.,Delle Chiaie, Kayla R.,Drago, Michael D.,Duffy, Katherine K.,Dumas, Megan T.,Fager, Diana C.,Glod, Bryanna L. C.,Hansen, Katherine E.,Hill, Cameron R.,Leising, Rebecca M.,Lynes, Catherine L.,Macinnis, Allyson E.,McGohey, Madeline R.,Murray, Stephanie A.,Piquette, Marc C.,Roy, Shaina L.,Smith, Ryan M.,Sullivan, Katherine R.,Truong, Bao H.,Vailonis, Kristina M.,Gorbatyuk, Vitaliy,Leadbeater, Nicholas E.,Tilley, Leon J.
, p. 3983 - 3994 (2014/10/15)
Placement of an electron-withdrawing trifluoromethyl group (-CF 3) at a putative cationic centre enhances γ-silyl neighbouring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway is 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation. The scope of this cyclopropanation reaction is explored for numerous cyclic and acyclic examples, proving this method to be a viable approach to preparing CF3-substituted cyclopropanes and bicyclic systems, both containing quaternary centres. Rate-constants, kinetic isotope effects, and quantum mechanical calculations provided evidence for this enhancement and further elaborated the disparity in the reaction outcome between these systems and previously studied γ-silyl systems.
