(Iodomethyl)trimethylsilane

Base Information

• Chemical Name: (Iodomethyl)trimethylsilane
• CAS No.: 4206-67-1
• Molecular Formula: C4H11ISi
• Molecular Weight: 214.121
• Hs Code.: 29319090
• European Community (EC) Number: 224-123-6
• DSSTox Substance ID: DTXSID70194900
• Nikkaji Number: J46.444I
• Wikidata: Q63395530
• Mol file: 4206-67-1.mol

Synonyms:(Iodomethyl)trimethylsilane;4206-67-1;Iodomethyltrimethylsilane;iodomethyl(trimethyl)silane;C4H11ISi;(Trimethylsilyl)methyl iodide;iodomethyl-trimethylsilane;EINECS 224-123-6;iodomethyl-trimethyl-silane;trimethylsilyl methyl iodide;iodanylmethyl(trimethyl)silane;SCHEMBL279623;C4-H11-I-Si;VZNYXGQMDSRJAL-UHFFFAOYSA-;DTXSID70194900;(Iodomethyl)trimethylsilane, 99%;AMY42187;MFCD00001077;AKOS015909290;AB88246;FS-5413;CS-0067163;FT-0627267;I0449;(Iodomethyl)trimethylsilane, >=99.0% (GC);D73359;EN300-708743;A825746;Q-200021;Q63395530

Chemical Property of (Iodomethyl)trimethylsilane

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 7.81mmHg at 25°C
• Melting Point: 137-141 °C
• Refractive Index: n20/D 1.491(lit.)
• Boiling Point: 140 °C at 760 mmHg
• Flash Point: 31.8 °C
• PSA: 0.00000
• Density: 1.436 g/cm³
• LogP: 2.71710
• Storage Temp.: Flammables area
• Sensitive.: Light Sensitive
• Solubility.: Difficult to mix.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 213.96747
• Heavy Atom Count: 6
• Complexity: 37.3

Purity/Quality:

99% ^*data from raw suppliers

(Iodomethyl)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-24/25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CI
• Physical properties: bp 140–142 °C; d 1.442 g cm?3.
• Uses: (Iodomethyl)trimethylsilane is used for the N-alkylation of amides, in a reaction sequence to prepare unstabilized ylides for [2+3]-cycloadditions. It can react with acetoacetic acid ethyl ester to get 3-trimethylsilanyl-proπonic acid ethyl ester. (Iodomethyl)trimethylsilane can be used as electrophile for the preparation of allylsilanes and propargylsilanes; forms carbon alkylation adducts useful for alkene synthesis; alkylation adducts are frequently a source of fluorideinduced reactive intermediates, forming nitrogen and sulfur alkylation adducts that function as ylide precursors; readily undergoes metal–halogen exchange to generate a reagent for Peterson methylenation.

Technology Process of (Iodomethyl)trimethylsilane

There total 16 articles about (Iodomethyl)trimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Chloromethyltrimethylsilane (2344-80-1) → iodo(trimethylsilyl)methane (4206-67-1)

Guidance literature:

With sodium iodide; In acetone; for 24h; Ambient temperature; in the dark;

Reference yield: 70.0%

sodium iodide (7681-82-5,24359-64-6,41927-88-2,115813-40-6) + Chloromethyltrimethylsilane (2344-80-1) → iodo(trimethylsilyl)methane (4206-67-1)

Guidance literature:

In not given;

DOI:10.1021/ja01207a036

Reference yield: 65.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + trimethylsilyl iodide (16029-98-4) → iodo(trimethylsilyl)methane (4206-67-1)

Guidance literature:

In diethyl ether; at -78 ℃; for 1h;

DOI:10.1055/s-1988-27554

upstream raw materials:

methyl magnesium iodide

(chloromethyl)trichlorosilane

Chloromethyltrimethylsilane

diazomethane

Downstream raw materials:

[1-Phenyl-meth-(E)-ylidene]-(1-phenyl-2-trimethylsilanyl-ethyl)-amine

1-iodo-butane

Chloromethyltrimethylsilane

1-((E)-2-((trifluoromethyl)sulfonyl)vinyl)benzene

Refernces

• 1、 Yue, Fuyang,Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin. "Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator". supporting information. p. 7306 - 7310. Retrieved 2021/10/01.
• 2、 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.. "1,3-γ-Silyl-elimination in electron-deficient cationic systems". . p. 3983 - 3994. Retrieved 2014/10/15.