Iodotrimethylsilane

Base Information

• Chemical Name: Iodotrimethylsilane
• CAS No.: 16029-98-4
• Molecular Formula: C3H9ISi
• Molecular Weight: 200.094
• Hs Code.: 29310095
• European Community (EC) Number: 240-171-0
• UNII: 7A65KRZ6NV
• DSSTox Substance ID: DTXSID4065997
• Nikkaji Number: J150.775C
• Wikipedia: Trimethylsilyl_iodide
• Wikidata: Q1191741
• Mol file: 16029-98-4.mol

Synonyms:iodotrimethylsilane

Chemical Property of Iodotrimethylsilane

Chemical Property:

• Appearance/Colour: Straw liquid
• Vapor Pressure: 40.5mmHg at 25°C
• Melting Point: <0°C
• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 101.5 °C at 760 mmHg
• Flash Point: 15.2 °C
• PSA: 0.00000
• Density: 1.508 g/cm³
• LogP: 2.25630
• Storage Temp.: −20°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: reacts
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 199.95182
• Heavy Atom Count: 5
• Complexity: 28.4

Purity/Quality:

99% ^*data from raw suppliers

Iodotrimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-14-34
• Safety Statements: 16-26-36/37/39-43-45-25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)I
• 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.

Technology Process of Iodotrimethylsilane

There total 69 articles about Iodotrimethylsilane 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: 85.0%

tetrakis(trimethylsiloxy)phosphonium iodide (53380-41-9) → trimethylsilyl iodide (16029-98-4) + Tris(trimethylsilyl) phosphate (10497-05-9)

Guidance literature:

In benzene; Heating; during 5 h the solvent was distilled off, the temp. rose to 110 deg C;

Reference yield: 61.0%

octamethylcyclotetrasiloxane (556-67-2) → tetramethylsilane (75-76-3) + trimethylsilyl iodide (16029-98-4) + Hexamethyldisiloxane (107-46-0) + dodecamethyl-cyclohexasiloxane (540-97-6)

Guidance literature:

With gallium(III) iodide; at 140 - 170 ℃; for 5h; Yield given; Title compound not separated from byproducts;

Reference yield: 61.0%

octamethylcyclotetrasiloxane (556-67-2) → tetramethylsilane (75-76-3) + trimethylsilyl iodide (16029-98-4) + Hexamethyldisiloxane (107-46-0) + hexadecamethylheptasiloxane (541-01-5)

Guidance literature:

With gallium(III) iodide; at 140 - 170 ℃; for 5h; Yield given; Title compound not separated from byproducts;

upstream raw materials:

1,1,1,2,2,2-hexamethyldisilane

me3Si(pr-2-J)

Hexamethyldisiloxane

trimethylphenylsilane

Downstream raw materials:

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

6-iodo-3,3-dimethyl-hexa-1,4-diyne

1-iodo-2-trimethylsilyloxy-ethane

1,4-Diiodobutane

Refernces

• 1、 Abel,E.W. et al.. "-". . p. 2455 - 2458. Retrieved 1964.
• 2、 Walsh,Wells. "". . . Retrieved 1976.
• 3、 Schmidt, Arthur H.,Russ, Manuel. "Element-organische Verbindungen; 8. Verbesserte Herstellung von Bromo- und Iodotrimethylsilan". . p. 67 - 68. Retrieved 1981.
• 4、 Sommer, L. H.,Tyler, L. J.,Whitmore, F. C.. "". . p. 2872 - 2874. Retrieved 1948.
• 5、 Hollwedel, Femke,Khan, Ayesha,Maus, Ulrich A.,Stocker, Bridget L.,Timmer, Mattie S. M.. "Synthesis of α-Glucosyl Diacylglycerides as potential adjuvants for Streptococcus pneumoniae vaccines". . . Retrieved 2020.
• 6、 Friedrich, Edwin C.,Lucca, George de. "HALOGEN REDISTRIBUTION REACTIONS BETWEEN ALKYL HALIDES AND TRIMETHYLSILYL IODIDE". . p. 143 - 148. Retrieved 1982.
• 7、 Tewari, Neera,Rai, Bishwa Prakash,Nizar, Hashim,Singh, Shailendra Kumar. "Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate". . p. 211 - 214. Retrieved 2006.
• 8、 Cartlidge, Ashleigh J.,Matthews, Peter D.. "Indium(III) promoted oxidative P-P coupling of silylphosphines". supporting information. . Retrieved 2022/01/28.