Trimethylsilyl methanesulfonate

Base Information

• Chemical Name: Trimethylsilyl methanesulfonate
• CAS No.: 10090-05-8
• Molecular Formula: C4H12O3SSi
• Molecular Weight: 168.289
• Hs Code.: 2931900090
• European Community (EC) Number: 233-220-2
• DSSTox Substance ID: DTXSID70905831
• Nikkaji Number: J241.261F
• Wikidata: Q72514503
• Mol file: 10090-05-8.mol

Synonyms:TMS-MS;trimethylsilylmethanesulfonate

Chemical Property of Trimethylsilyl methanesulfonate

Chemical Property:

• Vapor Pressure: 0.287mmHg at 25°C
• Melting Point: 103-104 °C
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 209.8 °C at 760 mmHg
• Flash Point: 66.7 °C
• PSA: 51.75000
• Density: 1.067 g/cm³
• LogP: 1.87830
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.02764195
• Heavy Atom Count: 9
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

(Trimethylsilyl)methanesulfonate ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)OS(=O)(=O)C
• Uses: Reactant or reagent involved in:Reduction of esters to ethers using boron difluoride triflate etherateElimination of C(8)-functional groups via regioselective dehydrationDealkylsilylation of alumazene derivatives

Technology Process of Trimethylsilyl methanesulfonate

There total 24 articles about Trimethylsilyl methanesulfonate 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: 98.0%

trimethylsilylazide (4648-54-8) + acetone oxime methanesulfonate (86921-62-2) → 1,5-dimethyl-1H-tetrazole (5144-11-6) + trimethylsilyl methanesulfonate (10090-05-8)

Guidance literature:

In chlorobenzene; for 24h; Heating;

DOI:10.1246/bcsj.58.2419

Reference yield: 96.5%

Methyl methanesulfonate (66-27-3) + trimethylsilyl bromide (2857-97-8) → methyl bromide (74-83-9) + trimethylsilyl methanesulfonate (10090-05-8)

Guidance literature:

for 6h; Heating;

Reference yield: 94.0%

tert-Butylphosphonic bis(trimethylsilyl ester) (97730-12-6) + Methanesulfonic anhydride (7143-01-3) → trimethylsilyl methanesulfonate (10090-05-8) + O,O'-bis(methylsulfonyl)-tert-butylphosphonic acid (97730-11-5)

Guidance literature:

In dichloromethane; for 12h; Ambient temperature;

upstream raw materials:

Methyl methanesulfonate

trimethylsilyl iodide

chloro-trimethyl-silane

methanesulfonic acid

Downstream raw materials:

tetramethylsilane

p-(trimethylsilyl)toluene

(2-methylphenyl)trimethylsilane

diborane

Refernces

• 1、 Nishiyama, Kozaburo,Miyata, Izumi. "Reaction of Trimethylsilyl Azide with C=N-O Bond". . p. 2419 - 2420. Retrieved 1985.
• 2、 Baukov, Yu. I.,Kramarova, E. P.,Negrebetsky, Vad. V.,Shagina, A. D.,Shipov, A. G.,Tarasenko, D. V.. "N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates". . . Retrieved 2020.
• 3、 Tanwar, Lalita,B?rgel, Jonas,Ritter, Tobias. "Synthesis of Benzylic Alcohols by C-H Oxidation". supporting information. p. 17983 - 17988. Retrieved 2019/11/14.
• 4、 Wang, Ming Wen,Chen, Yong Jun,Wang, Dong. "Catalytic allylation of aldehydes with allyltrimethylsilane using in situ-generated trimethylsilyl methanesulfonate (TMSOMs) as a catalyst". . p. 385 - 387. Retrieved 2007/10/03.