Bromotrimethylsilane

Base Information

• Chemical Name: Bromotrimethylsilane
• CAS No.: 2857-97-8
• Molecular Formula: C3H9BrSi
• Molecular Weight: 153.094
• Hs Code.: 29310095
• European Community (EC) Number: 220-672-0
• NSC Number: 139857
• UNII: JHH5G299BX
• DSSTox Substance ID: DTXSID1062671
• Nikkaji Number: J150.732J
• Wikidata: Q62455523
• Mol file: 2857-97-8.mol

Synonyms:NSC 139857;Trimethylbromosilane;Trimethylsilicon bromide;Trimethylsilylbromide;Silane,bromotrimethyl-;

Chemical Property of Bromotrimethylsilane

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 100mmHg at 25°C
• Melting Point: -43 °C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 79 °C at 760 mmHg
• Flash Point: 90 °F
• PSA: 0.00000
• Density: 1.205 g/cm³
• LogP: 2.21620
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: DECOMPOSES
• Water Solubility.: DECOMPOSES
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 151.96569
• Heavy Atom Count: 5
• Complexity: 28.4

Purity/Quality:

99% ^*data from raw suppliers

Bromotrimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-34-29-14
• Safety Statements: 16-26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)Br
• Uses: Bromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs. Bromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15). Adefovir intermediate Powerful silylating agent
• Physical properties: bp 79°C; d 1.188 g cm?3; n20 D 1.4240; fp 32°C.

Technology Process of Bromotrimethylsilane

There total 177 articles about Bromotrimethylsilane 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: 93.0%

phenyl trimethylsilyl selenide (33861-17-5) → trimethylsilyl bromide (2857-97-8) + diphenyl diselenide (1666-13-3)

Guidance literature:

With bromine; at 0 ℃;

DOI:10.1021/jo00320a012

Reference yield: 86.0%

Hexamethyldisiloxane (107-46-0) → trimethylsilyl bromide (2857-97-8)

Guidance literature:

With aluminum tri-bromide; In neat (no solvent); heating of (CH3)3SiOSi(CH3)3 and AlBr3;;

Reference yield: 80.0%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) → trimethylsilyl bromide (2857-97-8)

Guidance literature:

With bromine; at 0 ℃;

DOI:10.1021/jo00158a018

upstream raw materials:

methyl bromide

dimethyldibromosilane

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

trimethylsilan

Downstream raw materials:

1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane

1-bromo-4-((trimethylsilyl)oxy)butane

3-Brompropionsaeure-O-trimethylsilylester

diethyl trimethylsilyl phosphite

Refernces

• 1、 Kosanovich, Alex J.,Shih, Wei-Chun,Ramírez-Contreras, Rodrigo,Ozerov, Oleg. V.. "N-H cleavage as a route to new pincer complexes of high-valent rhenium". . p. 18532 - 18540. Retrieved 2016.
• 2、 Gilliam,Meals,Sauer. "-". . p. 1161. Retrieved 1946.
• 3、 Sakurai, Hideki,Sasaki, Koshi,Hosomi, Akira. "STEPWISE CONVERSION OF OXIRANES TO ALLYLIC ALCOHOLS BY IODOTRIMETHYLSILANE AND DBU". . p. 2329 - 2332. Retrieved 1980.
• 4、 Pitcher, Michael W.,Bianconi, Patricia A.. "A simple one-pot synthesis of methyltribromosilane". . p. 1819 - 1822. Retrieved 2007.
• 5、 Rakhlin,Podgorbunskaya,Voronkov. "Homolytic reactions of N-bromohexamethyldisilazane with trialkyl(phenylalkoxy) derivatives of silicon and tin". experimental part. p. 930 - 935. Retrieved 2011/01/09.