Allyltriisopropylsilane

Base Information

• Chemical Name: Allyltriisopropylsilane
• CAS No.: 24400-84-8
• Molecular Formula: C12H26Si
• Molecular Weight: 198.424
• European Community (EC) Number: 625-488-8
• DSSTox Substance ID: DTXSID60407556
• Nikkaji Number: J684.951B
• Wikidata: Q72437425
• Mol file: 24400-84-8.mol

Synonyms:Allyltriisopropylsilane;24400-84-8;tri(propan-2-yl)-prop-2-enylsilane;C12H26Si;Allyltriisopropylsilane, 98%;AKQHUJRZKBYZLC-UHFFFAOYSA-;DTXSID60407556;AKQHUJRZKBYZLC-UHFFFAOYSA-N;MFCD00075115;AKOS015838908;A1858;CS-0158033;S00400;T70632;InChI=1/C12H26Si/c1-8-9-13(10(2)3,11(4)5)12(6)7/h8,10-12H,1,9H2,2-7H3

Chemical Property of Allyltriisopropylsilane

Chemical Property:

• Appearance/Colour: colorless transparent liquid
• Vapor Pressure: 0.274mmHg at 25°C
• Melting Point: < 0 °C
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 210.7 °C at 760 mmHg
• Flash Point: 76.1 °C
• PSA: 0.00000
• Density: 0.767 g/cm³
• LogP: 4.85120
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 198.180377364
• Heavy Atom Count: 13
• Complexity: 135

Purity/Quality:

99.5% ^*data from raw suppliers

Allyltriisopropylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)[Si](CC=C)(C(C)C)C(C)C
• General Description: Allyltriisopropylsilane is an allylsilane compound used as a substrate in rhodium-catalyzed C–H bond arylation reactions, where it undergoes functionalization with iodoarenes to form arylated products. Its reactivity in such transformations highlights its utility as a nucleophilic alkene in synthetic chemistry, particularly in metal-catalyzed processes involving C–H activation. The presence of triisopropylsilyl groups contributes to its stability and influences its reactivity in these catalytic systems.

Technology Process of Allyltriisopropylsilane

There total 5 articles about Allyltriisopropylsilane 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%

triisopropylsilyl chloride (13154-24-0) + allyl bromide (106-95-6) → allyl triisopropylsilane (24400-84-8)

Guidance literature:

allyl bromide; With magnesium; In diethyl ether; at 20 ℃; for 16h; Inert atmosphere; Reflux;

triisopropylsilyl chloride; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol4028978

Reference yield: 96.0%

allylmagnesium bromide (2622-05-1) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → allyl triisopropylsilane (24400-84-8)

Guidance literature:

In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)98211-X

Reference yield: 94.0%

triisopropylsilyl chloride (13154-24-0) + allylmagnesium bromide (1730-25-2) → allyl triisopropylsilane (24400-84-8)

Guidance literature:

triisopropylsilyl chloride; allylmagnesium bromide; In tetrahydrofuran; at 55 ℃; for 15h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2015.05.007

upstream raw materials:

allylmagnesium bromide

triisopropylsilyl trifluoromethanesulfonate

triisopropylsilyl chloride

3-chloroprop-1-ene

Downstream raw materials:

[2-Chloro-4-(4-methoxy-phenyl)-4-phenyl-butyl]-triisopropyl-silane

4-allylbenzonitrile

ethyl 2-hydroxy-2-phenyl-4-pentanoate

Refernces

Arylation of allylsilanes through rhodium catalysis

10.1246/cl.2009.186

The research investigates a new method for the C–H bond arylation of allylsilanes using a rhodium complex as a catalyst. The primary purpose of this study is to develop a novel protocol for the functionalization of C–H bonds in allylsilanes, which could open up new strategies in chemical synthesis. The key chemicals used in the research include allyltriisopropylsilane as the substrate, RhCl(CO){P[OCH(CF3)2]3}2 as the rhodium catalyst, Ag2CO3 as the additive, and various iodoarenes as the arylating agents. The reactions are carried out in m-xylene at 120°C. The study concludes that the rhodium-catalyzed system effectively promotes the arylation of allylsilanes with iodoarenes, producing the desired products in moderate yields. The research also highlights the importance of the P[OCH(CF3)2]3 ligand and silver-based additives in the reaction mechanism. Although improvements in efficiency and selectivity are needed, the findings represent a promising starting point for the functionalization of nucleophilic alkenes and pave the way for further exploration in this area of C–H bond activation.