(4-Methoxy-benzyl)-trimethyl-silane

Base Information

• Chemical Name: (4-Methoxy-benzyl)-trimethyl-silane
• CAS No.: 17988-20-4
• Molecular Formula: C11H18OSi
• Molecular Weight: 194.349
• DSSTox Substance ID: DTXSID10452117
• Nikkaji Number: J450.635I
• Wikidata: Q82272514
• Mol file: 17988-20-4.mol

Synonyms:17988-20-4;(4-methoxy-benzyl)-trimethyl-silane;(4-Methoxybenzyl)trimethylsilane;(4-Methoxybenzyl)-trimethyl-silane;(4-methoxyphenyl)methyl-trimethylsilane;[(4-METHOXYPHENYL)METHYL]TRIMETHYLSILANE;Benzene, 1-methoxy-4-[(trimethylsilyl)methyl]-;SCHEMBL5574984;DTXSID10452117;MFCD08752429;AKOS006289302

Chemical Property of (4-Methoxy-benzyl)-trimethyl-silane

Chemical Property:

• Boiling Point: 235.1 °C at 760 mmHg
• Flash Point: 74.5 °C
• PSA: 9.23000
• Density: 0.903 g/cm³
• LogP: 3.38150
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 194.112691728
• Heavy Atom Count: 13
• Complexity: 143

Purity/Quality:

99% Min ^*data from raw suppliers

(4-METHOXY-BENZYL)-TRIMETHYL-SILANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C[Si](C)(C)C
• General Description: (4-Methoxybenzyl)trimethylsilane is a benzyltrialkylsilane derivative where the phenyl ring is substituted with a 4-methoxy group. According to the literature, the cation radical of (4-METHOXY-BENZYL)-TRIMETHYL-SILANE exhibits a decreased rate constant for nucleophile-assisted C-Si bond cleavage compared to the parent benzyltrimethylsilane, due to the electron-donating nature of the 4-methoxy substituent. This stabilization effect results in longer lifetimes for the cation radical, particularly in less nucleophilic solvents or when trace nucleophiles like water are excluded. The study highlights the influence of electronic and steric factors on the reactivity of benzyltrialkylsilane cation radicals.

Technology Process of (4-Methoxy-benzyl)-trimethyl-silane

There total 27 articles about (4-Methoxy-benzyl)-trimethyl-silane 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%

1-bromo-4-methoxy-benzene (104-92-7) + trimethylsilylmethyllithium (1822-00-0) → (4-methoxy-benzyl)-trimethyl-silane (17988-20-4)

Guidance literature:

1-bromo-4-methoxy-benzene; With bis(tri-t-butylphosphine)palladium⁽⁰⁾; oxygen; In toluene; at 20 ℃; for 0.0166667h; Schlenk technique;

trimethylsilylmethyllithium; In toluene; at 20 ℃; for 0.0333333h; Schlenk technique;

DOI:10.1002/anie.201700417

Reference yield: 95.0%

1-bromo-4-methoxy-benzene (104-92-7) + [scandium tris(trimethylsilylmethyl)(THF)2] (41705-65-1) → (4-methoxy-benzyl)-trimethyl-silane (17988-20-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In toluene; at 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6cc01312k

Reference yield: 89.0%

1-bromo-4-methoxy-benzene (104-92-7) + Lu(trimethylsilylmethyl)3(tetrahydrofuran)2 → (4-methoxy-benzyl)-trimethyl-silane (17988-20-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In toluene; at 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6cc01312k

upstream raw materials:

chloro-trimethyl-silane

4-methoxybenzylmagnesium chloride

p-methoxybenzyl chloride

1-bromo-4-methoxy-benzene

Downstream raw materials:

<(4-Methoxy-1.4-cyclohexadien-1-yl)methyl>trimethylsilan

9-(4-Methoxy-benzyl)-9,10-dihydro-anthracene-9,10-dicarbonitrile

4-(3'-fluorobenzyl)-1-naphtalenedicarbonitrile

4-((trimethylsilyl)methyl)phenol