(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% ^*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

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-(3'-fluorobenzyl)-1-naphtalenedicarbonitrile

4-((trimethylsilyl)methyl)phenol

p-Methoxybenzyl bromide

p-methylanizole

Refernces

• 1、 Agata, Ryosuke,Takaya, Hikaru,Matsuda, Hiroshi,Nakatani, Naoki,Takeuchi, Katsuhiko,Iwamoto, Takahiro,Hatakeyama, Takuji,Nakamura, Masaharu. "Iron-catalyzed cross coupling of aryl chlorides with alkyl Grignard reagents: Synthetic scope and FeII/FeIV mechanism supported by x-ray absorption spectroscopy and density functional theory calculations". supporting information. p. 381 - 390. Retrieved 2019/02/25.
• 2、 Keaveney, Sinead T.,Kundu, Gourab,Schoenebeck, Franziska. "Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer". supporting information. p. 12573 - 12577. Retrieved 2018/09/18.