3-(Trimethylsilyl)anisole

Base Information

• Chemical Name: 3-(Trimethylsilyl)anisole
• CAS No.: 17876-90-3
• Molecular Formula: C10H16OSi
• Molecular Weight: 180.322
• Hs Code.: 29310099
• DSSTox Substance ID: DTXSID90375370
• Nikkaji Number: J502.263K
• Wikidata: Q82163901
• Mol file: 17876-90-3.mol

Synonyms:3-(Trimethylsilyl)anisole;17876-90-3;(3-methoxyphenyl)-trimethylsilane;3-Methoxyphenyltrimethylsilane;(3-methoxyphenyl)trimethylsilane;Benzene, 1-methoxy-3-(trimethylsilyl)-;Benzene,1-methoxy-3-(trimethylsilyl)-;3-trimethylsilylanisole;SCHEMBL9843250;trimethyl(3-methoxyphenyl)silane;DTXSID90375370;AKOS015910624

Chemical Property of 3-(Trimethylsilyl)anisole

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Boiling Point: 208.8 °C at 760 mmHg
• Flash Point: 60.8 °C
• PSA: 9.23000
• Density: 0.91 g/cm³
• LogP: 2.24040
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 180.097041664
• Heavy Atom Count: 12
• Complexity: 139

Purity/Quality:

98%Min ^*data from raw suppliers

3-(TRIMETHYLSILYL)ANISOLE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC=C1)[Si](C)(C)C

Technology Process of 3-(Trimethylsilyl)anisole

There total 49 articles about 3-(Trimethylsilyl)anisole 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: 91.0%

N,N-diethyl-2-methoxy-4-trimethylsilanyl-benzenesulfonamide → 3-trimethylsilylanisol (17876-90-3)

Guidance literature:

With bis(acetylacetonate)nickel(II); diisopropylmagnesium; In diethyl ether; at 20 ℃;

DOI:10.1002/anie.200352633

Reference yield: 85.0%

chloro-trimethyl-silane (75-77-4) + 1-chloro-3-methoxy-benzene (2845-89-8) → 3-trimethylsilylanisol (17876-90-3)

Guidance literature:

With magnesium; sodium iodide; In tetrahydrofuran; at 25 ℃; for 10h; Glovebox; Inert atmosphere;

Reference yield: 81.0%

3-methoxyphenyl bromide (2398-37-0) + sodium trimethylsilyldimethylsilanolate → 3-trimethylsilylanisol (17876-90-3)

Guidance literature:

With MePhos Pd G₄; In 1,2-dichloro-ethane; at 50 ℃;

DOI:10.1021/acscatal.1c02733

upstream raw materials:

chloro-trimethyl-silane

1-chloro-3-methoxy-benzene

(3-methoxyphenyl)magnesium bromide

3-methoxyphenyl bromide

Downstream raw materials:

2-chloro-5-methoxyphenyltrimethylsilane

methoxybenzene

1-methoxy-3-nitrosobenzene

3,3'-dimethoxybiphenyl

Refernces

• 1、 Hitoshio, Kenshiro,Yamagishi, Hiroki,Shimokawa, Jun,Yorimitsu, Hideki. "Sodium silylsilanolate enables nickel-catalysed silylation of aryl chlorides". supporting information. p. 6867 - 6870. Retrieved 2021/07/19.
• 2、 Liu, Luo-Yan,Qiao, Jennifer X.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan. "Meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity". supporting information. p. 14870 - 14877. Retrieved 2019/10/02.