Methyl 4-(Trimethylsilyl)benzoate

Base Information

• Chemical Name: Methyl 4-(Trimethylsilyl)benzoate
• CAS No.: 22515-30-6
• Molecular Formula: C11H16O2Si
• Molecular Weight: 208.332
• DSSTox Substance ID: DTXSID60447250
• Nikkaji Number: J673.436G
• Wikidata: Q82266094
• Mol file: 22515-30-6.mol

Synonyms:Methyl 4-(Trimethylsilyl)benzoate;22515-30-6;Methyl 4-trimethylsilylbenzoate;C11H16O2Si;SCHEMBL254228;Methyl4-(Trimethylsilyl)benzoate;DTXSID60447250;XAA51530;AC5665;MFCD22682799;AKOS027256915;4-Trimethylsilylbenzoic acid methyl ester;AS-76273;SY022239;CS-0449784;EN300-7471200;A919958

Chemical Property of Methyl 4-(Trimethylsilyl)benzoate

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 208.091956283
• Heavy Atom Count: 14
• Complexity: 200

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 4-(Trimethylsilyl)benzoate

There total 16 articles about Methyl 4-(Trimethylsilyl)benzoate 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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane (574755-28-5) + methyl iodide (74-88-4) → 4-(trimethylsilyl)benzoic acid methyl ester (22515-30-6)

Guidance literature:

di-tert-butyl dicarbonate; (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane; With 4,4'-dimethyl-2,2'-bipyridines; lithium methanolate; copper(l) chloride; In N,N-dimethyl acetamide; at 30 ℃; for 6h; Inert atmosphere; Schlenk technique;

methyl iodide; In N,N-dimethyl acetamide; at 30 ℃; for 2h; Schlenk technique;

DOI:10.1055/a-1377-7369

Reference yield: 91.0%

methyl 4‐(2,2,2‐trifluoroacetyl)benzoate (75748-12-8) → 4-(trimethylsilyl)benzoic acid methyl ester (22515-30-6)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 1,10-Phenanthroline; In toluene; at 160 ℃; for 18h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c00772

Reference yield: 87.0%

4-methoxycarbonylphenyl bromide (619-42-1) + sodium trimethylsilyldimethylsilanolate → 4-(trimethylsilyl)benzoic acid methyl ester (22515-30-6)

Guidance literature:

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

DOI:10.1021/acscatal.1c02733

upstream raw materials:

p-Trimethylsilylbenzoylchlorid

sodium methylate

1-bromo-4-(trimethylsilyl)benzene

carbonic acid dimethyl ester

Downstream raw materials:

5-(4-Trimethylsilanyl-phenyl)-2,3,5,6-tetrahydro-imidazo[2,1-a]isoquinolin-5-ol

C₂₂H₂₃NO₅

methyl 4-(5-bromothiophen-2-yl)benzoate

4,4'-biphenyldicarboxylic acid dimethyl ester