Tert-butyl[(4-iodophenyl)methoxy]dimethylsilane

Base Information

• Chemical Name: Tert-butyl[(4-iodophenyl)methoxy]dimethylsilane
• CAS No.: 147283-96-3
• Molecular Formula: C13H21IOSi
• Molecular Weight: 348.299
• European Community (EC) Number: 822-585-9
• Mol file: 147283-96-3.mol

Synonyms:tert-butyl[(4-iodophenyl)methoxy]dimethylsilane;147283-96-3;tert-butyl-[(4-iodophenyl)methoxy]-dimethylsilane;tert-Butyl((4-iodobenzyl)oxy)dimethylsilane;tert-butyl[(4-iodobenzyl)oxy]dimethylsilane;SCHEMBL3012099;4-Iodobenzyl alcohol, TBDMS derivative;Tert-butyl(4-iodobenzyloxy)dimethylsilane;EN300-203369;4-Iodobenzyl alcohol, tert-butyldimethylsilyl ether;A1-36347

Chemical Property of Tert-butyl[(4-iodophenyl)methoxy]dimethylsilane

Chemical Property:

• PSA: 9.23000
• LogP: 4.81300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 348.04064
• Heavy Atom Count: 16
• Complexity: 215

Purity/Quality:

tert-butyl[(4-iodophenyl)methoxy]dimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1=CC=C(C=C1)I

Technology Process of Tert-butyl[(4-iodophenyl)methoxy]dimethylsilane

There total 8 articles about Tert-butyl[(4-iodophenyl)methoxy]dimethylsilane 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: 100.0%

4-iodo-benzyl alcohol (18282-51-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-(tert-butyldimethylsiloxymethyl)iodobenzene (147283-96-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1.75h;

DOI:10.1016/j.bmcl.2012.05.012

Reference yield:

1H-imidazole (288-32-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,3-bis(1,1-dimethylethyl)-1,1,3,3-tetramethyldisiloxane (67875-55-2) + 4-(tert-butyldimethylsiloxymethyl)iodobenzene (147283-96-3)

Guidance literature:

In N-methyl-acetamide;

Reference yield:

4-iodobenzoic acid (619-58-9) → 4-(tert-butyldimethylsiloxymethyl)iodobenzene (147283-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride, DMF / toluene / 1 h / Ambient temperature

2: LiCl, NaBH₄ / 1,2-dimethoxy-ethane / 1 h

3: 97.7 percent / (4-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

With dmap; sodium tetrahydroborate; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; lithium chloride; In 1,2-dimethoxyethane; dichloromethane; toluene;

DOI:10.1002/jlcr.2580340303

upstream raw materials:

4-iodo-benzyl alcohol

tert-butyldimethylsilyl chloride

4-iodobenzoic acid

1.4-dibromobenzene

Downstream raw materials:

[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-(4-iodo-phenyl)-methanol

4-allyloxy-1-[(tert-butyl(dimethyl)silyloxy)methyl]benzene

dimethyl 4-(tert-butyldimethylsiloxymethyl)phenylphosphonate

[2-(4-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)ethynyl]trimethylsilane