tert-Butoxychlorodiphenylsilane

Base Information

• Chemical Name: tert-Butoxychlorodiphenylsilane
• CAS No.: 17922-24-6
• Molecular Formula: C16H19ClOSi
• Molecular Weight: 290.865
• Hs Code.: 29319090
• European Community (EC) Number: 626-967-4
• DSSTox Substance ID: DTXSID60370857
• Nikkaji Number: J254.909C
• Wikidata: Q82158012
• Mol file: 17922-24-6.mol

Synonyms:tert-Butoxychlorodiphenylsilane;17922-24-6;tert-Butoxy(chloro)diphenylsilane;chloro-[(2-methylpropan-2-yl)oxy]-diphenylsilane;tert-Butoxydiphenylchlorosilane;Benzene, 1,1'-[chloro(1,1-dimethylethoxy)silylene]bis-;t-butoxydiphenylsilyl chloride;SCHEMBL766008;Benzene,1,1'-[chloro(1,1-dimethylethoxy)silylene]bis-;tert-Butoxydiphenylsilyl Chloride;DTXSID60370857;BBL102587;MFCD00077672;STL556390;AKOS005255036;FS-3988;B1436;FT-0637626;T70450;A812436;J-011434;tert-Butoxy(chloro)diphenylsilane, >=97.0% (GC);chloranyl-[(2-methylpropan-2-yl)oxy]-diphenyl-silane;TERT-BUTOXYDIPHENYLCHLOROSILANE (STABILIZED WITH CACO3)

Chemical Property of tert-Butoxychlorodiphenylsilane

Chemical Property:

• Refractive Index: n20/D 1.539
• Boiling Point: 331 °C at 760 mmHg
• Flash Point: 128.2 °C
• PSA: 9.23000
• Density: 1.07 g/cm³
• LogP: 3.29690
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 290.0893695
• Heavy Atom Count: 19
• Complexity: 257

Purity/Quality:

98% ^*data from raw suppliers

tert-Butoxydiphenylchlorosilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)O[Si](C1=CC=CC=C1)(C2=CC=CC=C2)Cl
• General Description: TERT-BUTOXYCHLORODIPHENYLSILANE, also known as tert-butoxydiphenylsilyl chloride, is a reagent used for the protection of alcohols as tert-butoxydiphenylsilyl (TBDPS) ethers. These protecting groups demonstrate high hydrolytic stability and enhanced reactivity toward fluoride ions, enabling selective deprotection in the presence of other silyl ethers. They are particularly useful for protecting primary alcohols and can be employed in synthetic transformations where controlled fluoride-mediated cleavage is desired. The TBDPS group offers a balance of acid resistance and fluoride sensitivity, making it a valuable tool in organic synthesis for selective alcohol protection and deprotection strategies.

Technology Process of tert-Butoxychlorodiphenylsilane

There total 1 articles about tert-Butoxychlorodiphenylsilane 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: 89.0%

diphenylsilyl dichloride (80-10-4) + tert-butyl alcohol (75-65-0) → tert-butyloxydiphenylsilyl chloride (17922-24-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 32h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.5b03008

Reference yield: 100.0%

tert-butyloxydiphenylsilyl chloride (17922-24-6) + (2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol (177568-10-4) → (2R,3R,4R)-1-tert-butyl-diphenylsilyloxy-2,4-dimethyl-5-(phenylthio)pentan-3-ol

Guidance literature:

tert-butyloxydiphenylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

(2R,3R,4R)-2,4-dimethyl-5-(phenylthio)pentane-1,3-diol; In N,N-dimethyl-formamide; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1246/bcsj.20140271

Reference yield: 99.0%

4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-yn-1-ol (856410-65-6) + tert-butyloxydiphenylsilyl chloride (17922-24-6) → tert-butoxy-(4-{6-[3-(4-methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynyloxy)-diphenyl-silane (856410-46-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200500029

upstream raw materials:

diphenylsilyl dichloride

tert-butyl alcohol

Downstream raw materials:

2-octyl-tert-butoxydiphenylsilyl ether

3-(tert-Butoxy-diphenyl-silanyloxymethyl)-heptan-4-ol

tert-Butoxy-dodecyloxy-diphenyl-silane

1-methylcyclohexyl tert-butoxydiphenylsilyl ether

Refernces

Symmetrical Alkoxysilyl Ethers. A New Class of Alcohol-Protecting Groups. Preparation of tert-Butoxydiphenylsilyl Ethers

10.1021/jo00246a038

The research explores the development and evaluation of a new class of alcohol-protecting groups, specifically the alkoxydiphenylsilyl ethers, with a focus on tert-butoxydiphenylsilyl ethers. The purpose of this study was to identify a protecting group that offers both acid stability and high fluoride reactivity, which can be selectively cleaved or retained in the presence of other silyl ethers. The key chemicals used in the research include tert-butoxydiphenylsilyl chloride, various alcohols (such as n-dodecanol, 2-octanol, and 1-methylcyclohexanol), triethylamine, and tetra-n-butylammonium fluoride. The study found that tert-butoxydiphenylsilyl ethers exhibit excellent hydrolytic stability and enhanced fluoride reactivity, making them useful for protecting primary alcohols and for selective deprotection in the presence of other silyl ethers. The research concludes that these ethers are a valuable addition to the existing repertoire of silyl protecting groups, particularly when fluoride sensitivity is desired, and they offer advantages such as selective protection of primary alcohols and compatibility with a wide range of synthetic transformations.

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