6485-79-6 Usage
Description
Triisopropylsilane is a clear colorless liquid that is a very sterically-hindered silane. It is known for its bulky isopropyl groups which allow for more selective reductions without diminishing their activity. This characteristic makes it a valuable compound in various chemical reactions and applications.
Uses
Used in Chemical Synthesis:
Triisopropylsilane is used as a reducing agent for the selective reduction of anomeric C-phenyl ketals, such as in the copper triflate catalyzed reductive etherification of trimethylsilyl ethers. Its bulky isopropyl groups enable more selective reductions, making it a preferred choice in certain chemical reactions.
Used in Peptide Synthesis:
In the pharmaceutical industry, Triisopropylsilane serves as a protecting group in peptide synthesis. Its steric hindrance allows for the selective protection of certain functional groups during the synthesis process, which is crucial for the successful assembly of peptide sequences.
Used in Silylation Reactions:
Triisopropylsilane is utilized in the selective silylation of primary hydroxyl groups in the presence of secondary alcohols. This selective silylation is important for the synthesis of various organic compounds and can be applied in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Preparation of Anti-1,2-diols:
Triisopropylsilane is employed in the preparation of anti-1,2-diols with high diastereoselectivity, catalyzed by a Ni(O) N-heterocyclic carbine complex. This application is significant in the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of drugs with fewer side effects.
Used as a Cation Scavenger:
In the field of organic chemistry, Triisopropylsilane is used as a cation scavenger in the deprotection of peptides. Its ability to selectively interact with cations helps in the controlled removal of protecting groups, which is a critical step in peptide synthesis and related research.
Check Digit Verification of cas no
The CAS Registry Mumber 6485-79-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,8 and 5 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6485-79:
(6*6)+(5*4)+(4*8)+(3*5)+(2*7)+(1*9)=126
126 % 10 = 6
So 6485-79-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H22Si/c1-7(2)10(8(3)4)9(5)6/h7-10H,1-6H3
6485-79-6Relevant articles and documents
The Triisopropylsilyl Group as a Hydroxyl-Protecting Function
Cunico, Robert F.,Bedell, Lewis
, p. 4797 - 4798 (1980)
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Bypassing a highly unstable frustrated Lewis pair: Dihydrogen cleavage by a thermally robust silylium-phosphine adduct
Herrington, Thomas J.,Ward, Bryan J.,Doyle, Laurence R.,McDermott, Joe,White, Andrew J. P.,Hunt, Patricia A.,Ashley, Andrew E.
, p. 12753 - 12756 (2015/05/20)
The thermally robust silylium complex [iPr3Si-PtBu3]+[B(C6F5)4]- (1) activates H2/D2 at 90 °C (PhCl); no evidence for dissociation into the separated Lewis pair is found. DFT calculations show H2 cleavage proceeds via Si-P bond elongation to form an encounter complex directly from the adduct, thus avoiding the non-isolable iPr3Si+-PtBu3 FLP. This journal is
Versatile method for introduction of bulky substituents to alkoxychlorosilanes
Masaoka, Shin,Banno, Tadashi,Ishikawa, Mitsuo
, p. 182 - 192 (2007/10/03)
The reactions of various alkoxytrichlorosilanes prepared in situ from tetrachlorosilane and alcohols, with Grignard reagents bearing a bulky substituent such as the isopropyl, sec-butyl, and cyclohexyl group afforded triisopropyl-, tri(sec-butyl)-, and tricyclohexylalkoxysilane in high yields. The reactions of n-butoxytrichlorosilane with these Grignard reagents produced triisopropyl-, tri(sec-butyl)-, and tricyclohexyl(n-butoxy)silane in 94%, 96%, and 92% yields, respectively. Methoxymethyldichlorosilane reacted with the same Grignard reagents to give diisopropyl-, di(sec-butyl)-, and dicyclohexylmethoxymethylsilane in 84%, 83%, and 83% yields. Treatment of methoxydimethylchlorosilane with the Grignard reagents readily afforded isopropyl-, sec-butyl-, and cyclohexylmethoxydimethylsilane in excellent yields. Similar treatment of methoxydimethylchlorosilane with tert-butylmagnesium chloride gave tert-butylmethoxydimethylsilane in 62% yield.