18163-47-8 Usage
Description
1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97, also known as (Iodoethynyl)trimethylsilane, is an organic compound with the molecular formula C5H8ISi. It is a colorless liquid at room temperature and is widely used as an alkyne coupling reagent in various chemical reactions. The compound is characterized by its physical properties, including a boiling point of 96 °C at standard atmospheric pressure, a refractive index of 1.5110 at 20°C, and a density of 1.46 g/cm3.
Uses
1. Chemical Synthesis:
1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 is used as an alkyne coupling reagent in chemical synthesis, predominantly in conjunction with organocopper species or palladium catalysis. It is particularly effective in aryland vinylcopper coupling reactions, where it serves well due to the lack of reactivity of alkynyl moieties bound to copper in reverse procedures.
2. Research Applications:
In the field of research, 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 may be used to investigate the reactivity of diamagnetic cobalt(I) complexes, such as Tol-BDI((2-pp)2)Co [Tol-BDI((2-pp)2)H = 2-(4-tolyl)-1,3-bis(2-isopropylpyridyl)propenediimine]. This application helps researchers understand the behavior and properties of these complexes, which can be useful in various chemical and materials science applications.
3. Synthesis of Complex Molecules:
1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 can be used for the synthesis of complex organic molecules, such as 1-(4-trimethylsilanylbuta-1,3-diynyl)pyrene, via Pd-coupling with 1-iodo-2-trimethylsilylacetylene. This synthesis is important in the development of new materials with specific properties and applications in various industries, including pharmaceuticals, electronics, and materials science.
Used in Pharmaceutical Industry:
1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those with potential applications in the treatment of various diseases and conditions. Its unique chemical properties make it a valuable building block in the development of new drugs and therapeutic agents.
Used in Electronics Industry:
In the electronics industry, 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 may be used in the development of advanced materials with specific electronic properties, such as semiconductors, conductors, or insulators. These materials can be used in the manufacturing of electronic devices, components, and systems, contributing to the advancement of technology and innovation in this field.
Used in Materials Science:
1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 can be employed in the synthesis of novel materials with unique properties, such as high strength, lightweight, or thermal stability. These materials can be used in various applications, including aerospace, automotive, construction, and other industries where advanced materials are required for specific performance characteristics.
Preparation
All involve iodination of trimethylsilylacetylenes.
Direct iodination of metalated (lithium or magnesium)
trimethylsilylacetylene has been largely supplanted
due to the modest yields obtained. Utilizing trimethylsilylacetylene
and bis(trimethylsilyl) peroxide in the presence
of copper(I) iodide gives good yields. Substituting zinc
iodide requires using the lithium acetylide. Copper(I) iodide
(0.05 equiv.) in the presence of iodine, sodium carbonate, and
a phase-transfer catalyst gives good yields without having to
use n-butyllithium or a Grignard reagent to first deprotonate
the trimethylsilylacetylene. The most popular procedure uses
bis(trimethylsilyl)acetylene, treating it with iodine monochloride
in dichloromethane at 25°Cto obtain excellent yields of
(iodoethynyl)trimethylsilane.
Check Digit Verification of cas no
The CAS Registry Mumber 18163-47-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,1,6 and 3 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 18163-47:
(7*1)+(6*8)+(5*1)+(4*6)+(3*3)+(2*4)+(1*7)=108
108 % 10 = 8
So 18163-47-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H9ISi/c1-7(2,3)5-4-6/h1-3H3
18163-47-8Relevant articles and documents
Copper(I)- and Phase Transfer-Catalysed Iodination of Terminal Alkynes
Jeffery, Tuyet
, p. 909 - 910 (1988)
A convenient synthesis of 1-iodoalk-1-ynes is reported, involving cooper(I)-catalysed iodination of terminal alkynes with molecular iodine under solid-liquid phase-transfer conditions.
SIRT1 Receptor agonists and drugs containing same
-
Paragraph 0110-0111; 0116; 0144-0145; 0147, (2021/10/13)
The present invention belongs to the field of medicaments or nutraceutical products, and specifically relates to a compound represented by the following general formula (I), or an enantiomer, diastereomer, salt, ester, prodrug, solvate, or solvate of a salt thereof, wherein R1, R2, and R3 are as defined in the specification of the present invention. The compound prepared by the present invention brings about an effect of activating Sirt1, and can be used as a potential Sirt1 agonist. By using a hyperuricemia animal model, the compound of the present invention is found to bring about an effect of significantly lowering the level of uric acid in the body, and can be used as a potential medicament for lowering the level of uric acid or treating gout.
Synthesis and reactions of a new 1,1-disubstituted cyclopentadiene
Camps, Pelayo,Gómez, Tània
scheme or table, p. 128 - 139 (2011/05/12)
The synthesis and several synthetic transformations of methyl 1-benzylcyclopenta-2,4-diene-1-carboxylate are described. ARKAT USA, Inc.
An alkynyliodide cycloaddition strategy for the construction of iodoisoxazoles
Crossley, James A.,Browne, Duncan L.
supporting information; scheme or table, p. 5414 - 5416 (2010/10/04)
(Figure presented) The thermally promoted cycloaddition between alkynyliodides and nitrile oxides is reported. The process offers excellent regioselectivity and a broad scope with respect to both the iodoalkynes and chloro-oximes. Further functionalization of the highly decorated iodoisoxazole motifs can be achieved via Suzuki cross-coupling.
