13361-64-3 Usage
Description
PROPARGYLTRIMETHYLSILANE, also known as 2-Propynyl-trimethylsilane or 3-Trimethylsilyl-1-propyne, is a clear colorless liquid that contains 500ppm of butylated hydroxytoluene (BHT) as a stabilizer. It is characterized by its unique chemical properties, including its ability to undergo various reactions such as propargylation, alkylation, and allenylation. It is also known for its physical properties, such as a boiling point of 91-93°C at 760 mmHg and a density of 0.753 g/mL.
Uses
Used in Chemical Synthesis:
PROPARGYLTRIMETHYLSILANE is used as a propargylation agent and an allenylation agent for its ability to give addition reactions on the triple bond. It is involved in a wide range of reactions, including propargylation reactions, alkylation reactions, reactions with epoxides, reactions with aldehydes and ketones, reactions with chloroformates, reactions with polyoxymethylene and amines, substitution reactions, reactions with acetals and hemiacetals, reactions with in situ generated iminium and α-acyl iminium ions, reactions with acid chlorides, and reactions with conjugated heteroatomic systems.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, PROPARGYLTRIMETHYLSILANE is used in the synthesis of diverse end-functionalized compounds, such as ω-carboxyl, ω-hydroxy, ω-methyl-vinyl, ω-trimethylsilane, and ω-glycidyl-ether, via "click" reactions. It may also be used in the synthesis of γ-allenyl-GABA (γ-aminobutyric acid) through a Lewis acid-mediated reaction with ω-ethoxy lactams.
Used in Material Science:
PROPARGYLTRIMETHYLSILANE can be utilized in the development of new materials with specific properties, such as those with tailored reactivity, stability, or functionality, due to its versatile reactivity and ability to participate in various chemical reactions.
Used in Research and Development:
As a versatile reagent, PROPARGYLTRIMETHYLSILANE is valuable in research and development for the exploration of new chemical reactions, the synthesis of novel compounds, and the investigation of reaction mechanisms. Its unique properties make it a useful tool for chemists working in various fields, including organic chemistry, materials science, and pharmaceutical chemistry.
Preparation
The main method of preparation is shown
in eq 1. The title reagent can be obtained by other methods, but in poor yields.
Purification Methods
Fractionally distil it and add 2,6-di-tert-butyl-p-cresol (~0.5%) to stabilise it. [Petrov et al. Doklady Acad Nauk USSR 93 293 1953, cf Chem Abstr 48 13616 1954, Beilstein 4 IV 3938.]
Check Digit Verification of cas no
The CAS Registry Mumber 13361-64-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,3,6 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13361-64:
(7*1)+(6*3)+(5*3)+(4*6)+(3*1)+(2*6)+(1*4)=83
83 % 10 = 3
So 13361-64-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H12Si/c1-5-6-7(2,3)4/h1H,6H2,2-4H3
13361-64-3Relevant articles and documents
ACTION DE SILANES PROPARGYLIQUES SUR DES DERIVES CARBONYLES α-ETHYLENIQUES
Pornet, Jaques,Kolani, N'Baneyape,Mesnard, Danielle,Miginiac, Leone,Jaworski, Krzysztof
, p. 177 - 188 (1982)
Propargylsilanes RCCCH2Si(CH3)3 easily react with dialkyl alkylidenemalonates, in the presence of TiCl4, to lead to the only product corresponding to an 1,4-addition; the reaction takes place with propargylic rearrangement.
Temporary silicon connection strategies in intramolecular allylation of aldehydes with allylsilanes
Beignet, Julien,Jervis, Peter J.,Cox, Liam R.
, p. 5462 - 5475 (2008/12/21)
(Chemical Equation Presented) Three γ-(amino)silyl-substituted allylsilanes 14a-c have been prepared in three steps from the corresponding dialkyldichlorosilane. The aminosilyl group has been used to link this allylsilane nucleophile to a series of β-hydroxy aldehydes through a silyl ether temporary connection. The size of the alkyl substituents at the silyl ether tether governs the outcome of the reaction on exposure to acid. Thus, treatment of aldehyde (E)-9aa, which contains a dimethylsilyl ether connection between the aldehyde and allylsilane, with a range of Lewis and Bronsted acid activators provides an (E)-diene product. The mechanism of formation of this undesired product is discussed. Systems containing a sterically more bulky diethylsilyl ether connection react differently: thus in the presence of TMSOTf and a Bronsted acid scavenger, intramolecular allylation proceeds smoothly to provide two out of the possible four diastereoisomeric oxasilacycles, 23 (major) and 21 (minor). A diene product again accounts for the remaining mass balance in the reaction. This side product can be completely suppressed by using a sterically even more bulky diisopropylsilyl ether connection in the cyclization precursor, although this is now at the expense of a slight erosion in the 1,3-stereoinduction in the allylation products. The sense of 1,3-stereoinduction observed in these intramolecular allylations has been rationalized by using an electrostatic argument, which can also explain the stereochemical outcome of a number of related reactions. Levels of 1,4-stereoinduction in the intramolecular allylation are more modest but can be significantly improved in some cases by using a tethered (Z)-allylsilane in place of its (E)-stereoisomer. Oxidation of the major diastereoisomeric allylation product 23 under Tamao-Kumada conditions provides an entry into stereodefined 1,2-anti-2,4-syn triols 28.
