Trimethylsilylacetylene
Names | |
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Preferred IUPAC name
Ethynyltri(methyl)silane | |
Identifiers | |
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3D model (JSmol)
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Abbreviations | TMSA |
ChemSpider | |
ECHA InfoCard | 100.012.655 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C5H10Si | |
Molar mass | 98.220 g·mol−1 |
Appearance | colorless liquid |
Density | 0.69 g/mL |
Boiling point | 53 °C (127 °F; 326 K) |
Hazards | |
Safety data sheet (SDS) | External MSDS |
GHS labelling: | |
Signal word
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Danger |
H225, H315, H318, H319, H335 | |
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
what is ?) | (|
Infobox references | |
Trimethylsilylacetylene is a colorless liquid that is a derivative of acetylene. Called "tms acetylene", it is used as a source of "HC2−". The trimethylsilyl group can then be cleaved off with TBAF. Using this protected alkyne, as opposed to acetylene itself, prevents further coupling reactions and also has the benefit of being a liquid.[1] A less expensive alternative reagent is 2-methylbut-3-yn-2-ol, which after alkynylation is deprotected with base.
Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride.[2]
Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne.[3]
References[]
- ^ Godson C. Nwokogu, Saskia Zemolka, Florian Dehme (2007). "Trimethylsilylacetylene". EROS. doi:10.1002/047084289X.rt288.pub2. ISBN 978-0471936237.CS1 maint: uses authors parameter (link)
- ^ Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses.; Collective Volume, 8, p. 606
- ^ Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1987). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Organic Syntheses. 65: 52. doi:10.15227/orgsyn.065.0052.CS1 maint: multiple names: authors list (link)
- Alkyne derivatives
- Carbosilanes
- Trimethylsilyl compounds