Trimethylsilylacetylene

Base Information

• Chemical Name: Trimethylsilylacetylene
• CAS No.: 1066-54-2
• Deprecated CAS: 1042949-84-7,1277091-35-6,959419-58-0,1277091-35-6,959419-58-0
• Molecular Formula: C5H10Si
• Molecular Weight: 98.2199
• Hs Code.: 29310095
• European Community (EC) Number: 213-919-9,685-813-4
• DSSTox Substance ID: DTXSID7061435
• Nikkaji Number: J209.060K
• Wikipedia: Trimethylsilylacetylene
• Wikidata: Q3044982
• Mol file: 1066-54-2.mol

Synonyms:Trimethylsilylacetylene;Ethynyltrimethylsilane;1066-54-2;(Trimethylsilyl)acetylene;ethynyl(trimethyl)silane;ethynyl-trimethyl-silane;Silane, ethynyltrimethyl-;trimethylsilyl acetylene;TMS acetylene;TMS-acetylene;trimethylsilylethyne;(Trimethylsilyl)ethyne;C5H10Si;(Trimethylsilyl)acetylene-d;EINECS 213-919-9;ethynyltrimethyl silane;trimethylsilyl-acetylene;tms-acetylide;TMSacetylene;(tms)-acetylene;trimethylsilyl-ethyne;ethinyltrimethylsilane;ethynyitrimethylsilane;trimethylsilanylethyne;trimethylsilylacetylen;MFCD00008569;Trimethylethynylsilane;Trimetylsilylacetylene;TMSA;trimethlysilylacetylene;ethinyl trimethylsilane;ethynyl trimethylsilane;trimethysilyl acetylene;trimetylsilyl acetylene;1-Trimethylsilylethyne;Ethyne,-trimethylsilyl;Ethynyl-trimethylsilane;trimethyl silylacetylene;trimethyl-silylacetylene;trimethylsilyl acetylide;1-trimethylsilyl-ethyne;trimethylsilanylacetylene;(ethynyl)trimethylsilane;(trimethylsily)acetylene;(trimethylsilyl)acetylen;ethynyl-trimethyl silane;Ethynyl trimethyl silane;1-trimethylsilylacetylene;2-trimethylsilylacetylene;trimethyl silyl acetylene;trimethylsilanyl acetylene;(trimethyl-silyl)acetylene;(trimethylsilyl)-acetylene;(trimethylsilanyl)acetylene;(Trimethylsilyl) acetylene;Acetylene, trimethylsilyl-;1-ethynyl(trimethyl)silane;1-(Trimethylsilyl)acetylene;Ethynyltrimethylsilane, 98%;Silane, trimethyl-, ethynyl-;C5-H10-Si;DTXSID7061435;(Trimethylsilyl)Acetylene, 98%;AMY1236;BCP14441;STR06547;AKOS000121121;BP-30047;(TRIMETHYLSILYL)ACETYLENE, 98+%,;CS-0015355;T1239;EN300-27134;A801480;J-802298;Q-101308;Q3044982;F0001-0134

Chemical Property of Trimethylsilylacetylene

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 4.18 psi ( 20 °C)
• Melting Point: >0 °C
• Refractive Index: n20/D 1.388(lit.)
• Boiling Point: 53 °C at 760 mmHg
• Flash Point: <?30°F
• PSA: 0.00000
• Density: 0.752 g/cm³
• LogP: 1.49700
• Storage Temp.: 2-8°C
• Solubility.: Miscible with organic solvents.
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 98.055176853
• Heavy Atom Count: 6
• Complexity: 77.8

Purity/Quality:

99% ^*data from raw suppliers

Ethynyltrimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)C#C
• Physical properties: bp 53 °C; d 0.695 g cm?3.
• Uses: (Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone. Ethynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes Trimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.

Technology Process of Trimethylsilylacetylene

There total 46 articles about Trimethylsilylacetylene 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: 100.0%

4-bromo-3,3-dimethyl-1-(trimethylsilyl)-1-butyne → isobutene (115-11-7,15220-85-6) + trimethylsilylacetylene (1066-54-2)

Guidance literature:

With diisobutylaluminium hydride; In pentane; at 25 ℃; for 0.5h;

DOI:10.1021/ja00224a025

Reference yield: 94.0%

1-bromo-1-(trimethylsilyl)ethene (13683-41-5) → trimethylsilylacetylene (1066-54-2)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 40 - 110 ℃; for 2h; Solvent;

Reference yield: 91.4%

chloro-trimethyl-silane (75-77-4) + lithium acetylide (70277-75-7) → trimethylsilylacetylene (1066-54-2)

Guidance literature:

chloro-trimethyl-silane; lithium acetylide; 4,4'-di-tert-butylbiphenyl; In tetrahydrofuran; at 0 ℃; for 2h;

With water; In tetrahydrofuran; at 20 ℃;

upstream raw materials:

chloro-trimethyl-silane

sodium acetylide

chloroethynyl-trimethyl-silane

trimethylsilyl iodide

Downstream raw materials:

trans-1-(Chlordimethylsilyl)-2-(trimethylsilyl)ethen

3-methyl-5-trimethylsilyl-isoxazole

[Chloro-methyl-((E)-2-trimethylsilanyl-vinyl)-silanyl]-benzene

chloroethynyl-trimethyl-silane

Refernces

• 1、 Barton, Thomas J.,Groh, Brian L.. "Thermal Extrusion of Dimethylsilanone from (Hydridosilyl)ketenes. A Retro-Wolff Rearrangement?". . p. 7221 - 7222. Retrieved 1985.
• 2、 Morisaki, Kazuhiro,Sawa, Masanao,Yonesaki, Ryohei,Morimoto, Hiroyuki,Mashima, Kazushi,Ohshima, Takashi. "Mechanistic Studies and Expansion of the Substrate Scope of Direct Enantioselective Alkynylation of α-Ketiminoesters Catalyzed by Adaptable (Phebox)Rhodium(III) Complexes". . p. 6194 - 6203. Retrieved 2016.
• 3、 Yan, Kaking,Duchimaza Heredia, Juan J.,Ellern, Arkady,Gordon, Mark S.,Sadow, Aaron D.. "Lewis base mediated β-elimination and lewis acid mediated insertion reactions of disilazido zirconium compounds". . p. 15225 - 15237. Retrieved 2013.
• 4、 Krueerke,U.. "-". . p. 83 - 90. Retrieved 1970.
• 5、 Plater, M.John,Aiken, Stuart,Bourhill, Grant. "A new synthetic route to donor-acceptor porphyrins". . p. 2405 - 2413. Retrieved 2002.
• 6、 Brandsma,Verkruijsse. "Simple procedures for ethynylmagnesium bromide, ethynyltrialkylsilanes and ethynyltrialkylstannanes". . p. 1727 - 1728. Retrieved 1999.
• 7、 Cook et al.. "". . p. 301,302, 305. Retrieved 1970.
• 8、 Warren, Timothy H.,Bakhoda, Abolghasem,Okoromoba, Otome E.,Greene, Christine,Boroujeni, Mahdi Raghibi,Bertke, Jeffery A.. "Three-coordinate copper(II) alkynyl complex in C-C bond formation: The sesquicentennial of the glaser coupling". supporting information. p. 18483 - 18490. Retrieved 2020/11/27.