Cyclopropyl(trimethylsilyl)acetylene

Base Information

• Chemical Name: Cyclopropyl(trimethylsilyl)acetylene
• CAS No.: 81166-84-9
• Molecular Formula: C8H14Si
• Molecular Weight: 138.285
• Hs Code.: 29310099
• DSSTox Substance ID: DTXSID80374130
• Nikkaji Number: J2.904.850I
• Wikidata: Q72460822
• Mol file: 81166-84-9.mol

Synonyms:81166-84-9;CYCLOPROPYL(TRIMETHYLSILYL)ACETYLENE;(Cyclopropylethynyl)trimethylsilane;2-cyclopropylethynyl(trimethyl)silane;(2-cyclopropylethynyl)trimethylsilane;Silane, (cyclopropylethynyl)trimethyl-;(cyclopropylethynyl)(trimethyl)silane;C8H14Si;cyclopropylethynyl-trimethylsilane;DTXSID80374130;trimethylsilylcyclopropyl-acetylene;cyclopropylethynyl-trimethyl-silane;IYQSVLJDYLPMCX-UHFFFAOYSA-N;Trimethyl(cyclopropylethynyl)silane;AMY42221;BCP30704;CS-M3250;MFCD00671355;AKOS006339862;AS-43738;A9979;FT-0641810;S05385;2-METHYL-5-(1,2,3,4-TETRAHYDROXYBUTYL)-3-FUROICACID;[2-(Trimethylsilyl)ethynyl]cyclopropane pound>>(2-cyclopropylethynyl)trimethylsilane

Chemical Property of Cyclopropyl(trimethylsilyl)acetylene

Chemical Property:

• Appearance/Colour: Clear colorless to yellow liquid
• Vapor Pressure: 12.2mmHg at 25°C
• Refractive Index: 1.4547
• Boiling Point: 129.8 °C at 760 mmHg
• Flash Point: 24.6 °C
• PSA: 0.00000
• Density: 0.85 g/cm³
• LogP: 2.27720
• Storage Temp.: Flammables area
• Solubility.: Sparingly Soluble (0.069 g/L) (25°C).
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 138.086476981
• Heavy Atom Count: 9
• Complexity: 158

Purity/Quality:

98%min ^*data from raw suppliers

Cyclopropyl(trimethylsilyl)acetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1CC1
• Uses: Cyclopropyl(trimethylsilyl)acetylene is used in several addition reactions.

Technology Process of Cyclopropyl(trimethylsilyl)acetylene

There total 7 articles about Cyclopropyl(trimethylsilyl)acetylene 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: 81.0%

(5-chloropent-1-ynyl)trimethylsilane (77113-48-5) → (2-cyclopropylethynyl)trimethylsilane (81166-84-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; -78 deg C to r.t.;

DOI:10.1055/s-1993-25988

Reference yield: 80.0%

chloro-trimethyl-silane (75-77-4) + Cyclopropylacetylene (6746-94-7) → (2-cyclopropylethynyl)trimethylsilane (81166-84-9)

Guidance literature:

Cyclopropylacetylene; With methyllithium; In diethyl ether; at -78 - -60 ℃; Inert atmosphere;

chloro-trimethyl-silane; In diethyl ether; at -78 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0030-1258964

Reference yield: 62.0%

chloro-trimethyl-silane (75-77-4) + 1-chloro-1-(trichloroethenyl)cyclopropane (82979-27-9) → (2-cyclopropylethynyl)trimethylsilane (81166-84-9) + 1-(Trimethylsilyl)-1-<(trimethylsilyl)ethinyl>cyclopropan (83662-48-0)

Guidance literature:

With magnesium; In tetrahydrofuran; for 18h; Heating;

upstream raw materials:

chloro-trimethyl-silane

Cyclopropylacetylene

1-chloro-1-(trichloroethenyl)cyclopropane

(5-chloropent-1-ynyl)trimethylsilane

Downstream raw materials:

dimethyl cis-but-2-ene-1,4-dioate

1-trimethylsilyl-2-cyclopropylcyclopropene-3-carboxylic acid methyl ester

dimethylfumarate

Cyclopropylacetylene

Refernces

• 1、 Ciszewski, Lukasz W.,Durka, Jakub,Gryko, Dorota. "Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters". supporting information. p. 7028 - 7032. Retrieved 2019/09/12.
• 2、 Liu, Wen-Bo,Schuman, David P.,Yang, Yun-Fang,Toutov, Anton A.,Liang, Yong,Klare, Hendrik F. T.,Nesnas, Nasri,Oestreich, Martin,Blackmond, Donna G.,Virgil, Scott C.,Banerjee, Shibdas,Zare, Richard N.,Grubbs, Robert H.,Houk,Stoltz, Brian M.. "Potassium tert-Butoxide-Catalyzed Dehydrogenative C-H Silylation of Heteroaromatics: A Combined Experimental and Computational Mechanistic Study". supporting information. p. 6867 - 6879. Retrieved 2017/05/31.