(TRIISOPROPYLSILYL)ACETYLENE

Base Information

• Chemical Name: (TRIISOPROPYLSILYL)ACETYLENE
• CAS No.: 89343-06-6
• Molecular Formula: C11H22Si
• Molecular Weight: 182.381
• Hs Code.: 29319090
• European Community (EC) Number: 629-580-9
• DSSTox Substance ID: DTXSID30370445
• Nikkaji Number: J890.896F
• Wikidata: Q72513658
• Mol file: 89343-06-6.mol

Synonyms:Ethynyltriisopropylsilane;Ethynyltris(1-methylethyl)silane;Ethynyltris(triisopropyl)silane;Triisopropylacetylene;Triisopropylsilylacetylene;Triisopropylsilylethyne;

Chemical Property of (TRIISOPROPYLSILYL)ACETYLENE

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.0981mmHg at 25°C
• Melting Point: 50-51 °C
• Refractive Index: n20/D 1.4527(lit.)
• Boiling Point: 230.746 °C at 760 mmHg
• Flash Point: 56.111 °C
• PSA: 0.00000
• Density: 0.79 g/cm³
• LogP: 3.83760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Miscible with organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 182.149077236
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

Triisopropylsilylacetylene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si](C#C)(C(C)C)C(C)C
• Physical properties: colorless clear liquid; bp 50–52 °C at 0.8 hPa (0.6 mmHg), flash point 56 °C (closed cup); d = 0.813.
• Uses: (Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes. (Triisopropylsilyl)acetylene (TIPS-acetylene) is an easily handled and inexpensive monoprotected acetylene used as an attractive substitute for trimethylsilylacetylene (TMSacetylene). The bulkier silyl protecting group of TIPS-acetylene provides stability in a wider range of reaction conditions than TMS-acetylene. Its higher boiling point also provides better handling and safety than TMS-acetylene (bp 87–88°C at 12 hPa (9 mmHg)). The general utility of TIPS-acetylene is often highlighted in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc.

Technology Process of (TRIISOPROPYLSILYL)ACETYLENE

There total 7 articles about (TRIISOPROPYLSILYL)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: 85.0%

4-{Dimethyl-[(triisopropylsilanyl)-ethynyl]-silanyl}-biphenyl (136449-68-8) → tris-iso-propylsilyl acetylene (89343-06-6)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/S0040-4039(00)79376-2

Reference yield: 34.0%

tris(1-methylethyl)(phenylethynyl)silane (4131-50-4) → (Z,Z)-2,3-diphenyl-1,4-bis(triisopropylsilyl)-1,3-butadiene + trans-5,10-dihydro-5,10-bis(triisopropylsilyl)dibenzo[a,e]pentalene + cis-5,10-dihydro-5,10-bis(triisopropylsilyl)dibenzo[a,e]pentalene + tris-iso-propylsilyl acetylene (89343-06-6)

Guidance literature:

tris(1-methylethyl)(phenylethynyl)silane; With lithium; In diethyl ether; at 20 ℃; for 6h;

With water; In diethyl ether;

DOI:10.3987/COM-08-11547

Reference yield:

triiso-propyl(3-(4-methoxybenzyloxy)prop-1-ynyl)silane → tris-iso-propylsilyl acetylene (89343-06-6)

Guidance literature:

triiso-propyl(3-(4-methoxybenzyloxy)prop-1-ynyl)silane; With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 20 ℃; for 3.25h; Inert atmosphere;

With manganese(IV) oxide; potassium hydroxide; In diethyl ether; for 7h;

DOI:10.1002/anie.200905419

upstream raw materials:

4-{Dimethyl-[(triisopropylsilanyl)-ethynyl]-silanyl}-biphenyl

ethyl bromide

triisopropylsilyl chloride

acetylene

Downstream raw materials:

(E)-1-(6-methyl-1-cyclohexenyl)-3-triisopropylsilyl-2-propen-1-ol

1-t-butyl-3-[(triisopropylsilyl)ethynyl]-5-[(trimethylsilyl)ethynyl]benzene

ethyl 3-[(trimethylsilyl)ethynyl]-5-[(triisopropylsilyl)ethynyl]benzoate

1,3-bis(4-((triisopropylsilyl)ethynyl)phenyl)propan-2-one

Refernces

• 1、 Gonzalez, Davinia Fernandez,Brand, Jonathan P.,Waser, Jerome. "Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters". supporting information; experimental part. p. 9457 - 9461. Retrieved 2010/10/03.
• 2、 Saito, Masaichi,Nakamura, Michio,Tajima, Tomoyuki. "Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole". experimental part. p. 657 - 668. Retrieved 2009/06/08.