(tert-Butyldimethylsilyl)acetylene

Base Information

• Chemical Name: (tert-Butyldimethylsilyl)acetylene
• CAS No.: 86318-61-8
• Molecular Formula: C8H16 Si
• Molecular Weight: 140.301
• Hs Code.: 29319090
• European Community (EC) Number: 626-735-2
• Nikkaji Number: J316.654F
• Mol file: 86318-61-8.mol

Synonyms:86318-61-8;(tert-Butyldimethylsilyl)acetylene;TERT-BUTYLDIMETHYLSILYLACETYLENE;ethynyl-t-butyldimethylsilane;TERT-BUTYL(ETHYNYL)DIMETHYLSILANE;tert-butyl-ethynyl-dimethylsilane;tert-butyl-ethynyl-dimethyl-silane;Silane, (1,1-dimethylethyl)ethynyldimethyl-;(tert-Butyldimethylsilyl)ethyne;t-butyldimethylsilylacetylene;tert-Butyldimethylsilylethyne;tert-butylethynyldimethylsilane;(tert-Butyl)ethynyldimethylsilane;RTYNRTUKJVYEIE-UHFFFAOYSA-N;tert-butyl(ethynyl)-dimethylsilane;(tert-butyldimethyl-silyl)acetylene;MFCD00191877;AKOS006223448;(tert-Butyldimethylsilyl)acetylene, 99%;B4365;FT-0695320;P20672

Chemical Property of (tert-Butyldimethylsilyl)acetylene

Chemical Property:

• Vapor Pressure: 12mmHg at 25°C
• Melting Point: 98-102℃ (chloroform hexane )
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 116-117 °C(lit.)
• Flash Point: 43 °F
• PSA: 0.00000
• Density: 0.751 g/mL at 25 °C(lit.)
• LogP: 2.66730
• Storage Temp.: Flammables area
• Water Solubility.: Sparingly soluble in water (0.043 g/L at 25°C).
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 140.102127045
• Heavy Atom Count: 9
• Complexity: 140

Purity/Quality:

97% ^*data from raw suppliers

Tert-Butyldimethylsilylacetylene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-23-24/25-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)C#C
• Uses: tert-Butyldimethylsilylacetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.

Technology Process of (tert-Butyldimethylsilyl)acetylene

There total 2 articles about (tert-Butyldimethylsilyl)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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + acetylene (74-86-2,25067-58-7) → (tert-butyldimethylsilyl)acetylene (86318-61-8)

Guidance literature:

acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; hexane; at 20 ℃; for 24h; Further stages.;

DOI:10.1002/ejoc.200700201

Reference yield: 41.0%

tert-butyldimethylsilyl chloride (18162-48-6) + acetylenemagnesium bromide (4301-14-8) → (tert-butyldimethylsilyl)acetylene (86318-61-8)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 8h; Heating;

Reference yield: 96.0%

(tert-butyldimethylsilyl)acetylene (86318-61-8) + benzoyl chloride (98-88-4) → 1-oxo-1-phenyl-3-(tert-butyldimethylsilyl)prop-2-yne

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.666667h;

DOI:10.1039/b414826f

upstream raw materials:

tert-butyldimethylsilyl chloride

acetylenemagnesium bromide

acetylene

Downstream raw materials:

2-<2-<(1,1-dimethylethyl)dimethylsilyl>ethynyl>-3,4,5-trimethoxybenzenemethanol TMS ether

(S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

C₄₇H₆₁N₃Si₂

(3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol