(TRIETHYLSILYL)ACETYLENE

Base Information

• Chemical Name: (TRIETHYLSILYL)ACETYLENE
• CAS No.: 1777-03-3
• Molecular Formula: C8H16Si
• Molecular Weight: 140.301
• Hs Code.: 29319090
• Mol file: 1777-03-3.mol

Synonyms:(Triethylsilyl)acetylene;(Triethylsilyl)ethyne;Triethylethynylsilane;

Chemical Property of (TRIETHYLSILYL)ACETYLENE

Chemical Property:

• Appearance/Colour: Clear colorless to faintly yellow liquid
• Vapor Pressure: 7.75mmHg at 25°C
• Melting Point: 95-97 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 140.2 °C at 760 mmHg
• Flash Point: 17.2 °C
• PSA: 0.00000
• Density: 0.779 g/cm³
• LogP: 2.66730
• Storage Temp.: Flammables area

Purity/Quality:

99% ^*data from raw suppliers

(Triethylsilyl)acetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (Triethylsilyl)acetylene may be used in the synthesis of triethylsilylethynyl anthradithiophenes, such as : 2,8-dimethyl-5,11-bis(triethylsilylethynyl)ADT (ADT= anthradithiophene)2,8-diethyl-5,11-bis(triethylsilylethynyl)ADT2,8-dipropyl-5,11-bis(triethylsilylethynyl)ADT

Technology Process of (TRIETHYLSILYL)ACETYLENE

There total 10 articles about (TRIETHYLSILYL)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: 83.0%

triethylsilyl chloride (994-30-9) + acetylene (74-86-2,25067-58-7) → 2-triethylsilylacetylene (1777-03-3)

Guidance literature:

acetylene; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 1h;

triethylsilyl chloride; In tetrahydrofuran; Further stages.;

DOI:10.1021/jo025745x

Reference yield: 82.0%

triethylsilyl chloride (994-30-9) + sodium acetylide (1066-26-8) → 2-triethylsilylacetylene (1777-03-3)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 12h; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;

Reference yield:

triethylsilyl chloride (994-30-9) + Trichloroethylene (79-01-6) → 2-triethylsilylacetylene (1777-03-3)

Guidance literature:

With lithium; In tetrahydrofuran;

DOI:10.1016/S0022-328X(00)80233-8

upstream raw materials:

triethyl-bromo-silane

acetylenemagnesium bromide

triethylsilyl chloride

Trichloroethylene

Downstream raw materials:

1,2,4,5-Tetrafluoro-3,6-bis-triethylsilanylethynyl-benzene

1-Triaethylsilyl-6-mesityl-hexa-1,3,5-triin

1-Triaethylsilyl-8-mesityl-octa-1,3,5,7-tetrain

1-Triaethylsilyl-10-mesityl-deca-1,3,5,7,9-pentain

Refernces

An unexpected S_N′ reaction on cobaltocenium triflates: Substitution on one ring and elimination on the other

10.1021/om030182g

The study aims to demonstrate a novel reaction pathway where nucleophiles attack one ring of a cobaltocenium ion while the leaving group is at the other ring, leading to a substitution on one cyclopentadienone ring and elimination on the other. The researchers used various chemicals in their experiments, including organolithium compounds like MeLi, n-BuLi, and PhLi, as well as (trimethylsilyl)acetylene and (triethylsilyl)acetylene to introduce alkyne units into the Cp ring. The conclusions drawn from the research highlight the dramatic change in charge distribution due to the presence of a triflate group, which can be rationalized by electron density transfer from the Cp fragment to the cyclopentadienyloxy fragment, and the practical application of this process in synthesis, particularly in the formation of RCpCo-capped tetra-n-propyl-cyclopentadienone complexes with high yields.