1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE

Base Information

• Chemical Name: 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE
• CAS No.: 4526-07-2
• Molecular Formula: C10H18 Si2
• Molecular Weight: 194.424
• Hs Code.: 29319090
• Mol file: 4526-07-2.mol

Synonyms:2,7-Disilaocta-3,5-diyne,2,2,7,7-tetramethyl- (6CI,7CI,8CI); Silane, 1,3-butadiyne-1,4-diylbis[trimethyl-(9CI); 1,3-Butadiyne-1,4-diylbis[trimethylsilane];1,3-Butadiynylenebis[trimethylsilane]; 1,4-Bis(trimethylsilyl)-1,3-butadiyne;1,4-Bis(trimethylsilyl)butadiyne; Bis(trimethylsilyl)-1,3-butadiyne;Bis(trimethylsilyl)butadiyne; Bis(trimethylsilyl)diacetylene;Trimethyl(4-(trimethylsilyl)-1,3-butadiynyl)silane

Chemical Property of 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE

Chemical Property:

• Appearance/Colour: light yellow to light beige cryst.powder or flakes
• Vapor Pressure: 0.525mmHg at 25°C
• Melting Point: 111-113 °C(lit.)
• Refractive Index: n20/D 1.384(lit.)
• Boiling Point: 197.7°C at 760 mmHg
• Flash Point: >45°C
• PSA: 0.00000
• Density: 0.974 g/mL at 20 °C(lit.)
• LogP: 2.74800
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble in water.

Purity/Quality:

98% ^*data from raw suppliers

1,4-Bis(trimethylsilyl)-1,3-butadiyne ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,4-Bis(trimethylsilyl)-1,3-butadiyne is used in Negishi protocol for the synthesis of glycosylated oligo(ethynylene)s. It is also used as pharmaceutical intermediates. 1,4-Bis(trimethylsilyl)butadiyne can be used as a reagent to prepare:1,1,3,4-Tetrasilyl-substituted 1,3-butadienes or 1,1,3,4-tetrasilyl-substituted 1,2-butadienes by hydrosilylation reaction using various hydridosilanes and catalysts.Glycosylated oligo(ethynylene)s using the Negishi reaction.(±) Falcarinol, a polyacetylene class of fatty alcohol.

Technology Process of 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE

There total 37 articles about 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE 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: 99.0%

4-bromo-benzaldehyde (1122-91-4) + trimethylsilylacetylene (1066-54-2) → 1,4-bis(trimethylsilyl)-1,3-butadiyne (4526-07-2) + 4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 25 ℃; Yields of byproduct given;

DOI:10.1021/jo9808021

Reference yield: 95.0%

1-bromo-2,5-dioctyl-4-iodobenzene (848290-34-6) + trimethylsilylacetylene (1066-54-2) → 1-(4-bromo-2,5-dioctylphenyl)-2-(trimethylsilyl)acetylene (848290-36-8) + 1,4-bis[(trimethylsilyl)ethynyl]-2,5-dioctylbenzene + 1,4-bis(trimethylsilyl)-1,3-butadiyne (4526-07-2)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; Title compound not separated from byproducts; cooling;

DOI:10.1021/ma048489u

Reference yield: 92.0%

para-bromoacetophenone (99-90-1) + trimethylsilylacetylene (1066-54-2) → 1,4-bis(trimethylsilyl)-1,3-butadiyne (4526-07-2) + 4'-(2-trimethylsilylethynyl)acetophenone (75883-03-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 25 ℃; Yields of byproduct given;

DOI:10.1021/jo9808021

upstream raw materials:

1-pentynyl copper

(2-bromoethynyl)trimethylsilane

trimethyl(trimethylstannanylethynyl)silane

1,3-dibromobenzene

Downstream raw materials:

(3,5,6-tris((trimethylsilyl)ethynyl)benzene-1,2,4-triyl)tris(trimethylsilane)

1,3,5-tris((trimethylsilyl)ethynyl)-2,4,6-tris(trimethylsilyl)benzene

5-(Trimethylsilylmethyl)isoxazol

1-((trimethylsilyl)buta-1,3-diyn-1-yl)cyclohexanol

Refernces

• 1、 Plater, M. John,Aiken, Stuart,Bourhill, Grant. "Cooperative assembly of a double-stranded hydrogen-bonded porphyrin zip". . p. 2225 - 2229. Retrieved 2001.
• 2、 Su, Lebin,Dong, Jianyu,Liu, Long,Sun, Mengli,Qiu, Renhua,Zhou, Yongbo,Yin, Shuang-Feng. "Copper Catalysis for Selective Heterocoupling of Terminal Alkynes". supporting information. p. 12348 - 12351. Retrieved 2016/10/07.