4526-07-2

Basic information

• Product Name: 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE
• Synonyms: 1,4-Bis(trimethylsilyl)-1,3-butanediyne;1,4-Bis(trimethylsilyl)-1-butyne-3-yne;1,4-Bis(trimethylsilyl)butane-1,3-diyne;1,4-Di(trimethylsilyl)-1,3-butadiyne;Bis(trimethylsilyl)-1,3-butadiyne;4-Bis(trimethylsilyl)-1,3-butadiyne;1,4-Bis(trimethylsilyl)buta-1,3-diyne;1,4-Bis(trimethylsilyl)butadiyne 98%, stable crystalline form of butadiyne
• CAS NO: 4526-07-2
• Molecular Formula: C₁₀H₁₈Si₂
• Molecular Weight: 194.42
• EINECS: -0
• Product Categories: Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Alkynes;Building Blocks;Chemical Synthesis;Internal;Organic Building Blocks;Diyne Compounds (LB Films);LB Films;Acetylenes;Ethynylsilanes;Functional Materials;Functionalized Acetylenes;Si (Classes of Silicon Compounds)
• Mol File: 4526-07-2.mol

Chemical Properties

• Melting Point: 111-113 °C(lit.)
• Boiling Point: 197.7°C at 760 mmHg
• Flash Point: >45°C
• Appearance: /solid
• Density: 0.974 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.525mmHg at 25°C
• Refractive Index: n20/D 1.384(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water.
• BRN: 1758268
• CAS DataBase Reference: 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE(4526-07-2)
• EPA Substance Registry System: 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE(4526-07-2)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-22-24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 4526-07-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE is used as a pharmaceutical intermediate for the synthesis of various bioactive compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE is used as a reagent in the Negishi protocol for the synthesis of glycosylated oligo(ethynylene)s. This reaction allows for the formation of complex molecular structures with potential applications in materials science and medicinal chemistry.
Additionally, 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE can be used to prepare 1,1,3,4-tetrasilyl-substituted 1,3-butadienes or 1,1,3,4-tetrasilyl-substituted 1,2-butadienes through hydrosilylation reactions using various hydridosilanes and catalysts. This provides a versatile route to access a range of functionalized butadiyne derivatives for further applications in organic synthesis.
Furthermore, 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE is used in the synthesis of (±) Falcarinol, a polyacetylene class of fatty alcohol with potential biological activities. 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE has been studied for its potential applications in various fields, including medicine and agriculture.

InChI:InChI=1/C10H18Si2/c1-11(2,3)9-7-8-10-12(4,5)6/h1-6H3

Upstream product

• 19093-51-7 1-pentynyl copper 
• 18243-59-9 (2-bromoethynyl)trimethylsilane 
• 16035-50-0 trimethyl(trimethylstannanylethynyl)silane 
• 108-36-1 1,3-dibromobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 73513-58-3 1,2-dichloro-4,5-diiodobenzene 
• 99-90-1 para-bromoacetophenone 
• 536-74-3 phenylacetylene 
• 693-02-7 hex-1-yne 
• 1122-91-4 4-bromo-benzaldehyde 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 618-89-3 methyl 3-bromobenzoate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 54655-07-1 lithium trimethylsilylacetylenide 

Downstream Products

• 37176-71-9 2-(5-Trimethylsilanyl-penta-2,4-diynoyl)-benzoic acid 
• 18765-46-3 (3,5,6-tris((trimethylsilyl)ethynyl)benzene-1,2,4-triyl)tris(trimethylsilane) 
• 18823-04-6 1,3,5-tris((trimethylsilyl)ethynyl)-2,4,6-tris(trimethylsilyl)benzene 
• 71482-87-6 5-(Trimethylsilylmethyl)isoxazol 
• 73084-24-9 1-((trimethylsilyl)buta-1,3-diyn-1-yl)cyclohexanol 
• 37166-49-7 p-Tolyl-trimethylsilyl-butadiin-keton 
• 37166-51-1 p-Methoxyphenyl-trimethylsilyl-butadiin-keton 
• 37166-50-0 p-Nitrophenyl-trimethylsilyl-butadiin-keton 
• 83182-77-8 3-Phenyl-5-(trimethylsilyl)-4-<(trimethylsilyl)ethinyl>pyridazin 
• 147196-69-8 4-(2-Tetrahydropyranyloxy)-1-(4-(trimethylsilyl)-1,3-butadiynyl)cyclohexanol 
• 130741-05-8 2,2,6-Trimethyl-1-(4-trimethylsilanyl-buta-1,3-diynyl)-cyclohexanol 
• 103716-81-0 (E)-2-dimethylphenylsilyl-1,4-bis(trimethylsilyl)-1-buten-3-yne 
• 103716-82-1 1,3-bis(dimethylphenylsilyl)-1,4-bis(trimethylsilyl)-1,2-butadiene 
• 103737-69-5 (E)-2-methylphenylsilyl-1,4-bis(trimethylsilyl)-1-buten-3-yne 

Relevant articles and documents

Interaction of the buchwald seven-membered zirconacyclocumulene complex with carbonyl compounds

The interaction of the Buchwald seven-membered zirconacyclocumulene Cp2Zr[4-Me3SiC4(SiMe3)-C(C2SiMe3)=CSiMe3] (1) with a 2-fold excess of benzophenone in toluene at 100 °C for 20 h results in the formation of Me3SiCC-CCSiMe3 and a nine-membered dioxazirconacycle Cp2Zr[2-OC(Ph)2C(SiMe3)C2C(SiMe3)C(Ph)2O] (5) containing [3]cumulene group in the ring. Analogous metallacycle (6) is formed on heating of 1 with fluorenone in toluene at 100 °C. A treatment of 5 with HCl in dioxane at 20 °C affords Cp2ZrCl2 and cis-[3]cumulenic diol Ph2(HO)C(Me3Si)CC2C(SiMe3)C(OH)Ph2 (7) in 85% yield. The reaction of 1 with benzil (PhCO)2 at 80 °C in benzene proceeds differently than with benzophenone and fluorenone. In this case, a nine-membered dioxazirconacycle Cp2Zr[2-Me3SiCaC(C2SiMe3)-C(SiMe3) C(C2SiMe3)OC(Ph) C(Ph)O] (10) is produced. The nature of products formed in the interaction of 1 with acenaphthenequinone proved to be temperature dependent. Thus, on carrying out the reaction at 20 °C, an 11-membered trioxazirconacycle (11) containing three CaC bonds in the ring was isolated from the mixture, whereas at 80 °C the reaction gave a ten-membered tetraoxadizirconacycle (12) and octasubstituted cyclooctatetraene [(Me3Si)CaC(CCSiMe3)]4 (13). The structures of 5-7 and 10-13 have been determined by X-ray diffraction. The mechanism of the reactions found is discussed.

Cooperative assembly of a double-stranded hydrogen-bonded porphyrin zip

A linear zinc porphyrin dimer has been used for the first time to stabilise two identical non-covalent aggregates by a combination of N-pyridyl zinc binding and hydrogen bonding. An improved multigram synthesis of 5,15-bis-(3,5-di-tert-butylphenyl)-10,20-

Tuning of cross-Glaser products mediated by substrate-catalyst polymeric backbone interactions

Tuning of cross-Glaser products using different polymeric backbones supported by copper oxide nano-catalysts has been demonstrated by tweaking the substrate-catalyst interactions under greener conditions. Further, highly reactive magnetically separable and recyclable catalyst with scalability is demonstrated.

Copper Catalysis for Selective Heterocoupling of Terminal Alkynes

A Cu-catalyzed selective aerobic heterocoupling of terminal alkynes is disclosed, which enables the synthesis of a broad range of unsymmetrical 1,3-diynes in good to excellent yields. The results disprove the long-held belief that homocouplings are exclusively favored in the Glaser-Hay reaction.

Cyclization of gold acetylides: Synthesis of vinyl sulfonates via gold vinylidene complexes

Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example. Gold vinylidene intermediates are generated by the cyclization of gold acetylides that carry a sulfonate leaving group. This result demonstrates for the first time that the formation of these species is not restricted to a dual activation mode. The cyclization products obtained herein contain a vinyl sulfonate moiety, which makes them useful building blocks for cross-coupling reactions.

Halogen bonding of (iodoethynyl)benzene derivatives in solution

Halogen bonding (XB) between (iodoethynyl)benzene donors and quinuclidine in benzene affords binding free enthalpies (δG, 298 K) between -1.1 and -2.4 kcal mol-1, with a strong LFER with the Hammett parameter σpara. The enthalpic dri

Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition

[3+2]-cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5-disubstituted-4-(trimethyl-silyl)-1H-1,2,3-triazoles. The formation of the 1,5-isomer is highly favored in this metal-free cycloaddition, which could be proven by 1D selective NOESY and X-ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5-isomer. The described method provides a simple alternative protocol to metal-catalyzed "click chemistry" procedures, widening the scope for regioselective heavy-metal-free synthetic applications.

Fluoro-substituted phenyleneethynylenes: Acetylenic n-type organic semiconductors

Fluoro-substituted phenyleneethynylenes are synthesized by Sonogashira coupling and acetylide-nucleophilic substitution of fluorobenzenes. Fluoro-substitution of benzenes enables deep LUMO potential, and CF 3-substitution provides high electron

The sequential Sonogashira-click reaction: A versatile route to 4-aryl-1,2,3-triazoles

Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.

4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors

A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.