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
• Article Data: 22

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

Chemical Properties

light yellow to light beige cryst.powder or flakes

Uses

Different sources of media describe the Uses of 4526-07-2 differently. You can refer to the following data:
1. 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.
2. 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.

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 
• 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 
• 17356-09-1 4-iodocumene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 119-61-9 benzophenone 
• 1622092-91-4 (2-bromo-4-fluorophenoxy)(tert-butyl)dimethylsilane 

Downstream Products

• 37166-49-7 p-Tolyl-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 
• 20932-80-3 1,1,1,4,4,4-hexakis(trimethylsilyl)butin-2 
• 16954-96-4 diacetylene-d2 
• 177852-56-1 [4-(4-Methoxymethoxy-3,5-dimethyl-phenyl)-buta-1,3-diynyl]-trimethyl-silane 
• 103716-83-2 (E)-2-diphenylsilyl-1,4-bis(trimethylsilyl)-1-buten-3-yne 
• 51440-56-3 1-Methoxy-4-(1-methoxy-vinyl)-benzene 
• 136053-40-2 4-Methoxy-2-trimethylsilanyl-1-trimethylsilanylethynyl-benzene 
• 214409-47-9 5-Trimethylsilanyl-1-{2-[4-(2-trimethylsilanylethynyl-phenyl)-buta-1,3-diynyl]-phenyl}-penta-2,4-diyn-1-ol 
• 214409-49-1 1-(2-{4-[2-(4-Phenyl-buta-1,3-diynyl)-phenyl]-buta-1,3-diynyl}-phenyl)-5-trimethylsilanyl-penta-2,4-diyn-1-ol 
• 214409-48-0 1-{2-[4-(2-Phenylethynyl-phenyl)-buta-1,3-diynyl]-phenyl}-5-trimethylsilanyl-penta-2,4-diyn-1-ol 
• 16900-51-9 1,4-bis(2-thienyl)butadiyne 

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.

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.

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