1-(1-Naphthyl)-2-(trimethylsilyl)acetylene

Base Information

• Chemical Name: 1-(1-Naphthyl)-2-(trimethylsilyl)acetylene
• CAS No.: 104784-51-2
• Molecular Formula: C15H16 Si
• Molecular Weight: 224.378
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID70403302
• Nikkaji Number: J1.797.285E
• Wikidata: Q82206934
• Mol file: 104784-51-2.mol

Synonyms:104784-51-2;1-(1-Naphthyl)-2-(trimethylsilyl)acetylene;trimethyl(2-naphthalen-1-ylethynyl)silane;TRIMETHYLNAPHTHALEN-1-YLETHYNYLSILANE;triMethyl(naphthalen-1-ylethynyl)silane;TRIMETHYL[2-(NAPHTHALEN-1-YL)ETHYNYL]SILANE;DTXSID70403302;WATBCTJRCLNXNF-UHFFFAOYSA-N;(1-Naphthylethynyl)trimethylsilane;1-(trimethylsilylethynyl)naphthalene;1-trimethylsilyl Ethynyl Naphthalene;MFCD04039886;Trimethyl[(1-naphthyl)ethynyl]silane;AKOS015913435;Trimethyl-naphthalen-1-ylethynyl-silane;AS-76291;CS-0440246;E83245;1-(1-Naphthyl)-2-(trimethylsilyl)acetylene, 97%;J-001254

Chemical Property of 1-(1-Naphthyl)-2-(trimethylsilyl)acetylene

Chemical Property:

• Vapor Pressure: 0.00168mmHg at 25°C
• Melting Point: 41-43℃
• Refractive Index: n20/D 1.595(lit.)
• Boiling Point: 292-293 °C(lit.)
• Flash Point: >230 °F
• PSA: 0.00000
• Density: 0.968 g/mL at 25 °C(lit.)
• LogP: 4.06870
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 224.102127045
• Heavy Atom Count: 16
• Complexity: 298

Purity/Quality:

98%min ^*data from raw suppliers

1-(1-Naphthyl)-2-(trimethylsilyl)acetylene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC=CC2=CC=CC=C21

Technology Process of 1-(1-Naphthyl)-2-(trimethylsilyl)acetylene

There total 25 articles about 1-(1-Naphthyl)-2-(trimethylsilyl)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: 100.0%

1-Iodonaphthalene (90-14-2) + trimethylsilylacetylene (1066-54-2) → 1-(trimethylsilyl)ethynylnaphthalene (104784-51-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol301474g

Reference yield: 97.0%

trimethylsilyl iodide (16029-98-4) + 1-ethynylnaphthalene (15727-65-8) → 1-(trimethylsilyl)ethynylnaphthalene (104784-51-2)

Guidance literature:

With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; In toluene; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.11.103

Reference yield: 94.0%

1-Bromonaphthalene (90-11-9) + trimethylsilylacetylene (1066-54-2) → 1-(trimethylsilyl)ethynylnaphthalene (104784-51-2)

Guidance literature:

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; at 80 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1246/cl.130584

upstream raw materials:

1-Bromonaphthalene

trimethylsilylacetylene

1-Iodonaphthalene

((trimethylsilyl)ethynyl)zinc(II) chloride

Downstream raw materials:

1-ethynylnaphthalene

Refernces

• 1、 Jiang, Bo,Jia, Jingwen,Sun, Yufei,Wang, Yichun,Zeng, Jing,Bu, Xiubin,Shi, Liangliang,Sun, Xiaoying,Yang, Xiaobo. "γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation". . p. 13389 - 13392. Retrieved 2020.
• 2、 Spain, Malcolm,Wong, Joseph K.-H.,Nagalingam, Gayathri,Batten, James M.,Hortle, Elinor,Oehlers, Stefan H.,Jiang, Xiao Fan,Murage, Hasini E.,Orford, Jack T.,Crisologo, Patrick,Triccas, James A.,Rutledge, Peter J.,Todd, Matthew H.. "Antitubercular Bis-Substituted Cyclam Derivatives: Structure-Activity Relationships and in Vivo Studies". . p. 3595 - 3608. Retrieved 2018.
• 3、 Ikeda, Akari,Omote, Masaaki,Kusumoto, Kana,Tarui, Atsushi,Sato, Kazuyuki,Ando, Akira. "One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon by an oxidative Sonogashira cross-coupling reaction". . p. 8886 - 8892. Retrieved 2015.
• 4、 Hau, Sam C.K.,Mak, Thomas C.W.. "Assembly of organosilver coordination frameworks with polycyclic benzenoid aromatic ethynide ligands". . p. 123 - 133. Retrieved 2015.
• 5、 Chang, Ning-Hui,Mori, Hiroki,Chen, Xi-Chao,Okuda, Yasuhiro,Okamoto, Takeru,Nishihara, Yasushi. "Synthesis of substituted [6]phenacenes through Suzuki-Miyaura coupling of polyhalobenzene with alkenylboronates and sequential intramolecular cyclization via C-H bond activation". . p. 1257 - 1259. Retrieved 2013.
• 6、 Yang, Dongdong,Shan, Lihong,Xu, Ze-Feng,Li, Chuan-Ying. "Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole". . p. 1461 - 1464. Retrieved 2018.
• 7、 Ibrahim, Jessica Juweriah,Yang, Yong,Zhang, Shaochun. "An NNN-Pincer-Cobalt Complex Catalyzed Highly Markovnikov-Selective Alkyne Hydrosilylation". . . Retrieved 2018.
• 8、 Biletskyi, Bohdan,Kong, Lingyu,Tenaglia, Alphonse,Clavier, Hervé. "Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines". . p. 2578 - 2585. Retrieved 2021.
• 9、 Lehnherr, Dan,Murray, Adrian H.,McDonald, Robert,Ferguson, Michael J.,Tykwinski, Rik R.. "Pentacene-based polycyclic aromatic hydrocarbon dyads with cofacial solid-state π-stacking". . p. 12580 - 12584. Retrieved 2009.
• 10、 Fukuyama, Takahide,Higashibeppu, Yuki,Yamaura, Ryo,Ryu, Ilhyong. "Ru-catalyzed intermolecular [3+2+1] cycloaddition of α,β- unsaturated ketones with silylacetylenes and carbon monoxide leading to α-pyrones". . p. 587 - 589. Retrieved 2007.