1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE

Base Information

• Chemical Name: 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE
• CAS No.: 2170-06-1
• Molecular Formula: C11H14Si
• Molecular Weight: 174.318
• Hs Code.: 29319090
• Mol file: 2170-06-1.mol

Synonyms:1-Phenyl-2-(trimethylsilyl)acetylene;1-Phenyl-2-(trimethylsilyl)ethyne;2-Phenyl-1-(trimethylsilyl)acetylene;2-Phenyl-1-ethynyltrimethylsilane;Phenyl(trimethylsilyl)acetylene;Phenyl(trimethylsilyl)ethyne;Trimethyl(phenylethynyl)silane;Silane,trimethyl(phenylethynyl)- (6CI,7CI,8CI,9CI);(Phenylacetylenyl)trimethylsilane;(Phenylethynyl)trimethylsilane;(Trimethylsilyl)phenylacetylene;(Trimethylsilylethynyl)benzene;1-(Trimethylsilyl)-2-phenylacetylene;1-(Trimethylsilyl)-2-phenylethyne;

Chemical Property of 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE

Chemical Property:

• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Boiling Point: 217.4 °C at 760 mmHg
• Flash Point: 73.9 °C
• PSA: 0.00000
• Density: 0.91g/cm³
• LogP: 2.91550
• Storage Temp.: 2-8°C
• Solubility.: Sparingly Soluble (6.1E-3 g/L) (25°C)

Purity/Quality:

99.0% ^*data from raw suppliers

1-Phenyl-2-(trimethylsilyl)acetylene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 1-Phenyl-2-trimethylsilylacetylene was used in the preparation of donor-stabilized Pt-η2-alkyne complexes.

Technology Process of 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE

There total 133 articles about 1-PHENYL-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%

bromobenzene (108-86-1,52753-63-6) + trimethylsilylacetylene (1066-54-2) → 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1)

Guidance literature:

With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1002/adsc.200606135

Reference yield: 90.0%

trimethylsilyl iodide (16029-98-4) + phenylacetylene (536-74-3) → 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1)

Guidance literature:

With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; In toluene; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1021/om200038r

Reference yield: 85.0%

iodobenzene (591-50-4) + (trimethylsilylethynyl)tributyltin (81353-38-0) → 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1)

Guidance literature:

iodobenzene; With diphenylphosphinoethane functionalized polystyrene resin-supported Pd⁽⁰⁾ complex; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

(trimethylsilylethynyl)tributyltin; In N,N-dimethyl-formamide; at 65 ℃; for 9h;

DOI:10.1139/v2012-044

upstream raw materials:

n-butyllithium

phenylacetylene

ethylmagnesium bromide

chloro-trimethyl-silane

Downstream raw materials:

1-chloro-4-phenyl-3-butyn-2-one

1,4-Dichlor-2-trimethylsilyl-1-phenyl-buten-⁽¹⁾-on-⁽³⁾

phenylacetylene

1-Trimethylsiloxy-1-(phenylethynyl)cyclohexane

Refernces

• 1、 Novokshonov,Medvedeva,Mareev. "Effect of the Grignard reagent on the X→Csp, migration of the MR3 group in HC ≡ CCH2XMR3 compounds". . p. 1549 - 1552. Retrieved 2001.
• 2、 Hommes, Hendrik,Verkruijsse, Hermann D.,Brandsma, Lambert. "Dimetallation of Phenylacetylene. Selective ortho-Substitution". . p. 366 - 367. Retrieved 1981.
• 3、 Sun, Fenggang,Gu, Zhenhua. "Decarboxylative Alkynyl Termination of Palladium-Catalyzed Catellani Reaction: A Facile Synthesis of α-Alkynyl Anilines via Ortho C - H Amination and Alkynylation". . p. 2222 - 2225. Retrieved 2015.
• 4、 Kunai, Atsutaka,Mihara, Toshiyuki,Matsuo, Yoichi,Ohshita, Joji,Naka, Akinobu,Ishikawa, Mitsuo. "Thermolysis of 1,1-dimesityl-3-phenyl-2-trimethylsilyl-1-silacyclopropene: Silylene transfer reactions to 1,4-bis(silyl)butadiynes". . p. 611 - 613. Retrieved 1997.
• 5、 Wang, Miao,So, Chau Ming. "Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes". supporting information. p. 681 - 685. Retrieved 2022/01/20.
• 6、 Sun, Xu,Guo, Xiao-Qiang,Chen, Lian-Mei,Kang, Tai-Ran. "Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes". supporting information. p. 4312 - 4316. Retrieved 2021/02/06.