1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97

Base Information

• Chemical Name: 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97
• CAS No.: 18163-47-8
• Molecular Formula: C5H9ISi
• Molecular Weight: 224.116
• Hs Code.: 2931900090
• Mol file: 18163-47-8.mol

Synonyms:Silane,(iodoethynyl)trimethyl- (7CI,8CI,9CI);(Iodoethynyl)trimethylsilane;1-Iodo-2-(trimethylsilyl)acetylene;1-Iodo-2-(trimethylsilyl)ethyne;Iodo(trimethylsilyl)acetylene;

Chemical Property of 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97

Chemical Property:

• Vapor Pressure: 3.73mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 156.4 °C at 760 mmHg
• Flash Point: 48.4 °C
• PSA: 0.00000
• Density: 1.504 g/cm³
• LogP: 2.25970
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: sol organics (THF, Et2O, pyridine, DCM, CHCl3, DMF).

Purity/Quality:

99% ^*data from raw suppliers

1-Iodo-2-(trimethylsilyl)acetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/21/22-42/43-63
• Safety Statements: 16-23-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Physical properties: bp 96 °C, 55 °C/20 mmHg; n20 D 1.5110; d 1.46 g cm?3, fp 48°C.
• Uses: (Iodoethynyl)trimethylsilane is widely used as alkyne coupling reagent predominantly used in conjunction with organocopper species or palladium catalysis.(Iodoethynyl)trimethylsilane has been largely confined to aryl- and vinylcopper coupling, where it serves well since the reverse procedure, i.e. coupling with alkynylcopper reagents, is not straightforward due to the lack of reactivity of alkynyl moieties bound to copper. 1-Iodo-2-(trimethylsilyl)acetylene may be used to investigate the reactivity of diamagnetic cobalt(I) complex, Tol-BDI((2-pp)2)Co [Tol-BDI((2-pp)2)H = 2-(4-tolyl)-1,3-bis(2-isopropylpyridyl)propenediimine]. It may be used for the synthesis of 1-(4-trimethylsilanylbuta-1,3-diynyl)pyrene, via Pd-coupling with 1-iodo-2-trimethylsilylacetylene.

Technology Process of 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97

There total 4 articles about 1-IODO-2-(TRIMETHYLSILYL)ACETYLENE 97 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: 96.0%

trimethylsilylacetylene (1066-54-2) → iodoethynyltrimethylsilane (18163-47-8)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

With iodine;

DOI:10.3998/ark.5550190.0012.310

Reference yield: 90.0%

Bis(trimethylsilyl)ethyne (14630-40-1) → iodoethynyltrimethylsilane (18163-47-8)

Guidance literature:

With Iodine monochloride; In tetrachloromethane; Ambient temperature;

DOI:10.1016/0022-328X(89)87090-1

Reference yield:

chloro-trimethyl-silane (75-77-4) + acetylene (74-86-2,25067-58-7) → iodoethynyltrimethylsilane (18163-47-8)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/0040-4020(80)87021-9

upstream raw materials:

chloro-trimethyl-silane

acetylene

trimethylsilylacetylene

Bis(trimethylsilyl)ethyne

Downstream raw materials:

1-[tris(biphenyl-4-yl)silyl]-4-trimethylsilyl-1,3-butadiyne

Co[CH₃C₆H₄(C₃H₂(N(C(CH₃)2C₅H₄N))2)](CCSi(CH₃)3)I

trimethyl(4-phenylbuta-1,3-diyn-1-yl)silane

(Co3(μ-bis(diphenylphosphino)methane)(CO)7)2(μ3:μ3-C10)

Refernces

• 1、 Al-Hassan, Mohammed I.. "Halogenation of alkynes and alkynylsilanes". . p. 183 - 186. Retrieved 1989.
• 2、 Danilkina, Natalia A.,D'Yachenko, Alexander S.,Govdi, Anastasia I.,Khlebnikov, Alexander F.,Kornyakov, Ilya V.,Br?se, Stefan,Balova, Irina A.,Balova, Irina A.. "Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin". . p. 9001 - 9014. Retrieved 2020/08/14.
• 3、 Liu, Hui,Chen, Chen,Wang, Limin,Tong, Xiaofeng. "Pd(0)-catalyzed iodoalkynation of norbornene scaffolds: The remarkable solvent effect on reaction pathway". supporting information; experimental part. p. 5072 - 5075. Retrieved 2011/11/29.