3-(Trimethylsilylethynyl)pyridine

Base Information

• Chemical Name: 3-(Trimethylsilylethynyl)pyridine
• CAS No.: 80673-00-3
• Molecular Formula: C10H13 N Si
• Molecular Weight: 175.305
• Hs Code.: 29333990
• European Community (EC) Number: 627-532-1
• DSSTox Substance ID: DTXSID30399318
• Nikkaji Number: J1.543.340J
• Wikidata: Q72514473
• Mol file: 80673-00-3.mol

Synonyms:80673-00-3;3-((Trimethylsilyl)ethynyl)pyridine;3-(Trimethylsilylethynyl)pyridine;3-[(Trimethylsilyl)ethynyl]pyridine;trimethyl(2-pyridin-3-ylethynyl)silane;3-[2-(trimethylsilyl)ethynyl]pyridine;(3-Pyridylethynyl)trimethylsilane;3-trimethylsilylethynylpyridine;SCHEMBL2922495;3-(Trimethysilylethynyl)pyridine;DTXSID30399318;MTMBLPOPETZZRX-UHFFFAOYSA-N;MFCD01863744;AKOS015908763;CS-W017436;1-(3-Pyridyl)-2-trimethylsilylacetylene;AS-62138;trimethyl-[2-(3-pyridinyl)ethynyl]silane;3-[(Trimethylsilyl)ethynyl]pyridine, 97%;FT-0656304;T1963;T72959;A839962;InChI=1/C10H13NSi/c1-12(2,3)8-6-10-5-4-7-11-9-10/h4-5,7,9H,1-3H

Chemical Property of 3-(Trimethylsilylethynyl)pyridine

Chemical Property:

• Appearance/Colour: transparent liquid
• Vapor Pressure: 0.19mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Boiling Point: 218 °C
• Flash Point: 94 °C
• PSA: 12.89000
• Density: 0.922 g/cm³
• LogP: 2.31050
• Storage Temp.: Freezer
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 175.081725953
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-((Trimethylsilyl)ethynyl)pyridine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CN=CC=C1

Technology Process of 3-(Trimethylsilylethynyl)pyridine

There total 12 articles about 3-(Trimethylsilylethynyl)pyridine 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: 93.0%

3-Bromopyridine (626-55-1,163928-56-1) + trimethylsilylacetylene (1066-54-2) → 3-[(trimethylsilyl)ethynyl]pyridine (80673-00-3)

Guidance literature:

With copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; diisopropylamine; at 30 ℃; for 3h;

DOI:10.1081/SCC-120021834

Reference yield: 90.0%

5-bromopyridine-3-carbaldehyde (113118-81-3) + trimethylsilylacetylene (1066-54-2) → 3-[(trimethylsilyl)ethynyl]pyridine (80673-00-3)

Guidance literature:

With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; at 20 ℃; Inert atmosphere;

Reference yield: 87.0%

3-Bromopyridine (626-55-1,163928-56-1) + Na(1+)*((CH3)3SiCC)4Al(1-) → 3-[(trimethylsilyl)ethynyl]pyridine (80673-00-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; for 12h; Heating;

DOI:10.1021/jo020169q

upstream raw materials:

3-Bromopyridine

trimethylsilylacetylene

3-bromopyridine hydrochloride

pyridine-3-carbonitrile

Downstream raw materials:

3-(1-benzyl-1H-[1,2,3]triazol-4-yl)-pyridine

C₂₅H₂₆F₃N₇O

(4-(acetylthio)phenyl)(3-pyridyl)acetylene

dimethyl 6'-((4-(acetylthio)phenyl)ethynyl)-8a'H-spiro[fluorene-9,1'-indolizine]-2',3'-dicarboxylate

Refernces

• 1、 Bennett, Troy L. R.,Wilkinson, Luke A.,Lok, Jasmine M. A.,O'Toole, Robert C. P.,Long, Nicholas J.. "Synthesis, Electrochemistry, and Optical Properties of Highly Conjugated Alkynyl-Ferrocenes and -Biferrocenes". . p. 1156 - 1162. Retrieved 2021/05/06.
• 2、 Xie, Zhicheng,Wu, Bing,Liu, Yingqiang,Ren, Wenming,Tong, Linjiang,Xiang, Caigui,Wei, Aihuan,Gao, Yuanzhuo,Zeng, Limin,Xie, Hua,Tang, Wei,Hu, Youhong. "Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on an o-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders". . p. 1397 - 1414. Retrieved 2020/02/04.