2-(Trimethylsilyl)pyridine

Base Information

• Chemical Name: 2-(Trimethylsilyl)pyridine
• CAS No.: 13737-04-7
• Molecular Formula: C8H13NSi
• Molecular Weight: 151.283
• Hs Code.: 29333990
• European Community (EC) Number: 625-461-0
• NSC Number: 603436
• DSSTox Substance ID: DTXSID50160148
• Nikkaji Number: J151.401F
• Wikidata: Q72514563
• Mol file: 13737-04-7.mol

Synonyms:2-(Trimethylsilyl)pyridine;13737-04-7;Pyridine, 2-(trimethylsilyl)-;trimethyl(pyridin-2-yl)silane;2-pyridyltrimethylsilane;2-trimethylsilylpyridine;2-(Trimethylsilyl)pyridine, 98%;(2-pyridyl)trimethylsilane;NSC603436;trimethyl(2-pyridinyl)silane;Pyridine,2-(trimethylsilyl)-;SCHEMBL1299154;DTXSID50160148;IBLKFJNZUSUTPB-UHFFFAOYSA-N;MFCD06797181;AKOS005254816;NSC-603436;DS-14531;CS-0006221;FT-0645300;T2021;A807248;J-506689

Chemical Property of 2-(Trimethylsilyl)pyridine

Chemical Property:

• Appearance/Colour: Clear colorless to brown liquid
• Vapor Pressure: 1.16mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Boiling Point: 181.5 °C at 760 mmHg
• PKA: 6.62±0.10(Predicted)
• Flash Point: 63.6 °C
• PSA: 12.89000
• Density: 0.9 g/cm³
• LogP: 1.62680
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 151.081725953
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

2-(Trimethylsilyl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)C1=CC=CC=N1

Technology Process of 2-(Trimethylsilyl)pyridine

There total 5 articles about 2-(Trimethylsilyl)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: 80.0%

pyridine (110-86-1) + chloro-trimethyl-silane (75-77-4) → 2-(trimethylsilyl)pyridine (13737-04-7)

Guidance literature:

With n-butyllithium; 2-(N,N-dimethylamino)ethanol; 1.) hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h;

DOI:10.1039/a705027e

Reference yield: 65.0%

2-bromo-pyridine (109-04-6) + chloro-trimethyl-silane (75-77-4) → 2-(trimethylsilyl)pyridine (13737-04-7)

Guidance literature:

2-bromo-pyridine; With n-butyllithium;

chloro-trimethyl-silane; In diethyl ether; at -78 - 20 ℃;

DOI:10.1021/acs.inorgchem.7b00595

Reference yield:

2-chloropyridine (109-09-1) + chloro-trimethyl-silane (75-77-4) → 2-(trimethylsilyl)pyridine (13737-04-7)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; at 70 ℃; for 1h;

upstream raw materials:

pyridine

chloro-trimethyl-silane

2-chloropyridine

2-bromo-pyridine

Downstream raw materials:

2-(phenyltrimethylsiloxymethyl)-pyridine

phenyl(2-pyridinyl)methanol

pyridine

[(2-pyridyldimethylsilyl)methyl]benzene

Refernces

• 1、 Fischer et al.. "-". . p. 323,325-326, 330. Retrieved 1977.
• 2、 Nagaki, Aiichiro,Yamada, Daisuke,Yamada, Shigeyuki,Doi, Masatomo,Ichinari, Daisuke,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi. "Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems". . p. 199 - 207. Retrieved 2013/03/28.
• 3、 Gros, Philippe,Fort, Yves,Caubere, Paul. "Aggregative activation in heterocyclic chemistry. Part 5. Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE)". . p. 3597 - 3600. Retrieved 2007/10/03.