3-(Trimethylstannyl)pyridine

Base Information

• Chemical Name: 3-(Trimethylstannyl)pyridine
• CAS No.: 59020-09-6
• Molecular Formula: C8H13NSn
• Molecular Weight: 241.908
• DSSTox Substance ID: DTXSID80446508
• Mol file: 59020-09-6.mol

Synonyms:59020-09-6;3-(trimethylstannyl)pyridine;Trimethyl(3-pyridyl)tin;3-trimethylstannylpyridine;Pyridine,3-(trimethylstannyl)-;trimethyl-3-pyridyltin;3-pyridyltrimethylstannane;3-trimethylstannyl pyridine;3-Trimethylstannanyl-pyridine;SCHEMBL361574;DTXSID80446508;Pyridine, 3-(trimethylstannyl)-;VDHNKGVVXBUCFR-UHFFFAOYSA-N;LS-132123

Chemical Property of 3-(Trimethylstannyl)pyridine

Chemical Property:

• Boiling Point: 223.4 °C at 760 mmHg
• PKA: 5.28±0.10(Predicted)
• Flash Point: 88.9 °C
• PSA: 12.89000
• LogP: 1.62680
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 243.007002
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

TRIMETHYL(3-PYRIDYL)TIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Sn](C)(C)C1=CN=CC=C1

Technology Process of 3-(Trimethylstannyl)pyridine

There total 17 articles about 3-(Trimethylstannyl)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: 89.0%

(E)-3-((methylsulfonyl)diazenyl)pyridine + hexamethyldistannane (661-69-8) → 3-(trimethylstannyl)pyridine (59020-09-6)

Guidance literature:

In acetonitrile; at 20 ℃; Irradiation; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01788

Reference yield: 87.0%

diethyl 5-chloropyridin-2-yl phosphate (1256814-27-3) + trimethyltin(IV)chloride (1066-45-1) + sodium (7440-23-5) → 2,5-bis(trimethylstannyl)pyridine (83674-67-3) + 3-(trimethylstannyl)pyridine (59020-09-6) + 2-trimethylstannylpyridine (13737-05-8)

Guidance literature:

In ammonia; NH3 (liquid); Irradiation (UV/VIS); (inert atm.); addn. of 4.4 equiv. of sodium to soln. of 2.2 equiv. of tin compd. in liquid ammonia, addn. of 1 equiv. of pyridine deriv., stirring with irradiation for 30 min; quenching with methyl iodide, adn. of diethyl ether, evapn. of ammonia, treating with water, extn. (diethyl ether), washing with water and brine, drying over MgSO4, filtration, evapn., recrystn. (ethanol), NMR and MS;

DOI:10.1016/j.jorganchem.2010.08.032

Reference yield: 86.0%

3-iodopyridine (1120-90-7) + hexamethyldistannane (661-69-8) → 3-(trimethylstannyl)pyridine (59020-09-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 1h; UV-irradiation; Sealed tube; Inert atmosphere;

DOI:10.1039/c6cc01135g

upstream raw materials:

3-Bromopyridine

hexamethyldistannane

trimethyltin(IV)chloride

diethyl pyridin-3-yl phosphate

Downstream raw materials:

2,3'-bipyridine

3-(3'-bromophenyl)pyridine

3-(4-bromophenyl)pyridine

methyl 4-nitro-2-(3-pyridyl)benzoate

Refernces

• 1、 Mao, Shuai,Chen, Zhengkai,Wang, Lu,Khadka, Daulat Bikram,Xin, Minhang,Li, Pengfei,Zhang, San-Qi. "Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature". . p. 463 - 471. Retrieved 2019/01/10.
• 2、 Chen, Kai,He, Pei,Zhang, Shuai,Li, Pengfei. "Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method". supporting information. p. 9125 - 9128. Retrieved 2016/07/21.