Trimethyl(2-pyridyl)tin

Base Information

• Chemical Name: Trimethyl(2-pyridyl)tin
• CAS No.: 13737-05-8
• Molecular Formula: C8H13NSn
• Molecular Weight: 241.908
• Hs Code.: 29333990
• European Community (EC) Number: 691-530-7
• DSSTox Substance ID: DTXSID80452225
• Wikidata: Q82272713
• Mol file: 13737-05-8.mol

Synonyms:Trimethyl(2-pyridyl)tin;13737-05-8;Pyridine, 2-(trimethylstannyl)-;2-Trimethylstannylpyridine;2-(trimethylstannyl)pyridine;trimethyl(pyridin-2-yl)stannane;2-pyridyltrimethyltin;Trimethyl-2-pyridyltin;Trimethyl-2 -pyridyltin;2-trimethylstannyl pyridine;2-trimethylstannyl-pyridine;2-trimethylstannanylpyridine;2-trimethylstannanyl pyridine;2-Trimethylstannanyl-pyridine;SCHEMBL482333;trimethyl(2-pyridinyl)stannane;DTXSID80452225;HDWHGDDNMJOCCU-UHFFFAOYSA-N;MFCD01631312;AKOS015840045;T1742;T71744;A807249

Chemical Property of Trimethyl(2-pyridyl)tin

Chemical Property:

• Refractive Index: 1.5380 to 1.5400
• Boiling Point: 223.4 °C at 760 mmHg
• PKA: 7.56±0.10(Predicted)
• Flash Point: 88.9 °C
• PSA: 12.89000
• Density: 1.4 g/cm³
• LogP: 1.62680
• Storage Temp.: Refrigerator
• 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:

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

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

Safty Information:

• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Sn](C)(C)C1=CC=CC=N1
• Uses: 2-(Trimethylstannyl)pyridine is a useful synthetic intermediate. It is used to prepare L-mannonic acid derivatives as HIV-1 protease inhibitors. It is also used to synthesize aryl indole NK1 receptor antagonists.

Technology Process of Trimethyl(2-pyridyl)tin

There total 16 articles about Trimethyl(2-pyridyl)tin 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: 88.0%

2-bromo-pyridine (109-04-6) + trimethyltin(IV)chloride (1066-45-1) → 2-trimethylstannylpyridine (13737-05-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; under N2, n-BuLi in hexane cooled to -78°C, dild. with Et2O, ethereal soln. of heterocycle added dropwise with stirring, stirred for a while, after addn. of soln. of Me3SnCl in THF allowed to warm to room temp.; concd. in vac., methylcyclohexane added, filtered, fractionally distd.;elem. anal.;

DOI:10.1016/0022-328X(83)80196-X

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: 84.0%

diethyl 2-chloropyridin-3-yl phosphate (53682-85-2) + trimethyltin(IV)chloride (1066-45-1) + sodium (7440-23-5) → 2,3-bis(trimethylstannyl)pyridine (83674-65-1) + 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 20 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., distd in vac., NMR and MS;

DOI:10.1016/j.jorganchem.2010.08.032

upstream raw materials:

2-bromo-pyridine

trimethyltin(IV)chloride

sodium

trimethylpyridin-2-ylammonium iodide

Downstream raw materials:

2,2'-(5-bromo-1,3-phenylene)dipyridine

[2,2]bipyridinyl

4-pyridin-2-yl-benzoic acid methyl ester

1-(4-Fluoro-phenyl)-2-imidazol-1-yl-1-(4-pyridin-2-yl-phenyl)-ethanol

Refernces

• 1、 Riedmiller, Frank,Jockisch, Alexander,Schmidbaur, Hubert. "Synthesis and molecular structures of 2-trimethylsilyl-, 2-trimethylgermyl-, and 2-trimethylstannyl-pyridines". . p. 13 - 17. Retrieved 1999.
• 2、 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.
• 3、 Rudenko, Andrey E.,Clayman, Naomi E.,Walker, Katherine L.,Maclaren, Jana K.,Zimmerman, Paul M.,Waymouth, Robert M.. "Ligand-Induced Reductive Elimination of Ethane from Azopyridine Palladium Dimethyl Complexes". supporting information. p. 11408 - 11415. Retrieved 2018/09/12.