2-(Tributylstannyl)pyridine

Product Number: T3254; CAS Number: 17997-47-6

T3254 Technical Data, Safety Info and Reactions 

SDS

$28.00$386.00

$28.00
$125.00
$386.00

2-(Tributylstannyl)pyridine 2-Pyridinetributylstannane CAS: 17997-47-6 MDL: MFCD00052052

SDS

Molecular weight: 368.1  g/mol

Molecular Formula: C17H31NSn

CAS Number: 17997-47-6

Storage: Store at 2-8 Co, under dry conditions.

Synonyms:  2-(Tributylstannyl)pyridine, 17997-47-6, 2-Tri-n-butylstannylpyridine, 2-TRIBUTYLSTANNYLPYRIDINE, Pyridine, 2-(tributylstannyl)-, tributyl(pyridin-2-yl)stannane, 2-Pyridyltributyltin, Tributyl(2-pyridyl)tin, 2-(1,1,1-tributylstannyl)pyridine, 2-tributylstannyl pyridine, 2-tributylstannyl-pyridine, MFCD00052052, tri-n-butyl(2-pyridyl)tin, 2-(tributylstannanyl)pyridine, 2-(tri-n-butylstannyl)pyridine, Pyridine,2-(tributylstannyl)-, tributylstannylpyridine, Tributyl-2-pyridyltin, tributylstannyl pyridine, (2-pyridyl)tributyltin, 2-pyridyl tributyl tin, PubChem15457, 2-pyridyltributyl stannane, 2-pyridyl tri-n-butyl tin, 2-tributylstannanyl pyridine, 2-tributylstannanyl-pyridine, tributyl(2-pyridyl)stannane, 2-pyridyltri-n-butylstannane, SCHEMBL28505

SAFETY GUIDELINES:  US Department of Health and Human Services Toxicological Profile for Tin and Tin Compounds

Uses: Stille Coupling Reactions, Transition Metal Reactions, Nitrogen heterocycle, synthetic building block, reactive tin, synthesis of specialty chemicals

2-(Tributylstannyl)pyridine, is a synthetic specialtychemical useful in the synthesis of pharmaceuticals.

Selected References:

1.) Allred, Gary D., and Lanny S. Liebeskind.   Copper-Mediated Cross-Coupling of Organostannanes with Organic Iodides at or below Room Temperature.   Journal of the American Chemical Society 118,  (1996): 2748–49. https://doi.org/10.1021/JA9541239.

2.) Dubbaka, Srinivas Reddy, and Pierre. Vogel.   Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes.   Journal of the American Chemical Society 125,  (2003): 15292–93. https://doi.org/10.1021/ja038328q.

3.) Echavarren, Antonio M., and J. K. Stille.   Palladium-Catalyzed Carbonylative Coupling of Aryl Triflates with Organostannanes.   Journal of the American Chemical Society 110,  (1988): 1557–65. https://doi.org/10.1021/ja00213a032.

4.) Palladium-Catalyzed Coupling of Aryl Triflates with Organostannanes.   Journal of the American Chemical Society 109,  (1987): 5478–86. https://doi.org/10.1021/ja00252a029.

5.) Egi, Masahiro, and Lanny S. Liebeskind.   Heteroaromatic Thioether-Organostannane Cross-Coupling.   Organic Letters 5,  (2003): 801–2. https://doi.org/10.1021/ol0273497.

6.) Espinet, Pablo, and Antonio M. Echavarren.   C-C Coupling: The Mechanisms of the Stille Reaction.   Angewandte Chemie, International Edition 43,  (2004): 4704–34. https://doi.org/10.1002/anie.200300638.

7.) Farina, Vittorio.   New Perspectives in the Cross-Coupling Reactions of Organostannanes.   Pure and Applied Chemistry 68,  (1996): 73–78. https://doi.org/10.1351/pac199668010073.

8.) Finet, Jean-Pierre, Alexey Yu. Fedorov, Sebastien Combes, and Gerard. Boyer.   Recent Advances in Ullmann Reaction: Copper(II) Diacetate Catalyzed N-, O- and S-Arylation Involving Polycoordinate Heteroatomic Derivatives.   Current Organic Chemistry 6,  (2002): 597–626. https://doi.org/10.2174/1385272023374058.

9.) Garcia-Martinez, Joaquin C., Raphael Lezutekong, and Richard M. Crooks.   Dendrimer-Encapsulated Pd Nanoparticles as Aqueous, Room-Temperature Catalysts for the Stille Reaction.   Journal of the American Chemical Society 127,  (2005): 5097–5103.https://doi.org/10.1021/ja042479r.

10.) Grasa, Gabriela A., and Steven P. Nolan.   Palladium/Imidazolium Salt Catalyzed Coupling of Aryl Halides with Hypervalent Organostannates.   Organic Letters 3,  (2001): 119–22. https://doi.org/10.1021/ol006827f.

11.) Hayashi, Tamio, and Mitsuo. Ishigedani.   Rhodium-Catalyzed Asymmetric Arylation of Imines with Organostannanes. Asymmetric Synthesis of Diarylmethylamines.   Journal of the American Chemical Society 122,  (2000): 976–77. https://doi.org/10.1021/ja9927220.

12.) Kang, Suk-Ku, Tokutaro Yamaguchi, Tae-Hyun Kim, and Pil-Su. Ho.   Copper-Catalyzed Cross-Coupling and Carbonylative Cross-Coupling of Organostannanes and Organoboranes with Hypervalent Iodine Compounds.   Journal of Organic Chemistry 61,  (1996): 9082–83. https://doi.org/10.1021/JO962033W.

13.) Labadie, Jeff W., and J. K. Stille.   Mechanisms of the Palladium-Catalyzed Couplings of Acid Chlorides with Organotin Reagents.   Journal of the American Chemical Society 105,  (1983): 6129–37. https://doi.org/10.1021/ja00357a026.

14.) Liu, Songbai, Ying Yu, and Lanny S. Liebeskind.   N-Substituted Imines by the Copper-Catalyzed N-Imination of Boronic Acids and Organostannanes with O-Acyl Ketoximes.   Organic Letters 9,  (2007): 1947–50. https://doi.org/10.1021/ol070561w.

15.) Navarre, Laure, Remi Martinez, Jean-Pierre Genet, and Sylvain. Darses.   Access to Enantioenriched α-Amino Esters via Rhodium-Catalyzed 1,4-Addition/Enantioselective Protonation.   Journal of the American Chemical Society 130,  (2008): 6159–69. https://doi.org/10.1021/ja710691p.

16.) Scott, William J., and John E. McMurry.   Olefin Synthesis via Organometallic Coupling Reactions of Enol Triflates.   Accounts of Chemical Research 21,  (1988): 47–54. https://doi.org/10.1021/ar00146a001.

17.) Scott, William J., and J. K. Stille.   Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes.  Synthetic and Mechanistic Studies.   Journal of the American Chemical Society 108,  (1986): 3033–40. https://doi.org/10.1021/ja00271a037.

18.) Shen, Wang, and Le. Wang.   The Stille Reaction of 1,1-Dibromo-1-Alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes.   Journal of Organic Chemistry 64,  (1999): 8873–79. https://doi.org/10.1021/jo991116k.

19.) Urkalan, Kaveri Balan, and Matthew S. Sigman.   Palladium-Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen.   Angewandte Chemie, International Edition 48,  (2009): 3146–49, S3146/1-S3146/64. https://doi.org/10.1002/anie.200900218.

20.) Wittenberg, Ruediger, Jiri Srogl, Masahiro Egi, and Lanny S. Liebeskind.   Ketone Synthesis under Neutral Conditions. Cu(I) Diphenylphosphinate-Mediated, Palladium-Catalyzed Coupling of Thiol Esters and Organostannanes.   Organic Letters 5,  (2003): 3033–35. https://doi.org/10.1021/ol034962x.

Categories

Purity %

85-95%

Molecular Formula

C17H31NSn

Molecular Weight

368.13

CAS #

17997-47-6

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