126225-57-8

Basic information

• Product Name: TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE
• Synonyms: 6-METHYL-2-(TRIMETHYLSTANNYL)PYRIDINE;TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE
• CAS NO: 126225-57-8
• Molecular Formula: C₉H₁₅NSn
• Molecular Weight: 255.934
• Mol File: 126225-57-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE(126225-57-8)
• EPA Substance Registry System: TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE(126225-57-8)

Safety Data

• Hazardous Substances Data: 126225-57-8(Hazardous Substances Data)

Usage

General Description

TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE is a chemical compound that consists of a tin atom bonded to three methyl groups and a 6-methyl-2-pyridyl group. It is commonly used as a reagent in organic synthesis, particularly in cross-coupling reactions to form carbon-carbon bonds. TRIMETHYL-(6-METHYL-2-PYRIDYL)STANNANE is sensitive to air and moisture, requiring careful handling and storage conditions. It is known for its ability to facilitate the selective synthesis of various organic molecules and is widely used in the pharmaceutical and agrochemical industries for the production of advanced intermediates and complex molecules.

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 1066-45-1 trimethyltin(IV)chloride 

Downstream Products

• 130897-00-6 6-bromo-6′-methyl-2,2′-bipyridine 
• 33777-92-3 6,6-dimethyl-2,2':6',2-terpyridine 
• 263012-82-4 1-[5-(6'-methyl-2,2'-bipyridyl)]-4-[5-(2-bromopyridyl)]benzene 
• 879410-67-0 4,6-bis(6-methylpyridin-2-yl)-2-phenylpyrimidine 
• 195603-40-8 3-(6'-Methyl-[2,2']bipyridinyl-6-yl)-prop-2-yn-1-ol 

Relevant articles and documents

Largazole Analogues Embodying Radical Changes in the Depsipeptide Ring: Development of a More Selective and Highly Potent Analogue

A number of analogues of the marine-derived histone deacetylase inhibitor largazole incorporating major structural changes in the depsipeptide ring were synthesized. Replacing the thiazole-thiazoline fragment of largazole with a bipyridine group gave analogue 7 with potent cell growth inhibitory activity and an activity profile similar to that of largazole, suggesting that conformational change accompanying switching hybridization from sp3 to sp2 at C-7 is well tolerated. Analogue 7 was more class I selective compared to largazole, with at least 464-fold selectivity for class I HDAC proteins over class II HDAC6 compared to a 22-fold selectivity observed with largazole. To our knowledge 7 represents the first example of a potent and highly cytotoxic largazole analogue not containing a thiazoline ring. The elimination of a chiral center derived from the unnatural amino acid R-a-methylcysteine makes the molecule more amenable to chemical synthesis, and coupled with its increased class I selectivity, 7 could serve as a new lead compound for developing selective largazole analogues.

Synthesis and Isomeric Analysis of RuII Complexes Bearing Pentadentate Scaffolds

A RuII-pentadentate polypyridyl complex [RuII(κ-N5-bpy2PYMe)Cl]+ (1+, bpy2PYMe = 1-(2-pyridyl)-1,1-bis(6-2,2′-bipyridyl)ethane) and its aqua derivative [RuII(κ-N5-bpy2PYMe)(H2O)]2+ (22+) were synthesized and characterized by experimental and computational methods. In MeOH, 1+ exists as two isomers in different proportions, cis (70%) and trans (30%), which are interconverted under thermal and photochemical conditions by a sequence of processes: chlorido decoordination, decoordination/recoordination of a pyridyl group, and chlorido recoordination. Under oxidative conditions in dichloromethane, trans-12+ generates a [RuIII(κ-N4-bpy2PYMe)Cl2]+ intermediate after the exchange of a pyridyl ligand by a Cl- counterion, which explains the trans/cis isomerization observed when the system is taken back to Ru(II). On the contrary, cis-12+ is in direct equilibrium with trans-12+, with absence of the κ-N4-bis-chlorido RuIII-intermediate. All these equilibria were modeled by density functional theory calculations. Interestingly, the aqua derivative is obtained as a pure trans-[RuII(κ-N5-bpy2PYMe)(H2O)]2+ isomer (trans-22+), while the addition of a methyl substituent to a single bpy of the pentadentate ligand leads to the formation of a single cis isomer for both chlorido and aqua derivatives [RuII(κ-N5-bpy(bpyMe)PYMe)Cl]+ (3+) and [RuII(κ-N5-bpy(bpyMe)PYMe)(H2O)]2+ (42+) due to the steric constraints imposed by the modified ligand. This system was also structurally and electrochemically compared to the previously reported [RuII(PY5Me2)X]n+ system (X = Cl, n = 1 (5+); X = H2O, n = 2 (62+)), which also contains a κ-N5-RuII coordination environment, and to the newly synthesized [RuII(PY4Im)X]n+ complexes (X = Cl, n = 1 (7+); X = H2O, n = 2 (82+)), which possess an electron-rich Hκ-N4C-RuII site due to the replacement of a pyridyl group by an imidazolic carbene.

Electronic influence of the thienyl sulfur atom on the oligomerization of ethylene by cobalt(II) 6-(thienyl)-2-(imino)pyridine catalysis

The position of the sulfur atom in the thienyl group of 6-(thienyl)-2-(imino)pyridine ligands strongly affects the catalytic activity of the corresponding tetrahedral high-spin dihalide CoII complexes in the oligomerization of ethylene to α-olefins upon activation with methylaluminoxane (MAO). Complexes with the sulfur atom in the 3-position of the thienyl ring catalyze the selective conversion of ethylene to 1-butene, while catalysts containing thien-2-yl groups give C4-C14 a-olefins. In situ EPR experiments showed the occurrence of a spin state changeover with the formation of low-spin CoII species upon activation of the catalyst precursors by MAO. DFT calculations suggest that only thien-2-yl rings allow for the coordination of the sulfur atom to the cobalt center in the MAO-activated systems.