93560-55-5

Usage

Chemical Properties

Light yellow Cryst

InChI:InChI=1/C6H6INO/c1-9-5-3-2-4-8-6(5)7/h2-4H,1H3

Upstream product

• 40263-57-8 2-iodo-3-hydroxypyridine 
• 138-24-9 phenyltrimethylammonium chloride 
• 7295-76-3 3-methoxypyridine 
• 109-00-2 3-HYDROXYPYRIDINE 
• 24100-18-3 2-bromo-3-methoxypyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 620-08-6 4-methoxypyridine 
• 93560-59-9 3,3'-dimethoxy-2,2'-bipyridine 
• 111061-89-3 4,4'-Dimethoxy-3,3'-bipyridin 
• 111061-88-2 3,4'-Dimethoxy-2,3'-bipyridin 
• 115170-07-5 2-Iod-3-methoxy-6-nitropyridin 
• 405137-17-9 2-iodo-3-methoxypyridin-4-ol 
• 79491-44-4 2,3-Dimethoxy-6-nitropyridin 
• 36145-03-6 [2,2'-bipyridine]-3,3'-diol 
• 1233689-11-6 3-methoxy-2-[(4-methylphenyl)sulfanyl]pyridine 
• 24059-89-0 3-methoxy-pyridine-2-carbonitrile 
• 1256805-99-8 2-ethynyl-3-methoxypyridine 
• 1338920-76-5 C₁₈H₁₃NO₃ 
• 1338920-78-7 C₁₈H₁₃NO₃ 
• 1338920-77-6 C₁₁H₁₅NOSi 

Relevant academic research and scientific papers

Solid-state fluorescence of zwitterionic imidazolium pyridinolates bearing long alkyl chains: Control of emission properties based on variation of lamellar alignment

Herein, the control of the crystalline-state fluorescence of zwitterionic imidazolium 2-pyridin-3-olate 1 bearing linear alkyl chains via morphological variations is described, along with a mechanistic rationale. Crystals of 1a–e prepared from CH3CN exhibited intense blue fluorescence under UV irradiation at 298 K, whereas crystals of 1e prepared from i-PrOH/Et2O were less emissive under the same measurement conditions. Temperature-dependent emission spectra showed that emissive crystals of 1a–e experienced minimal emission decay with increasing temperature, whereas crystalline 1e, having a different polymorphism, was highly heat-quenchable. Single-crystal XRD established that less emissive, heat-quenchable crystal 1e had a lamellar structure supported by consecutive face-to-face arrangement with π-stacking interactions between imidazolium and pyridinolate moieties, whereas highly emissive, heat-resistant crystals 1d and 1e had a face-to-edge lamellar structure with CH-π interactions between the heteroaromatic rings.

Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

N-Arylation of pyrrole with 3-iodo-4-methoxypyridine was investigated by copper catalysis under different conditions. The best conditions, that proved to be protocol A (CuI, DMEDA or TMEDA, K3PO4, DMF at 110?°C) and above all protocol B (Cu2O, Cs2CO3, DMSO at 110?°C), were applied to the synthesis of various N-(methoxypyridyl) pyrroles, indoles and benzimidazoles. The behavior of the different iodinated methoxypyridines was rationalized by evaluating the partial positive charge on the carbon bearing iodine from the1H NMR chemical shift of the corresponding deiodinated substrates. The reaction was next connected with the deprotometalation-iodolysis step generating iodinated methoxypyridines: straight involvement of the crude iodo intermediates in pyrrole N-arylation afforded the expected N-(methoxypyridyl) pyrroles in good yields. Several synthesized N-(methoxypyridyl) azoles exerted low to moderate antiproliferative activity in A2058 melanoma cells.

Deprotometalation of substituted pyridines and regioselectivity-computed CH acidity relationships

A series of methoxy- and fluoro-pyridines have been deprotometalated in tetrahydrofuran at room temperature by using a mixed lithium-zinc combination obtained from ZnCl2·TMEDA (TMEDA=N,N,N′,N′-tetramethylethylenediamine) and LiTMP (TMP=2,2,6,6-tetramethylpiperidino) in a 1:3 ratio, and the metalated species intercepted by iodine. Efficient functionalization at the 3 position was observed from 4-methoxy, 2-methoxy, 2,6-dimethoxy, 2-fluoro and 2,6-difluoropyridine, and at the 4 position from 3-methoxy and 2,3-dimethoxypyridine. Interestingly, clean dideprotonation was noted from 3-fluoropyridine (at C2 and C4) and 2,6-difluoropyridine (at C3 and C5). The obtained regioselectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase (DFT B3LYP and G3MP2B3 levels) and in THF solution. In the case of methoxypyridines, the pKa values have also been calculated for complexes with LiCl and LiTMP.

A general method for copper-catalyzed arene cross-dimerization

A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bon

Preparation, X-ray structure, and reactivity of 2-iodylpyridines: Recyclable hypervalent iodine(V) reagents

2-Iodylpyridine and four examples of 3-alkoxy-2-iodylpyridines were prepared by oxidation of the respective 2-iodopyridines with 3,3-dimethyldioxirane. Structures of 2-iodylpyridine, 2-iodyl-3- isopropoxypyridine, and 2-iodyl-3-propoxypyridine were established by single-crystal X-ray diffraction analysis. 2-Iodyl-3-propoxypyridine has moderate solubility in organic solvents (e.g., 1.1 mg/mL in acetonitrile) and can be used as a recyclable reagent for oxidation of sulfides and alcohols. The reduced form of this reagent, 2-iodo-3-propoxypyridine, can be effectively separated from the reaction mixture by treatment with diluted sulfuric acid and recovered from the acidic aqueous solution by adding aqueous sodium hydroxide.

Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds

A method for regioselective cyanation of heterocycles has been developed. A number of aromatic heterocycles as well as azulene can be cyanated in reasonable to good yields by using a copper cyanide catalyst and an iodine oxidant.

Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines

Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.

One-pot iodination of hydroxypyridines

(Chemical Equation Presented) A one-pot, high-yielding iodination of hydroxypyridines and hydroxyquinolines is described. The iodination proceeds under mild conditions, and the products are obtained in high yield without the need for chromatographic purif

New syntheses of orelline and analogues via metalation and cross-coupling reactions

New total syntheses of orelline and some analogues are reported. The methodology involves metalation of 3-alkoxy-2-iodopyridines to afford 3,4-dialkoxy-2-iodopyridines, on which cross-coupling reactions are performed to reach the 2,2′-bipyridine skeleton of the alkaloid.

Notiz zur chemischen Reaktivitaet von hydroxylierten Pyridinen

Ueber mehrere Schritte werden Maltol in 3,4-Dimethoxy-2-methylpyridin (2b) und Kojisaeure in 3-Brom-4-hydroxy-5-methoxypyridin ueberfuehrt.Die Bromierung von 3,3'-Dihydroxy-2,2'-bipyridin (6) liefert ein Gemisch von Monobrom-, Dibrom-, Tribrom- und Tetrabromverbindungen 7a bis 7g, bei denen die 6-Bromderivate vorherrschen.Aehnliche Substitutionsmuster werden bei der Nitrierung von 6 erhalten, wobei die Verbindungen 7h - 7j erhalten werden.Ausgehend von 2-Iod-3-methoxypyridin (8) lassen sich die Substitutionsprodukte 10 bis 15 darstellen.Als besonders interessant erweist sich 3-Methoxy-2-iod-6-nitropyridin (11), das sich zu dem 3,3',6,6'-Tetrahydroxy-2,2'-bipyridin (16d) umwandeln laesst, einen Isomeren des Naturstoffs Orellin.