Tag: M.W=200-250

Umemoto, Teruo published the artcileN-Fluoropyridinium triflate and its analogs. The first stable 1:1 salts of pyridine nucleus and halogen atom, Application In Synthesis of 107263-95-6, the publication is Tetrahedron Letters (1986), 27(28), 3271-4, database is CAplus.

N-Fluoropyridinium salts having non-nucleophilic counter-anions, e.g., I (R = F, R¹-R⁵ = H; R = F, R¹ = Me, R²-R⁵ = H; X = CF₃SO₃), and their derivatives were synthesized by treating pyridine-F₂ adducts with strong Broensted acids, their salts, or trimethylsilyl esters, or Lewis acids, or by allowing F₂ to react with N-trimethylsilylpyridinium salts I (R = SiMe₃).

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C7H7IN2O, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileN-Fluoropyridinium triflate: an electrophilic fluorinating agent, Safety of 1-Fluoropyridiniumtriflate, the publication is Organic Syntheses (1990), 129-43, database is CAplus.

The title compound (I) was prepared by fluorination of pyridine with F₂ in MeCN in the presence of CF₃SO₃Na. Treating methoxy(trimethylsiloxy)estratetraene II with I in CHCl₂ gave 66% the 16α-fluoroestrone III. A variety of examples of the use of I and its derivatives are also described.

Organic Syntheses published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C10H12F6N4O6PdS2, Safety of 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileNovel base-initiated reactions of N-substituted pyridinium salts, COA of Formula: C6H5F4NO3S, the publication is Journal of Fluorine Chemistry (1996), 77(2), 161-168, database is CAplus.

Reaction of N-fluoropyridinium triflate with a base in dichloromethane gave 2-chloropyridine as the major product along with 2-pyridyl triflate and 2-fluoropyridine, regardless of the nature of the base. This base-initiated reaction was also shown to take place similarly in other halogenated alkanes, ethers, a nitrile, aromatics, a ketone, vinyl ethers, alcs. and trimethylsilyl acetate as solvents to give pyridine derivatives substituted with a solvent mol.(s) at the 2-position. N-(Trifluoromethanesulfonyloxy)- and (benzenesulfonyloxy)pyridinium salts were found to undergo the same base-initiated reaction. These reactions may be explained by a postulated singlet carbene produced through proton abstraction of N-substituted pyridinium salts. A similar carbene reaction may thus likely occur in the thermal decomposition of thiatriazole. The ab initio MO calculations revealed the structure and properties of the labile deprotonated N-fluoropyridinium cation and supported the carbene intermediate reaction mechanism rather than a pyridynium or pyridyl cation mechanism. Quarroz’s reports on the reactions of picolinic acid N-oxide and the reported reactions of pyridines with F₂, CH₃COOF or CsSO₄F in solvents may be explained by this carbene mechanism.

Journal of Fluorine Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C9H21NO3, COA of Formula: C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileα-Fluorination of sulfides with N-fluoropyridinium triflates, HPLC of Formula: 107263-95-6, the publication is Bulletin of the Chemical Society of Japan (1986), 59(11), 3625-9, database is CAplus.

The reaction of RSCH₂R¹ [I R = Ph, PhCH₂, C₆H₄Cl-4, Me, dodecyl; R¹ = H, CO₂Et, CO₂Me, CH₂CH(CO₂Me)NHCOCF₃] with N-fluoropyridium salts II (X = CF₃SO₃, BF₄), III, and IV was examined While the fluorinating power increased in the order of II (X = CF₃SO₃) < III < IV, the yield of α-fluoro sulfide decreased in the order of II > III, and IV no longer produced the α-fluoro sulfide. II (X = CF₃SO₃) was more reactive than II (X = BF₄). Thus, RSCHFR¹ were prepared by α-fluorination of I with II (X = CF₃SO₃) under mild conditions. RS(O)_nCHFR¹ (n = 1, 2) were easily prepared by α-fluorination of I with II, followed by oxidation

Bulletin of the Chemical Society of Japan published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C8H15ClN2, HPLC of Formula: 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yokoyama, Yasuo published the artcileThe development of a novel synthetic method for cyanofluoroamides using a cobaltadithiolene complex, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Synthesis (2004), 701-705, database is CAplus.

N,N-Di-Et 2-cyano-2-fluoro-2-(phenylthio)acetamide reacted with germyl anion species to give the corresponding enolate. When this enolate was treated with an unsaturated organic halide, in the presence of a catalytic amount of cobaltadithiolene I, II was obtained in good yield. Interestingly, in the absence of I, no target product was obtained. This reaction proceeded smoothly under mild reaction conditions and only cyanofluoroamide was obtained.

Synthesis published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C17H14F3N3O2S, Recommanded Product: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Fujisawa, Hidehito published the artcileSimple procedure for preparation of α-fluoro esters by fluorination of ester enol silyl ethers with perchloryl fluoride, Application In Synthesis of 107263-95-6, the publication is Journal of Fluorine Chemistry (2002), 117(2), 173-176, database is CAplus.

A practical method for general preparation of α-fluoro esters by fluorination of the corresponding enol silyl ethers using diluted FClO₃ in the presence of suitable amount of amine is described. Fluorination of ester enol silyl ethers in THF at room temperature using diluted perchloryl fluoride (FClO₃) in the presence of ca. 0.5 M eq. of t-BuNH₂ as an additive produced the corresponding α-fluoro esters in over 80% yields. For example, fluorination of [(1-ethoxy-2-phenylethenyl)oxy]trimethylsilane with perchloryl fluoride gave α-fluorobenzeneacetic acid Et ester.

Journal of Fluorine Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Talik, Zofia published the artcile2,6-Dimethyl-3-fluoro-4-nitropyridine N-oxide, Category: pyridine-derivatives, the publication is Roczniki Chemii (1965), 39(4), 601-6, database is CAplus.

Reactivity of the fluorine atom in I was found to be lower than in the 3-fluoro-4-nitropyridine N-oxide. A series of substitution reactions of F or NO₂-group was carried out. A mixture of 25 g. 2,6-dimethyl-3-aminopyridine in 150 ml. EtOH, 150 ml. HBF₄, prepared from 140 ml. 48% HF and 45 g. H₃BO₃, was treated at 0°, during 90 min. with EtONO, kept 10 min. at 50°, cooled to 0°, treated again during 2 hrs. with EtONO, and distilled under reduced pressure to remove EtOH. The residue was made alk. with aqueous KOH and steam-distilled The distillate saturated with NaCl and extracted with Et₂O gave 11 g. 2,6-dimethyl-3-fluoropyridine (II), b. 136-8°. A cold solution of 25 g. II in 150 ml. Ac₂O was treated with 150 ml. 30% H₂O₂, left for a few hrs. at room temperature, then kept 30 hrs. at 60° and distilled under reduced pressure to remove AcOH and AcOOH. The whole was dissolved, below 10° in 30 ml. concentrated H₂SO₄ and 30 ml. 20% oleum, then added carefully to 60 ml. 20% oleum and 90 ml. HNO₃ (d. 1.52), kept 1 hr. on a water bath, poured onto 300 g. ice, and neutralized with solid (NH₄)₂CO₃ to give 24 g. I, m. 136° (H₂O). I (1 g.) and 30 ml. alc. NH₃, saturated at 0°, was autoclaved 4 hrs. at 120-30° and evaporated to dryness. The residue triturated with small amount H₂O, cooled, and filtered gave 0.8 g. 2,6-dimethyl-3-amino-4-nitropyridine N-oxide (III), m. 189-90° (H₂O). III (0.4 g.), 1 ml. PCl₃, in 15 ml. CHCl₃ was refluxed 1 hr., evaporated, and the residue neutralized with aqueous KHCO₃ to afford 0.3 g. 2,6-dimethyl-3-amino-4-nitropyridine, m. 112° (H₂O). III (0.3 g.) reduced in 10 ml. of boiling AcOH with 0.6 g. Fe dust, kept 30 min. on a water bath, made alk. with 50% KOH, and extracted with Et₂O gave 0.2 g. 2,6-dimethyl-3,4-diaminopyridine, m. 181° (C₆-H₆-EtOH); picrate m. 215°. Similarly, reduction of 1 g. I with 2 g. Fe in 25 ml. AcOH afforded 0.7 g. 2,6-dimethyl-3-fluoro-4-aminopyridine, m. 92° (H₂O); picrate m. 235° (alc.). Heating of 0.5 g. I and 5 ml. PhNH₂ during 2 hrs. at 120-30°, followed by pouring into H₂O and acidifying with HCl, yielded 90.3% 2,6-dimethyl-3-phenylamino-4-nitropyridine N-oxide, m. 146° (EtOH-H₂O). A solution of 1.5 g. KOH in 13 ml. H₂O, treated successively with 2 ml. 30% H₂O₂ and 1 g. I, kept 30 min. on a water bath, cooled, and filtered, gave 0.8 g. 2,6-dimethyl-8-hydroxy-4-nitropyridine N-oxide, m. 99° (H₂O). A mixture of 1 g. I and MeONa, prepared from 0.15 g. metallic Na and 20 ml. MeOH, refluxed 1 hr., evaporated, and extracted with CHCl₃, afforded 0.9 g. 2,6-dimethyl-3-methoxy-4-nitropyridine N-oxide, m. 137° (H₂OEtOH). Similarly, substitution of F atom in I using EtONa yielded 94.2% 2,6-dimethyl-3-ethoxy-4-nitropyridine N-oxide, m. 103° (aqueous alc.). I (5 g.) refluxed 1 hr. with 10 ml. PCl₃ in 10 ml. CHCl₃, evaporated, and the residue decomposed with ice and neutralized with Na₂CO₃ was steam-distilled to give in the distillate 2.5 g. 2,6-dimethyl-3-fluoro-4-chloropyridine, b. 174-5°; picrate m. 125° (alc.). Similarly, I and PBr₃ yielded 54.7% 2,6-dimethyl-3-fluoro-4-bromopyridine, m. 67° (ligroine); picrate m. 140° (alc.).

Roczniki Chemii published new progress about 3726-08-7. 3726-08-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Fluoride,Bromide, name is 4-Bromo-3-fluoro-2,6-dimethylpyridine, and the molecular formula is C17H20ClN3, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Talik, T. published the artcileReactivity of fluoronitropyridines. II. Derivates of fluoronitropyridines, Related Products of pyridine-derivatives, the publication is Bulletin de l’Academie Polonaise des Sciences, Serie des Sciences Chimiques (1968), 16(1), 7-12, database is CAplus.

Fluoronitropyridines and their derivatives were prepared as previously described (T. Talik and Z. Talik, 1964-7). Their reactivity could be compared as follows: 3,5-dinitro-2-fluoropyridine > 3-fluoro-4-nitropyridine N-oxide > 3-fluoro-5-methyl-4-nitropyridine N-oxide > 2-fluoropyridines with a Me group in the 3, 4, 5, or 6 position and a nitro group in the 3 or 5 position > 3-fluoro-4-nitropyridine > 3-fluoro-2-methyl-4-nitropyridine N-oxide > 2-fluoro-4-nitropyridine > 2,6-dimethyl-3-fluoro-4-nitropyridine N-oxide.

Bulletin de l’Academie Polonaise des Sciences, Serie des Sciences Chimiques published new progress about 3726-08-7. 3726-08-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Fluoride,Bromide, name is 4-Bromo-3-fluoro-2,6-dimethylpyridine, and the molecular formula is C6H17NO3Si, Related Products of pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Kiselyov, Alexander S. published the artcileA highly regioselective reaction of N-fluoropyridinium salts with stabilized sulfur, oxygen, and nitrogen nucleophiles: a convenient route to 2-substituted pyridines, HPLC of Formula: 107263-95-6, the publication is Journal of Heterocyclic Chemistry (1993), 30(5), 1361-4, database is CAplus.

2-Substituted pyridines I (R = phenoxy, phenylthio, imidazolyl, triazolyl, etc.) are efficiently obtained by the reactions of N-fluoropyridinium salts II (X = tetrafluoroborate, triflate) with anions derived from benzenethiols, phenols, azoles, cyanamide, and with azide anion. The results are consistent with a nucleophile addition at the position 2 of the N-fluoropyridinium cation as the major reaction pathway. The Reissert-Henze reaction of N-methoxypyridinium perchlorate to give I was unsuccessful.

Journal of Heterocyclic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, HPLC of Formula: 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Kiselyov, Alexander S. published the artcileSynthesis of 2-substituted pyridines by the reaction of N-fluoropyridinium fluoride with trimethylsilyl derivatives, Product Details of C6H5F4NO3S, the publication is Journal of Organic Chemistry (1993), 58(16), 4476-8, database is CAplus.

A 1-pot preparation of 2-substituted pyridines in the reaction of N-fluoropyridinium fluoride generated in situ with C-, O- and N-(trimethylsilyl) compounds in the presence of a catalytic amount of Bu₄NF is described. Treatment of 1-fluoropyridinium fluoride with Et (trimethylsilyl)acetate gave Et 2-pyridineacetate (I) in 55% yield.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Product Details of C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem