Month: December 2022

Vecchio-Sadus, Angelica M. published the artcileElectrosynthesis and magnetic behavior of neutral cobalt(II) complexes of pyridine-2-carbaldehyde pyridin-2′-ylhydrazone (papyH) and its analogs, Category: pyridine-derivatives, the publication is Transition Metal Chemistry (London) (1995), 20(1), 38-45, database is CAplus.

Neutral cobalt(II) complexes with the tridentate N-heterocyclic ligand pyridine-2-carbaldehyde pyridin-2′-ylhydrazone (papyH) and its analogs were prepared by the electrochem. oxidation of cobalt in an acetone solution of the hydrazone. [Co(papy)₂] were obtained as red-green dichroic microcrystals due to the extended π-conjugation system in the anionic ligand. The magnetic moments of the octahedral cobalt(II) chelates decrease continuously from μ_eff = 1.81-4.63 μB at room temperature to 1.7-4.08 μB at ∼90 K. The changes in magnetic moment were accounted for by a ⁴T₁ ↔ ²E spin crossover system.

Transition Metal Chemistry (London) published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C4Br2N2O4S, Category: pyridine-derivatives.

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

Updegraff, D. M. published the artcileTriarylborane complexes, a new series of broad-spectrum germicides, Application of Triphenyl(pyridin-1-ium-1-yl)borate, the publication is Journal of Infectious Diseases (1964), 304-10, database is CAplus.

More than 100 coordination complexes of triarylboranes with amines and substituted phosphines were screened against bacteria and fungi, and selected members were also screened against protozoa. The chem. stable complexes of triphenylborane and tris(para-substituted phenyl)borane were powerful broad-spectrum germicides, fungicides, and protozoicides.

Journal of Infectious Diseases published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C19H22BNO5, Application of Triphenyl(pyridin-1-ium-1-yl)borate.

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

Torssell, Kurt published the artcilePositive halogen compounds. VI. Preparation of alkoxydimethylsulfonium salts and their role in the Kornblum oxidation. Revision of the structure for the olefin-bromotrinitromethane adduct, Quality Control of 971-66-4, the publication is Acta Chemica Scandinavica (1947-1973) (1967), 21(1), 1-14, database is CAplus.

cf. CA 63: 6839b; 65: 19963b. Structure I for the reaction product of BrC(NO2)3 and cyclohexene was revised to II (R = 2-trans-bromocyclohexyl) (III). Treatment of 0.2 g. III in 1 ml. EtOAc with 0.2 g. NaBPh4 gave ROS+Me2B-Ph4 (IV, R = 2-bromocyclohexyl) (V), m. 138-40° (decomposition). III (0.2 g.) was heated with 1 ml. iso-BuOH at 55-6° 45 min. and treated with 0.2 g. NaBPh4 in 1 ml. EtOAc to give 0.19 g. IV (R = iso-Bu) (VI) m. 141-3° (decomposition). ClCO2Bu-iso prepared from 0.16 g. iso-BuOH and a slight excess of COCl2 (10% in ether) was treated, after evaporation of ether, with 1 ml. Me2SO and, after 0.5 hr., 0.7 g. NaBPh4 in 6 ml. 1:1 MeOH-water mixture to give 0.4 g. IV (R = Et), m. 150-60°, remelts ∼260°. III (1 g.) in 4 ml. MeOH kept at 40-50° 20 min., evaporated to half volume in vacuo, and treated with 10 ml. CCl4 to give 0.55 g. II (R = Me). II (R = Me) (0.25 g.) in 1 ml. MeOH was treated with 0.4 g. NaBPh4 in 1 ml. MeOH to give 0.38 g. IV (R = Me) (VII). Me2SO (0.3 g.) was mixed with 0.5 g. Me2SO4, kept at room temperature 24 hrs., treated with 0.75 g. KC(NO2)3 in 5 ml. dimethoxyethane, filtered from KMeSO4, concentrated to 0.5 volume in vacuo, and treated with 10 ml. CCl4 to give 0.3 g. VII, m. 51-2° (decomposition). Treatment of a mixture of 0.5 g. Me2SO4 and 0.3 g. Me2SO with 1.4 g. NaBPh4 in 10 ml. MeOH gave 0.9 g. VII. A bromonium ion (VIII) is suggested. VII (0.2 g.) was heated to 190° in a small bulb tube until gas evolution ceased (∼10 min.) to give 40 mg. condensate composed of benzene and MeOCH2SMe (ir and N.M.R.); the remainder was partially crystalline and gave Ph3BOSMe2 (IX), m. 160-3°. IX can also be obtained by addition of 0.1 ml. concentrated HCl to 0.2 g. NaBPh4 in 2 ml. water. Treatment of 50 mg. IX in 3 ml. EtOAc with 50 mg. pyridine gave Ph3BQ (Q = 1-pyridyl), m. 210° (decomposition), which was also obtained by Pfitzner-Moffat oxidation Pyrolysis of V at 130-40° 5 min. gave mostly benzene and a small amount IX, and pyrolysis of V in Me2SO gave a somewhat higher yield of carbonyl compounds and trans-2-bromocyclohexanol. Thus, the Kornblum oxidation and Barton’s modification (CA 61: 2958e) proceeds via an intermediary sulfonium ion, which collapses to a carbonyl compound and Me2S either by the reaction (1) or a cyclic mechanism (2), giving Me2S and CD3SCD2H when Me2CHCH2OS+(CD3)2B-Ph4 was pyrolyzed. The oxidation follows the mechanism (1) only if the α-proton is activated as in p-BrC6H4COCH2OS+Me2. A mechanism (3) for Pfitzner and Moffat oxidation (CA 64: 6709g) was suggested to proceed via a complex (X). Magnetic nonequivalence for S-methyl resonance peak of V (a doublet, separation 1.7 Hz.) was found. N.M.R. spectrum of VII or II (R = Me) underwent a drastic change when the compounds were heated in (CD3)2SO at 65°. After 1 hr., the absorption of SMe at δ = 3.29 disappeared and a new peak appeared at δ = 2.57 ppm. The peak at δ = 3.97 ppm. had the same intensity as before and only traces of Me2S were detected. The result suggested a carbonium ion exchange (4) comparable with proton exchange in water. The reaction is completely reversible because when XI was dissolved in Me2SO, VII was regenerated. Addition of NaI to VII gave a rapid change of spectrum showing a reaction, Me2SO+Me + NaI → Me2SO + MeI + Na+. Pyrolysis of VII to MeOCH2SMe resembles the Pummerer rearrangement.

Acta Chemica Scandinavica (1947-1973) published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C10H10CoF6P, Quality Control of 971-66-4.

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

Thomas, K. V. published the artcileThe environmental fate and behaviour of antifouling paint booster biocides: A review, Related Products of pyridine-derivatives, the publication is Biofouling (2001), 17(1), 73-86, database is CAplus.

A review with references Antifouling paint booster biocides are a group of organic compounds added to antifouling paints to improve their efficacy. They have become prevalent since the requirement for alternative antifouling paints formulations for small boats (<25m). This need followed a ban on the use of triorganotin biocides in antifouling paints for small boats, in the late 1980’s. Worldwide, around eighteen compounds are currently used as antifouling biocides, viz. benzmethylamide, chlorothalonil, copper pyrithione, dichlofluanid, diuron, fluorofolpet, Irgarol 1051, Sea-Nine 211, Mancozeb, Polyphase, pyridine-triphenylborane, TCMS (2,3,5,6-tetrachloro-4-methylsulfonyl pyridine), TCMTB [2-(thiocyanomethylthio)benzothiazole], Thiram, tolylfluanid, zinc pyrithione (ZPT), ziram and Zineb. Any booster biocide released into the environment is subjected to a complex set of processes. These processes include transport mechanisms, transformation, degradation, cross media partitioning, and bioaccumulation. This paper reviews the fate and behavior data currently available in the public domain concerning antifouling paint booster biocides.

Biofouling published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C5H5F3O2, Related Products of pyridine-derivatives.

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

Suzuki, Yasuyuki published the artcileReactions of 4-pyridine- and 4-quinolinesulfonic acids with amines, Synthetic Route of 18437-58-6, the publication is Yakugaku Zasshi (1961), 1146-50, database is CAplus.

4-Pyridinesulfonic acid, 4-HO₃SC₅H₄N, (I) (1.6 g.) in 16 ml. 28% NH₄OH and a small amount of ZnCl₂ in an autoclave heated 2 hrs. at 150-60° cooled, 10 ml. 2N NaOH added, the NH₄OH removed and the product extracted with CHCl₃ gave 0.65 g. 4H₂NC₅H₄N, m. 157-8°. 2,4-Me(HO₃S)C₅H₃N (3 g.), 30 ml. 28% NH₄OH and a small amount ZnCl₂ in an autoclave heated 24 hrs. at 150-60° and the product treated as above gave 1.21 g. 2,4-Me(H₂N)C₅H₃N, m. 94-5°. Similarly prepared were the following amino compounds (product, % yield, and m.p. given): 3,4-Me(H₂N)C₅H₃N, 57.2, 107.5-9.0°; 2,6,4-Me₂(H₂N)C₅H₂N, 70.8, 192-3°; [from 4-HO₃SC₉H₆N (II)] 4-H₂NC₉H₆N, 79.5, 153°. I (1.6 g.), 10 ml. 33% MeNH₂ and a small amount of ZnCl₂ heated 24 hrs. at 130° gave 0.87 g. 4-MeNHC₅H₄N; picrate, m. 122-4°. Similarly, I and Me₂NH yielded 72.5% 4-Me₂NC₅H₄N, m. 112-13° (picrate, m. 204°); II and MeNH₂ yielded 88.3% 4-MeNHC₉H₆N, m. 224°; II and Me₂NH yielded 76.3% 4-Me₂NC₉H₆N, b₁₀ 167° (picrate, m. 192°). 2-HO₃SC₅H₄N (1.6 g.), 3.2 ml. 80% N₂H₄.H₂O, 7 ml. H₂O, and a small amount of ZnCl₂ in an autoclave heated 24 hrs. at 100-5°, the solution filtered, the filtrate concentrated in vacuo, the residue in 10 ml. 50% KOH extracted with Et₂O, and the picrate formed gave 2.1 g. 2-H₂NNHC₅H₄N picrate, m. 162-3° (decomposition). Similarly prepared were the following hydrazine derivatives (starting material, product, % yield and m.p. or m.p. of its salt given): I, 4-H₂NNHC₅H₄N (III), 72, HCl salt, 242-4°; 2-HO₃SC₉H₆N, 2-H₂NNHC₉H₆N, 64.5, picrate, 187-9° (decomposition); II, 4-H₂NNHC₉H₆N (IV), 81.2, HCl salt, 3078°; 2,4-Me(HO₃S)C₉H₅N, 2,4-Me(H₂NNH)C₉H₅N, 73.3, picrate, 206° (decomposition). 4-H₂NNHC₉H₆N.HCl (0.5 g.) in 10 ml. H₂O, 2 ml. EtOH and 1 ml. 10% NaOH, while refluxing, treated dropwise with 15 ml. 10% CuSO₄, refluxed 1 hr., refluxed 1 hr. with 5 ml. 10% NaOH and the product steam distilled gave 0.25 g. C₉H₇N; picrate, m. 202-3°. III.HCl (1 g.) in 50 ml. absolute EtOH treated with EtONa (0.16 g. Na and 7 ml. EtOH), the NaCl removed, the solution concentrated to 10 ml., refluxed 1 hr. with 0.8 g. Et pyruvate and the product concentrated gave 1.05 g. Et pyruvate 4-pyridylhydrazone, columns, m. 128-30°. III.HCl (1.45 g.) in 40 ml. MeOH treated with 1 g. KSCN in 10 ml. MeOH, refluxed 9 hrs. and the product concentrated gave 1.4 g. III.HSCN, m. 1079°. III (from 1.6 g. III.HCl) in 10 ml. C₅H₅N at 0° treated dropwise with 1.55 g. BzCl, stirred 1 hr. at room temperature, kept overnight, the solvent removed, and the residue washed with H₂O gave 1.2 g. 4-pyridyldibenzoylhydrazine, m. 2345° (EtOH). III (from 1.45 g. III.HCl) in 10 ml. EtOH and 1 g. AcCH₂COMe refluxed 1 hr., the EtOH removed, the residue in 5 ml. 10% NaOH and 10 ml. H₂O extracted with CHCl₃ and the product distilled gave 1.15 g. 1-(4-pyridyl)3,5-dimethylpyrazole, b₅ 131-4°; picrate m. 237° (decomposition). A solution of 1.26 g. AcONa.3H₂O, 3 ml. H₂O, 1 g. IV.HCl, 0.37 g. Me₂CO and 1 ml. AcOH refluxed 1.5 hrs., cooled, 4 ml. H₂O added and the mixture made alk. with NH₄OH and kept overnight at 0° gave 0.62 g. acetone 4-quinolylhydrazone, m. 122°. IV (0.5 g.) in 5 ml. EtOH and 0.34 g. PhCHO refluxed 1 hr. and the product concentrated gave 0.46 g. benzaldehyde 4-quinolylhydrazone, m. 11314°. IV.HCl (0.9 g.) in 20 ml. H₂O, 0.63 g. AcONa.3H₂O and 0.4 g. pyruvic acid mixed well and the product filtered off gave 0.73 g. pyruvic acid 4-quinolylhydrazone, m. 246° (decomposition). IV (0.35 g.) in 4 ml. EtOH and 0.25 g. Et pyruvate refluxed 1 hr. and the solution concentrated gave 0.31 g. Et pyruvate 4-quinolylhydrazone, m. 178°. IV.HCl (1.4 g.), 0.7 g. KSCN, and 50 ml. MeOH refluxed 12 hrs. and the solution concentrated gave 1.2 g. IV.HSCN, m. 168-9°. IV (0.5 g.) in 5 ml. C₅-H₅N and 0.44 g. BzCl refluxed 3 hrs. and the product concentrated gave 0.37 g. 1-(4-quinolyl)-2-(benzoyl)hydrazine, m. 129.5-30.5°. IV (0.66 g.) in 5 ml. EtOH and 0.42 g. AcCH₂COMe refluxed 1 hr., the EtOH removed and the residue in 10% NaOH extracted with CHCl₃ gave 0.66 g. 1-(4quinolyl)-3,5-dimethylpyrrazole, b₄ 180-1°; picrate m. 198° (MeOH).

Yakugaku Zasshi published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C11H9ClN2O, Synthetic Route of 18437-58-6.

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

Surov, O. V. published the artcileEnthalpies of Fusion, sublimation and vaporization of some hydrazones, Quality Control of 2215-33-0, the publication is Physical Chemistry: An Indian Journal (2017), 12(1), 1-15, database is CAplus.

Enthalpies of melting, sublimation and vaporization were determined for some hydrazones. The validity of thermogravimetric procedure for measuring enthalpy of vaporization of the compounds under investigation was demonstrated. Exploring packing modes and intermol. interactions in mol. crystals of the hydrazones using Hirshfeld surfaces was carried out.

Physical Chemistry: An Indian Journal published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C5H10Cl3O3P, Quality Control of 2215-33-0.

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

Shibata, Katsumi published the artcileNiacin activity of 3-cyanopyridine, pyridine 3-sulfonic acid, nicotinic acid N-oxide, and 6-hydroxynicotinic acid in rats, Application In Synthesis of 636-73-7, the publication is Bitamin (1995), 69(7), 357-64, database is CAplus.

Niacin activity of the niacin related compounds such as 3-cyanopyridine, pyridine 3-sulfonic acid, nicotinic acid N-oxide, and 6-hydroxynicotinic acid was investigated using rats. 3-Cyanopyridine, pyridine-3-sulfonic acid, and 6-hydroxynicotinic acid had not only niacin activity but also the antagonistic activity. Nicotinic acid N-oxide had niacin activity and the relative niacin activity to nicotinic acid was about 1/2 in molar ratio.

Bitamin published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C14H10O4S2, Application In Synthesis of 636-73-7.

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

Saielli, Giacomo published the artcileOne-bond ¹J(¹⁵N-¹⁹F) spin-spin coupling constants of cationic fluorinating reagents: Insights from DFT calculations, Product Details of C6H5F4NO3S, the publication is Magnetic Resonance in Chemistry (2020), 58(6), 548-558, database is CAplus and MEDLINE.

We have investigated, by means of d. functional theory protocols, the one-bond ¹J(¹⁵N-¹⁹F) spin-spin coupling constants in a series of fluorinating reagents, containing the N-F bond, recently studied exptl. The results of the calculations show a very good linear relationship with the exptl. values, even though only the M06-2X(PCM)/pcJ-2//B3LYP/6-311G(d,p) level affords a very low mean absolute error. The calculations allow to analyze the various MOs contributions to the J coupling and to rationalize the observed pos. sign, corresponding to a neg. sign of the reduced spin-pin coupling constant K(N-F). Moreover, of the four Ramsey contributions, only the diamagnetic spin orbit is negligible, whereas the paramagnetic spin orbit and spin dipole terms decrease the magnitude of the Fermi contact (FC) term by an amount that goes from a min. of 35% up to more than 60% of the FC term itself. Several effects have been investigated, namely, the contribution of the long-range solvent reaction field, relativistic corrections, and conformational and vibrational effects.

Magnetic Resonance in 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

Profft, Elmar published the artcilePreparation and pharmacological properties of 1-(4-alkoxy-2-pyridyl)-2-ethylpiperidines, SDS of cas: 18437-58-6, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1958), 429-36, database is CAplus.

The title compounds in which the alkoxy group was MeO, EtO, PrO, BuO, iso-BuO, AmO, iso-AmO, n-C₆H₁₃O, or n-C₇H₁₅O were prepared and tested for their activity as local anesthetics by surface application of a 1% solution of their HCl salts. The PrO compound was prepared by treating 24 g. 2,4-Me(PrO)C₅H₃N with 12 g. 40% HCHO and 3 drops of HOAc at 190° for 8 h. and working up with Et₂O to give 7 g. 2,4-HOCH₂CH₂(PrO)C₅H₃N (I), yellow oil, b₁₈ 182-6°. I (10 g.) kept with 2 g. KOH for 40 h., some hydroquinone added, and the product vacuum distilled gave 2,4-CH₂:CH(PrO)C₅H₃N (II), b₂₀ 125-7°. II (0.05 mol) heated with 0.033 mol piperidine and 0.0043 mol HOAc for 3 h. on a water bath at 95-110°, then vacuum distilled gave 1-(4-propoxy-2-pyridyl)-2-ethylpiperidine, a golden oil, b₁₆ 200.5°. The other members of the series were prepared in a similar manner. Only the n-C₆H₁₃O and n-C₇H₁₅O analogs showed any significant pharmacol. activity as local anesthetics. Quaternary iodides were also prepared from the 4-alkoxy-2-methylpyridines where the alkoxy group was MeO, EtO, PrO, BuO, or AmO by treatment of 0.02 mol of the picoline with 0.021 mol MeI in 3-5 mL. EtOH for 3 h.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, SDS of cas: 18437-58-6.

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

Okuda, Shigenobu published the artcileThe constitution of matrine. XXVI. The constitution of dehydro-α-matrinidine, Safety of 4-Amino-2-picoline, the publication is Pharmaceutical Bulletin (1956), 257-61, database is CAplus.

cf. C.A. 49, 8316f. The decision between the 2 proposed structures of dehydro-α-matrinidine (I), upon which the structure of matrine depends, is based on spectrographic comparisons. Ultraviolet absorption maximum are recorded for: the degradation products of matrine, I, and the 2 bases C₁₂H₁₈N₂, m. 111° and 190°, resp.; the 4-aminopyridine group of 4-H₂N and 4-Et₂N derivatives of C₅H₅N, and 5,7-dimethyl-1,2,3,4-tetrahydro-1,6-naphthyridine (II); the 3-aminopyridine group of 3-H₂N (III) and 3-Me₂N (IV) derivatives of C₅H₅N, and 2,4-dimethyl-5,6,7,8-tetrahydro-1,5-naphthyridine (V); the 2-aminopyridine group of the 2-H₂N derivative of C₅H₅N, and 2,4-dimethyl-5,6,7,8-tetrahydro-1,8-naphthyridine. The solvents used were EtOH, 0.1N NaOH, 0.01N H₂SO₄, 50% H₂SO₄, and concentrated H₂SO₄. The spectra of 2,4-Me(H₂N) and 2,6,4-Me₂(H₂N) derivatives of C₅H₅N were determined in EtOH only. Only II and IV were previously unknown. The synthesis of II will be reported later. Methylation of III with H₂CO and HCO₂H gave IV, b₆ 95°; picrate, m. 179-81°. Study of the spectra led to the following generalizations: the 3-aminopyridine group form their di-salts even in 50% H₂SO₂, whereas the matrine products and the 4-aminopyridine group show the same absorption in 50% as in 0.01N H₃SO₃; I absorbs at much shorter wave lengths than III in EtOH, 0.1N NaOH, and 0.01N H₂SO₂; C₂H₂N₂ both have the same absorption in all solvents, very similar to that of II, and very different from that of V. It is concluded that all 3 matrine degradation compounds have the 4-aminopyridine skeleton, that I is 1-methyl-4,5,6,8,9,10-hexahydropyrido[3,4,5-ij]quinolizine, and that the C₁₂H₁₈N₂ are Me derivatives of 8-propyl-1,2,3,4-tetrahydro-1,6-naphthyridine.

Pharmaceutical Bulletin published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Safety of 4-Amino-2-picoline.

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