Month: November 2022

Kuivila, Henry G. published the artcileElectrophilic displacement reactions. XIV. Two novel reactions involving areneboronic acids and halogens, Application of 2-Bromo-5-methoxybenzene boronic acid, the publication is Journal of Organic Chemistry (1962), 825-9, database is CAplus.

cf. CA 56, 15531f. Bromination of m-MeOC₆H₃B(OH)₂ (I) with 1, 2, and 3 moles Br yielded 2,5-Br(MeO)C₆H₃B(OH)₂ (II), 2,4,5-Br₂(MeO)C₆H₂B(OH)₂ (III), and 2,4,5-Br₃C₆H₂OMe (IV). Chlorination gave 2,5-Cl(MeO)- C₆H₃B(OH)₂ (V) and probably 4,3-Cl(MeO)C₆H₃B(OH)₂ (VI). Reaction with ICl gave 2,5-I(MeO)C₆H₃B(OH)₂ (VII). I anhydride (2.0 g.) in 75 ml. 1:4 AcOH-H₂O treated with stirring with 2 g. NaBr and 2.39 g. Br in 25 ml. 1:4 AcOH-H₂O and the mixture refrigerated 16 hrs. yielded 90% air-dried II, dried 1 hr. at 95° to give the anhydride, m. 213-15° (H₂O), partially reverting to II on standing several months. ZnCl₂ (2 g.) and 2.15 g. II heated in the pot of a liquid-liquid extractor and refluxed with steam distillation of the oily layer gave 92% p-BrC₆H₄OMe, n²⁵_D 1.5588; sulfonamide derivative m. 150.5-1.3°. I (2 g.) dibrominated in 100 ml. 1:4 AcOH-H₂O with 4 g. NaBr and 4.78 g. Br, the mixture refrigerated 2 days, and filtered yielded 92% III monohydrate. III monohydrate (2.0 g.) in 5 ml. MeOH kept 24 hrs. with 2.5 ml. 3.873M H₂O₂, the solvent evaporated on a steam bath, the oily product extracted with petr. ether, and the residue on evaporation (2.07 g.) repeatedly recrystallized from petr. ether (Norit) yielded 19% pure 2,4,5-Br₂(MeO)C₆H₂OH, m. 68-9°. I anhydride (1 g.) and 2.5 g. NaOAc in 60 ml. 1:2 MeOH-H₂O shaken 5 min. with 3.58 g. Br, the mixture kept 5 days, the solution evaporated, and extracted with 10% NaOH gave 57% solid, recrystallized from alc. to give 0.80 g. 2,4,5-Br₃C₆H₂OMe, m. 105-6°. I (2.0 g.) in a min. of hot H₂O₂ treated with 1.41 g. AcNHCl and 5 ml. concentrated HCl and the mixture cooled to room temperature yielded 43% Cl(MeO)C₆H₃B(OH)₂, m. 115° (solidifying and m. 190-5°), recrystallized to give V anhydride, m. to 220-3°. Further cooling yielded 43% isomeric VI, m. 146-51°. Treatment of V anhydride (0.3 g.) with 3 ml. Et₂O containing 0.047 g. C₅H₅N gave a C₅H₅N complex, m. 172-5°. Similarly, 0.3 g. VI and 0.053 g. C₅H₅N in Et₂O gave a complex, m. 156-9°. V (or VI) anhydride (2 g.) and 2 g. ZnCl₂ in 15 ml. H₂O refluxed 19 hrs. in a liquid-liquid extractor and the distilled ClC₆H₄OMe dried over KOH gave infrared spectra identical with those of o- and p-ClC₆H₄OMe, resp. V-VI (1 g.) treated with 2 g. (HOCH₂CH₂)₂NH and the complex, ν 3140 cm.^-1, hydrolyzed with dilute HCl and aqueous ZnCl₂ gave only p-ClC₆H₄OMe. I anhydride (2 g.) in 70 ml. CCl₄ heated 15 min. on a steam bath with 2.8 g. ICl in 20 ml. CCl₄, the refrigerated mixture filtered, the filtrate titrated with thiosulfate to show the use of 25% of ICl in chlorination and 50% in iodination, and the precipitate recrystallized repeatedly from CCl₄ gave 0.77 g. VII anhydride, m. 84-7°, neutralization equivalent 260 (with conversion to p-IC₆H₄OMe, m. 51-3°). The anhydride reverted readily to VII. The initial filtrate yielded 0.38 g. crude Cl(MeO)C₆H₃B(OH)₂ anhydrides. H₂O (50 ml. containing 4.0 g. NaOH and 10 millimoles Br treated with 10 millimoles PhB(OH)₂ with consumption in 15 min. of 4.9 millimoles Br for substitution and 5.1 millimoles in oxidation, the mixture acidified, and filtered yielded 20% 2,4,6-Br₃C₆H₂OH (VIII), m. 79.5-82.5°. NaOBr (19.5 millimoles) in 50 ml. H₂O kept 1 hr. with 4.88 millimoles PhB(OH)₂ in 20 ml. H₂O, acidified with HNO₂, filtered, and the air-dried precipitate (1.3 g.) treated with 5 ml. alc. gave 0.8 g. insoluble unidentified compound, m. gradually above 180°. Dilution of the filtrate with H₂O yielded 28% VIII. Br (15 millimoles) and 28 millimoles NaOH in 10 ml. H₂O kept 1 hr. with 5 millimoles p-BrC₆H₄B(OH)₂ and the product acidified yielded 78% VIII. PhB(OH)₂ (9.63 millimoles) in 5 ml. H₂O treated with 40.45 millimoles NaOCl in 75 ml. H₂O, the solution heated 1 hr. at 80°, the cooled solution treated with 1 g. NaHSO₃, acidified, filtered, and the product steam distilled yielded 90% 2,4,6-Cl₃C₆H₂OH, m. 67.5-8.0; p-nitrobenzoate m. 103.5-5.0°. Repetition with equimolar amounts of NaOCl and PhB(OH)₂ and distillation yielded 80% PhOH, b. 182-7°; p-nitrobenzoate corresponding to that of PhOH. NaOCl (10 millimoles) and 10 millimoles PhB(OH)₂ in 25 ml. H₂O heated 30 min. at 80° and the product analyzed for Cl showed that 8.11 millimoles NaOCl had been used for oxidation but only 1.89 millimoles for nuclear chlorination.

Journal of Organic Chemistry published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Application of 2-Bromo-5-methoxybenzene boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mozhenok, T. P. published the artcileEffects of some DNA-intercalators and antioxidative compounds on the phagosome-lysosome fusion and F-actin content in murine peritoneal macrophages, Product Details of C20H18BrN3, the publication is Tsitologiya (1998), 40(6), 585-590, database is CAplus.

Effect of DNA-intercalators ethidium bromide (EB, 0.005 and 0.015 mM) and dimidium bromide (DB, 0.005 and 0.010 mM) and antioxidative compounds acetylsalicylic acid (ASA, 0.05 and 0.50 mM) and β-carotene (0.01, 0.02, 0.05 mM) on the phagosome-lysosome (P-L) fusion and F-actin content in murine peritoneal macrophages were studied. EB, DB, ASA and β-carotene were found to stimulate P-L fusion and the effect depending on the concentration of compounds tested. The strongest influence was evoked by 0.5 mM of ASA and 0.05 mM of β-carotene. The compounds tested enhanced F-actin content in macrophages, especially by the action of β-carotene (0.05 mM). The obtained data indicate a correlation between P-L fusion stimulation and F-actin content under the influence of compounds tested in murine peritoneal macrophages.

Tsitologiya published new progress about 518-67-2. 518-67-2 belongs to bromides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Salt,Amine,Benzene, name is Dimidium bromide, and the molecular formula is C20H18BrN3, Product Details of C20H18BrN3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Dolbois, Aymeric published the artcile1,4,9-Triazaspiro[5.5]undecan-2-one Derivatives as Potent and Selective METTL3 Inhibitors, Formula: C7H5Br2F, the publication is Journal of Medicinal Chemistry (2021), 64(17), 12738-12760, database is CAplus and MEDLINE.

N⁶-methyladenosine (m⁶A) is the most frequent of the 160 RNA modifications reported so far. Accumulating evidence suggests that the METTL3/METTL14 protein complex, part of the m⁶A regulation machinery, is a key player in a variety of diseases including several types of cancer, type 2 diabetes, and viral infections. Here we report on a protein crystallog.-based medicinal chem. optimization of a METTL3 hit compound that has resulted in a 1400-fold potency improvement (IC₅₀ of 5 nM for the lead compound 22 (UZH2)(I) in a time-resolved Forster resonance energy transfer (TR-FRET) assay). The series has favorable ADME properties as physicochem. characteristics were taken into account during hit optimization. UZH2 shows target engagement in cells and is able to reduce the m⁶A/A level of polyadenylated RNA in MOLM-13 (acute myeloid leukemia) and PC-3 (prostate cancer) cell lines.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mondal, Rajib published the artcileThiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications, Related Products of bromides-buliding-blocks, the publication is Journal of Materials Chemistry (2010), 20(28), 5823-5834, database is CAplus.

Thiophene enriched fused-aromatic thieno[3,4-b]pyrazine systems were designed and employed to produce low band gap polymers (E_g = 1.0-1.4 eV) when copolymerized with fluorene and cyclopentadithiophene. The copolymers are mainly investigated for organic thin film transistor and organic photovoltaic applications. Mol. packing in the thin films of these polymers was investigated using Grazing incidence X-ray Scattering. Although both fluorene and cyclopentadithiophene polymers follow similar face to face π-π stacking, the latter polymers show much smaller lamellar d-spacings due to side-chain interdigitation between the lamellae. This lead to the higher charge carrier mobilities in cyclopentadithiophene polymers (up to 0.044 cm2/V.s) compared to fluorene polymers (up to 8.1 × 10^-3 cm²/V.s). Power conversion efficiency of 1.4% was achieved using fluorene copolymer in solar cells with a fullerene derivative as an acceptor. Although the cyclopentadithiophene polymers show lower band gaps with higher absorption coefficients compared to fluorene copolymers, but the power conversion efficiencies in solar cells of these polymers are low due to their low ionization potentials.

Journal of Materials Chemistry published new progress about 52431-30-8. 52431-30-8 belongs to bromides-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 2,5-Dibromo-3,4-dinitrothiophene, and the molecular formula is C4Br2N2O4S, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Gujadhur, Rattan K. published the artcileFormation of Aryl-Nitrogen, Aryl-Oxygen, and Aryl-Carbon Bonds Using Well-Defined Copper(I)-Based Catalysts, Computed Properties of 25753-84-8, the publication is Organic Letters (2001), 3(26), 4315-4317, database is CAplus and MEDLINE.

The authors report mild synthetic protocols for the formation of aryl-carbon, aryl-nitrogen, and aryl-oxygen bonds based on soluble, well-defined copper(I) catalysts. These protocols do not require the use of palladium and/or expensive ligands. E.g., Cu(Phen)(PPh₃)Br catalyzed the coupling of PhCCH with PhI to give 80% PhCCPh.

Organic Letters published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C30H24BrCuN2P, Computed Properties of 25753-84-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sosnowska, Anita published the artcilePredicting enthalpy of vaporization for Persistent Organic Pollutants with Quantitative Structure-Property Relationship (QSPR) incorporating the influence of temperature on volatility, Application of 1,3-Dibromonaphthalene, the publication is Atmospheric Environment (2014), 10-18, database is CAplus.

Enthalpy of vaporization (ΔH_vap) is a thermodn. property associated with the dispersal of Persistent Organic Pollutants (POPs) in the environment. Common problem in the environmental risk assessment studies is the lack of exptl. measured ΔH_vap data. This problem can be solved by employing computational techniques, including QSPR (Quant. Structure-Property Relationship) modeling to predict properties of interest. Majority of the published QSPR models can be applied to predict the enthalpy of vaporization of compounds from only one, particular group of POPs (i.e., polychlorinated biphenyls, PCBs). We have developed a more general QSPR model to estimate the ΔH_vap values for 1436 polychlorinated and polybrominated benzenes, biphenyls, dibenzo-p-dioxins, dibenzofurans, di-Ph ethers, and naphthalenes. The QSPR model developed with Multiple Linear Regression anal. was characterized by satisfactory goodness-of-fit, robustness and the external predictive performance (R² = 0.888, Q²_CV = 0.878, Q²_Ext = 0.842, RMSE_C = 5.11, RMSE_CV = 5.34, RMSE_P = 5.74). Moreover, we quantified the temperature dependencies of vapor pressure for twelve groups of POPs based on the predictions at six different temperatures (logP_L(T)). In addition, we found a simple arithmetic relationship between the logarithmic values of vapor pressure in pairs of chloro- and bromo-analogs. By employing this relationship it is possible to estimate logP_L(T) for any brominated POP at any temperature utilizing only the logP_L(T) value for its chlorinated analogs.

Atmospheric Environment published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C7H5ClN2S, Application of 1,3-Dibromonaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Balthazar, Zsolt published the artcileTwo-phase titration of anionic surfactants, I. Study of the transition point of the titration carried out according to ISO 2271, Formula: C20H18BrN3, the publication is Magyar Kemiai Folyoirat (1977), 83(7), 294-7, database is CAplus.

Some properties of the Disulphine Blue [64366-33-2]-dimidium bromide [518-67-2] indicator system, prescribed by the international standard, were examined by UV-visible spectrometry. The dyes appeared in the CHCl3 phase only in the presence of an oppositely charged surfactant. In the modeling of practical end-points, the absorbance of the CHCl3 phase was markedly influenced by the presence of an anionic or cationic surfactant. The titration end-point determined photometrically using the 2 indicators was identical within exptl. error.

Magyar Kemiai Folyoirat published new progress about 518-67-2. 518-67-2 belongs to bromides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Salt,Amine,Benzene, name is Dimidium bromide, and the molecular formula is C20H18BrN3, Formula: C20H18BrN3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Dymock, Brian W. published the artcileNovel, Potent Small-Molecule Inhibitors of the Molecular Chaperone Hsp90 Discovered through Structure-Based Design, Safety of Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, the publication is Journal of Medicinal Chemistry (2005), 48(13), 4212-4215, database is CAplus and MEDLINE.

The crystal structure of a previously reported screening hit 1 (CCT018159) bound to the N terminal domain of mol. chaperone Hsp90 has been used to design 5-amide analogs. These exhibit enhanced potency against the target in binding and functional assays with accompanying appropriate cellular pharmacodynamic changes. Compound 11 (VER-49009) compares favorably with the clin. evaluated 17-AAG.

Journal of Medicinal Chemistry published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, Safety of Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Heuser, Stefan published the artcileSynthesis of novel cyclopropylic sulfones and sulfonamides acting as glucokinase activators, HPLC of Formula: 18928-94-4, the publication is Tetrahedron Letters (2006), 47(16), 2675-2678, database is CAplus.

A synthetic route towards cyclopropylic compounds, which act as glucokinase activators is described herein. The present synthesis gives easy and rapid access to a wide variety of either sulfones or sulfonamides starting from readily available late-stage intermediates.

Tetrahedron Letters published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C7H13Br, HPLC of Formula: 18928-94-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Kratzer, Domenic published the artcileSynthetic Route to Sulfobetaine Methacrylates with Varying Charge Distance, Safety of Sodium 3-bromopropane-1-sulfonate, the publication is European Journal of Organic Chemistry (2014), 2014(36), 8064-8071, database is CAplus.

A general synthetic strategy is described that enables access to a library of new sulfobetaine methacrylates starting from com. available precursors. The three-step procedure allows the distance between the quaternary amine and the sulfonate group (inner charge distance) to be varied by selecting the corresponding dibromoalkane in the first step. A key step is the final esterification, in which methacrylic acid acts as solvent as well as reagent for the zwitterionic hydroxy intermediates. Thus, it is possible to synthesize monomeric precursors with up to twelve methylene groups between the pos. and the neg. charge. A selection of these monomers has been successfully tested for their ability to polymerize using free-radical polymerization

European Journal of Organic Chemistry published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Safety of Sodium 3-bromopropane-1-sulfonate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary