Author: Jessica.F

Durka, Krzysztof published the artcileThe Influence of Boronate Groups on the Selectivity of the Br-Li Exchange in Model Dibromoaryl Boronates, Product Details of C7H8BBrO2, the publication is European Journal of Organic Chemistry (2013), 2013(15), 3023-3032, database is CAplus.

The selectivity of the Br/Li exchange reaction of 6-butyl-2-(2,5-dibromophenyl)-1,3,6,2-dioxazaborocane (2,5-Br₂C₆H₃B(OCH₂CH₂)₂NBu) and the analogous anionic derivatives, 2,5-Br₂C₆H₃B(OiPr)₃Li and 2,5-Br₂C₆H₃BF₃K, was studied using BuLi as the lithiating reagent. In the case of the former compound there was a slight preference for lithiation at the 5-position. For 2,5-Br₂C₆H₃B(OiPr)₃Li, the lithiation occurred exclusively at C5, but for 2,5-Br₂C₆H₃BF₃K, 2-lithiation was preferred. Calculations performed for the lithiation of ortho- and meta-brominated Ph boronates revealed that ortho-lithiated aryl boronates are thermodynamically more stable, but that the Br/Li exchange is generally dictated by kinetics, which accounts for the variation of selectivity depending on the type of boronate group. The successful generation of the 2,5-dilithiophenyl boronate species 2,5-Li₂C₆H₃B(OCH₂CH₂)₂NBu by a double Br/Li interconversion is reported. The Br/Li exchange in the related 6-butyl-2-[3-(2,5-dibromothienyl)]-1,3,6,2-dioxazaborocane, 2,5-Br₂-3-ThB(OCH₂CH₂)₂NBu, occurred preferentially at the 5-position, but the product was readily transformed into the more stable 2-lithiated isomer. The use of 2 equiv of BuLi resulted in the efficient formation of the dilithiated species, 2,5-Li₂-3-ThB(OCH₂CH₂)₂NBu. The obtained lithiated aryl boronates were converted into functionalized arylboronic acids by treatment with selected electrophiles.

European Journal of Organic Chemistry published new progress about 1450711-53-1. 1450711-53-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (2-Bromo-5-methylphenyl)boronic acid, and the molecular formula is C7H8BBrO2, Product Details of C7H8BBrO2.

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

Lepeltier, Marc published the artcileNew azaborine-thiophene heteroacenes, Quality Control of 52431-30-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2010), 46(37), 7007-7009, database is CAplus and MEDLINE.

A new class of heteroacenes containing B, N and S elements in the 22-electron aromatic nucleus was synthesized by reaction of diaminoterthiophenes with dichlorophenylborane. Their structure was studied by x-ray crystallog. and DFT calculations UV-visible absorption /emission spectroscopy shows high rigidity and deep-blue fluorescence of these compounds

Chemical Communications (Cambridge, United Kingdom) 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, Quality Control of 52431-30-8.

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

Arbuzov, B. A. published the artcileAction of triethyl phosphite and diethyl sodium phosphite on some dihalo derivatives, Application In Synthesis of 594-81-0, the publication is Zhurnal Obshchei Khimii (1951), 99-107, database is CAplus.

To (EtO)₂PONa (from 44.2 g. ester and 7.2 g. Na) in 450 ml. dry Et₂O was added 28.5 g. ClCH₂CH₂CN, b₁₀ 63-5°, n²⁰_D 1.4370, d²⁰₂₀ 1.1461, over 0.5 hr.; after refluxing 1 hr., the filtrate yielded 42.7 g. (70.2%) (EtO)₂P(O)CH₂CH₂CN, b₇ 150-2°, b₂ 127-8°, n²⁰_D 1.4380, d²⁰₂₀ 1.1127; this (9.9 g.) heated 8 hrs. to 115-30° in a sealed tube with 30 ml. 2:1 HCl and evaporated gave 6.2 g. (78.5%) (HO)₂P(O)CH₂CH₂CO₂H, m. 166° (by Soxhlet extraction with dry C₆H₆, then with dry Me₂CO). Addition of 40.6 g. BrCH₂CHBrCN, b₁₀ 89-90°, n²⁰_D 1.5390, d²⁰₂₀ 2.0955, to (EtO)₂PONa (from 53.3 g. ester and 8.7 g. Na) in 500 ml. Et₂O and treatment as above gave after repeated fractionation 7 g. (11.9%) (EtO)₂POH, b₇ 60-5°, n²⁰_D 1.4080, d²⁰₂₀ 1.0667, and 9.5 g. (26.4%) (EtO)₂P(O)C(CN):CH₂ or (EtO)₂P(O)CH:CHCN, b₁ 124-7°, n²⁰_D 1.4360, d²⁰₂₀ 1.1277, soluble in H₂O and reacting rapidly with Br water or KMnO₄; hydrolysis with 1:1 HCl 10 hrs. at 150-65° gave on evaporation a mixture of products, which, on removal of NH₄Cl by addition of dry EtOH and evaporation of the extract, gave 4 g. oil; this with BaCO₃ gave a mixture of Ba salts, from which was isolated a H₂O-insoluble Ba salt, possibly C₆H₄P₂O₁₁Ba₃, BaHPO₄, or Ba phosphonoacrylate; a considerable amount of H₂O-soluble C₆H₈O₁₀P₂Ba was also isolated. The products were not identified further. Addition of 32.8 g. (EtO)₃P to 20.2 g. BrCH₂CHBrCN over 0.5 hr. led to a temperature rise to 87°, where it was kept for removal of the EtBr; after 15 min. at 150°, the mixture yielded a total of 19 g. EtBr, but distillation of the residue failed to yield definite products. Addition of 16.1 g. PhCH:CHBr, b₁₀ 88-90°, n²⁰_D 1.6018, d²⁰₂₀ 1.4094, to (EtO)₂PONa (from 13.1 g. ester and 2 g. Na) in 100 ml. MePh (in Et₂O the reaction does not occur) gave no immediate NaBr, but after a 4-hr. reflux 6.6 g. NaBr precipitated and fractionation of the solution gave 7.1 g. (44%) original bromide and 1.9 g. (12%) PhCH(PO₃Et₂)CH₂P(O)(OEt)₂, b₁ 181°, n²⁰_D 1.4920, d²⁰₂₀ 1.1524, which on hydrolysis 7 hrs. at 120-30° with 1:1 HCl gave the free diphosphonic acid, m. 212-14° (from H₂O). Possibly, both phosphono groups are attached to the terminal C atom, but no further characterization was attempted. PhCH:CHBr (14.9 g.) added to 14.5 g. (EtO)₃P at 200-10° did not react and practically all the (EtO)₃P was recovered; heating the components 8 hrs. to 180-200° in a sealed tube gave only traces of high-boiling products. Addition of 34.6 g. PhCHBrCH₂Br in Et₂O over 35 min. to (EtO)₂PONa (from 37.5 g. ester and 6 g. Na) in 500 ml. Et₂O, gave a precipitate of NaBr and, after refluxing 2 hrs., 6.3 g. (53.7%) styrene, about 12 g. (EtO)₂POH, 4.8 g. unreacted dibromide, and about 14 g. of a fraction b₁₁ 90-132°, which on redistillation gave a liquid, b₃ 105-130°; this with 2-C₁₀H₇NH₂ gave 1.2 g. (EtO)₂P(O)NHC₁₀H₇-2, m. 69°, which indicated that the high-boiling liquid was probably (EtO)₂POP(O)(OEt)₂ (cf. Arbuzov and Arbuzov, C.A. 25, 3618). Addition of 22 g. (EtO)₃P over 1 hr. to 16 g. PhCHBrCH₂Br preheated to 155-60° and heating 1 hr. to 165-70° gave 8.6 g. EtBr, 4.7 g. (50.2%) styrene, 3.8 g. crude (EtO)₂POH, b₁₁ 69-72°, 1.7 g. unreacted dibromide, and 10.3 g. crude liquid, b₂ 103-57°, which on redistillation gave a product, b₂ 117-31°, forming with 2-C₁₀H₇NH₂, 0.8 g. (EtO)₂P(O)NHC₁₀H₇, corresponding to a 4.8% yield of tetra-Et subphosphate. When PhCHBrCH₂Br is heated alone to 155-70°, much HBr forms, thus explaining the formation of (EtO)₂POH above. Heating 9.2 g. dibromide to 195-205°, gradual addition of 10.2 g. (EtO)₂POH, and heating 1 hr. to 210-15° gave 4.1 g. EtBr and about 1.5 g. styrene (crude). Addition of 21.4 g. PhCMe:CHBr, b₁₁ 103-5°, n²⁰_D 1.5880, d²⁰₂₀ 1.3790, to (EtO)₂PONa (from 16 g. ester and 2.5 g. Na) in 200 ml. Et₂O and refluxing 1 hr. gave 2.1 g. unreacted bromide and 4 g. (16%) PhCMe:CHP(O)(OEt)₂, b₁ 146-9°, n²⁰_D 1.5210, d²⁰₂₀ 1.1094, which immediately reacts with Br; hydrolysis by 1:1 HCl 6 hrs. at 135-45° in a sealed tube and evaporation gave some crude PhCMe:CH₂ and H₃PO₄, isolated as the PhNHNH₂ salt, m. 155° (from EtOH). Addition over 40 min. of 12.5 g. (EtO)₃P to 13.6 g. PhCMe:CHBr preheated to 150-60° and heating 1 hr. to 165-70° gave 2.3 g. EtBr, 2.1 g. unreacted bromide, 3.1 g. (EtO)₂POH, and 5 g. (33.5%) PhCMe:CHP(O)(OEt)₂, b_1.5 149-50°, n²⁰_D 1.5190, d²⁰₂₀ 1.1009, which on hydrolysis with 1:1 HCl at 120-30° cleaves into H₃PO₄ and PhCMe:CH₂. PhCMeBrCH₂Br (30.6 g.) with (EtO)₂PONa (from 33 g. ester and 5.3 g. Na) in 400 ml. Et₂O, refluxed 2 hrs., gave 5.9 g. (45.4%) PhCMe:CH₂ and apparently about 6 g. (EtO)₂POH; no individual substances of higher b.p. were identified. (EtO)₂PONa with (Me₂CBr)₂ yields apparently tetra-Et subphosphate and Me₂C:CMe₂.

Zhurnal Obshchei Khimii published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Application In Synthesis of 594-81-0.

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

Pruschinski, Lucas published the artcileSuzuki-Miyaura Cross-Couplings under Acidic Conditions, Application of 2,5-Dibromo-3,4-dinitrothiophene, the publication is Synthesis (2020), 52(6), 882-892, database is CAplus.

Suzuki-Miyaura reactions with Pd(PPh₃)₄ had carried out using lithium N-phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki-Miyaura reaction have been examined

Synthesis 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, Application of 2,5-Dibromo-3,4-dinitrothiophene.

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

Freese, Tyll published the artcileAnionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold, SDS of cas: 52431-30-8, the publication is Tetrahedron (2017), 73(36), 5350-5357, database is CAplus.

The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (x-ray anal.) as well as palladium complexes (x-ray anal.). The ¹³C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142.1 ppm (Molsidomine carbene) and δ = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions.

Tetrahedron 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, SDS of cas: 52431-30-8.

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

Kulhanek, Jiri published the artcile3,4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems, Related Products of bromides-buliding-blocks, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2017), 53(1), 46-53, database is CAplus.

A series of quadrupolar D-π-A-π-D mols. bearing methoxythiophene terminal donor and systematically enlarged/varied π-linkers, e.g., I was synthesized by employing cross-coupling and Knoevenagel reactions. 3,4-Dinitrothiophene was utilized as a central acceptor unit in quadrupolar D-π-A-π-D push-pull-push chromophores. Optical properties were studied by electronic absorption spectra. Fundamental optoelectronic properties were investigated by semiempirical PM7 calculations It was shown that by varying the p-conjugated system the longest wavelength absorption maxima could be shifted from 341 to 489 nm. The calculated HOMO-LUMO gaps were found within the range of 6.69-7.29 eV, while the second-order mol. polarizabilities could be tuned from 0.038 to 1.578 × 10-27 esu.

Chemistry of Heterocyclic Compounds (New York, NY, United States) 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

Wang, Pingyuan published the artcileSynthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators, Application In Synthesis of 401-55-8, the publication is Journal of Medicinal Chemistry (2020), 63(10), 5159-5184, database is CAplus and MEDLINE.

EPAC plays a central role in various biol. functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, the synthesis and biochem. evaluation of a series of non-cyclic nucleotide EPAC1 activators is reported. Several potent EPAC1 binders were identified, e.g., I, which promote EPAC1 GEF activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity towards EPAC over PKA and GPCRs. Moreover, four compounds exhibited improved selectivity towards activation of EPAC1 over EPAC2 in cells. Of these, I was found to robustly inhibit IL-6-activated STAT3 and subsequent induction of the pro-inflammatory VCAM1 cell adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacol. tools for elucidation of EPAC function as well as promising drug leads for the treatment of relevant human diseases.

Journal of Medicinal Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C19H15NO3, Application In Synthesis of 401-55-8.

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

Wang, Bing Hui published the artcileInhibition of eukaryote protein kinases by isoquinoline and oxazine alkaloids, SDS of cas: 518-67-2, the publication is Planta Medica (1997), 63(6), 494-498, database is CAplus and MEDLINE.

The aporphine isoquinoline alkaloid apomorphine is a potent inhibitor of the catalytic subunit (cAK) of rat liver cAMP-dependent protein kinase (PKA), myosin light chain kinase (MLCK), and Ca²⁺– and phospholipid-dependent protein kinase C (PKC) (IC₅₀ values 1, 11, and 8 μM, resp.). However, a number of O-methylated analogs of apomorphine are inactive or poor inhibitors of cAK. The benzophenanthridine isoquinoline alkaloid sanguinarine is a potent inhibitor of cAK but is a relatively poor inhibitor of PKC (IC₅₀ values 6 and 217 μM, resp.). However a number of methylated analogs of sanguinarine are inactive as cAK inhibitors. The aporphine isoquinoline alkaloids (+)-boldine and bulbocapnine are noncompetitive inhibitors of MLCK with respect to both peptide substrate and ATP. The inhibition of cAK, MLCK, and PKC by apomorphine and sanguinarine is competitive with respect to ATP as substrate. The oxazine alkaloids darrow red, nile blue A, and oxazine 170 are variously effective as inhibitors of cAK, MLCK, PKC, and CDPK (IC₅₀ values 4-65 μM). Ca²⁺ binds to apomorphine and (+)-boldine which, together with nile blue A and oxazine 170, are potent inhibitors of calmodulin (CaM)-dependent MLCK (IC₅₀ values 11, 12, 4, and 7 μM, resp.), and interact with dansyl-CaM.

Planta Medica 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 C3H5BN2O2, SDS of cas: 518-67-2.

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

Ding, Hairong published the artcileCompeting hydrogen bonding and halogen bonding interactions in crystal engineering: A case study of bi-functional donor molecules, Synthetic Route of 1998-61-4, the publication is Chemical Physics (2014), 30-37, database is CAplus.

Based on the recent determined co-crystals of a set of bi-functional donor mols. with two isomeric sym. acceptors, the competition between hydrogen bonding and halogen bonding interactions in crystal engineering was studied in this work using the M06-2x and ωB97XD methods. The preference of the occurrence of secondary weak interactions was observed in hydrogen-bonded complexes. Hydrogen bonding interactions are predicted to be much stronger than corresponding halogen bonding interactions. No obvious difference was found between the systems of the two acceptors under study. The model complexes, in which hydrogen bonds and halogen bonds coexist, show additivity. Finally, a comparison between theor. results and exptl. observations was presented, and the implications of the calculations on the supermol. assemblies based on the two interactions were also discussed.

Chemical Physics published new progress about 1998-61-4. 1998-61-4 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzene,Phenol, name is 4-Bromo-2,3,5,6-tetrafluorophenol, and the molecular formula is C6HBrF4O, Synthetic Route of 1998-61-4.

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

Xiao, Yang published the artcileThermally stable red electroluminescent hybrid polymers derived from functionalized silsesquioxane and 4,7-bis(3-ethylhexyl-2-thienyl)-2,1,3-benzothiadiazole, Synthetic Route of 303734-52-3, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (2009), 47(21), 5661-5670, database is CAplus.

Hyperbranched organic-inorganic hybrid conjugated polymers P1 and P2 were prepared via FeCl₃-oxidative polymerization of 4,7-bis(3-ethylhexyl-2-thienyl)-2,1,3-benzothiadiazole (A) and octa(3-ethylhexyl-2-thienyl-phenyl)polyhedral oligomeric silsesquioxane (POSS) (B) at different POSS concentrations Compared to linear polymer PM derived from A, P1, and P2 exhibit much higher PL quantum efficiency (ϕ_PL-f) in condensed state with improved thermal stability. ϕ_PL-f of P1 and P2 increased by 80% and 400%, and the thermal degradation temperatures of P1 and P2 are increased by 35° and 46°, resp. Light-emitting diodes were fabricated using P1, P2, and PM. While the electroluminescent spectra of both P1 and PM show λ_max at 660 nm, P1 exhibits a much narrower EL spectrum and higher electroluminescence (∼500%) compared with PM at a same voltage and film thickness. The maximum current efficiency of P1 is more than seven times of that of PM. The turn-on voltages of the LEDs are in the order of P2>PM>P1. LED prepared by blending P1 with MEH-PPV shows a maximum luminescence of 2.6 × 10³ cd/m² and a current efficiency of 1.40 cd/A, which are more than twice (1.1 × 10³ cd/m²) and five times (0.27 cd/A) of LED of PM/MEH-PPV blend, resp.

Journal of Polymer Science, Part A: Polymer Chemistry published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C14H31NO2, Synthetic Route of 303734-52-3.

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