Category: 52287-51-1

Wang, Yuzhuo; Wang, Lei; Chen, Mingjie; Tu, Youshao; Liu, Yu; Zhang, Junliang published an article about the compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine( cas:52287-51-1,SMILESS:BrC1=CC=C2OCCOC2=C1 ).Application of 52287-51-1. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:52287-51-1) through the article.

An efficient palladium-catalyzed enantioselective carboamination reaction of N-Boc-O-homoallyl-hydroxylamines and N-Boc-pent-4-enylamines with aryl or alkenyl bromides was developed, delivering various substituted isoxazolidines I [R = H, Me; R1 = Ph, 3-thienyl, 2-naphthyl, etc.] and pyrrolidines II [R1 = 4-PhC6H4, 3,4-MeO2C6H3, 1-naphthyl, etc.; R2 = H, Me; R3 = Boc, Cbz] in good yields with up to 97% ee. The reaction featured mild conditions, general substrate scope and scalability. The obtained products could be transformed into chiral 1,3-aminoalc. derivatives without erosion of chirality. The newly identified Xu-Phos ligand bearing an ortho-OiPr group was responsible for the good yield and high enantioselectivity.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of 1,4-benzodioxan. I. Some halogenated 1,4-benzodioxans and amino and nitro derivatives thereof》. Authors are Heertjes, P. M.; Knape, A. A.; Talsma, H.; Andriesse, P..The article about the compound:6-Bromo-2,3-dihydrobenzo[b][1,4]dioxinecas:52287-51-1,SMILESS:BrC1=CC=C2OCCOC2=C1).Reference of 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine. Through the article, more information about this compound (cas:52287-51-1) is conveyed.

6-Bromo-1,4-benzodioxan (I), b23 153-4°, was obtained in 60% yield by the method of Ghosh (C.A. 10, 455). I (18.35 g.) in 25 ml. H2O treated dropwise at 60° with 5.5 ml. HNO3 (d. 1.52) gave 60% 6-bromo-7-nitro-1,4-benzodioxan (II), m. 171.9-2.1°. 6-Amino-7-nitro-1,4-benzodioxan (III) (5 g.) in 10 ml. concentrated H2SO4 and 25 ml. H2O diazotized at 20° with 1.75 g. NaNO2 in 3 ml. H2O, then refluxed 3 hrs. with 1.6 g. CuSO4, 0.5 g. Cu turnings, 4 g. NaBr.2H2O, 2 ml. concentrated H2SO4, and 25 ml. H2O gave 60% II. II (2.85 g.) treated at 0° with 12 ml. HNO3 and left 2 hrs. at room temperature yielded 3 g. (80%) crude 6-bromo-5(?),7,8(?)-trinitro-1,4-benzodioxan (IV), m. 248.2-8.6° after crystallization from EtOH-HOAc (1:1) and iso-BuOH. II (5 g.) subjected to cathodic reduction yielded 24% 6-amino-7-bromo-1,4-benzodioxan (V) as the HCl salt (1.25 g.). 6-Acetamido-7-bromo-1,4-benzodioxan (VI) (1.02 g., 80%), m. 179.1-9.4°, was prepared from V.HCl by acetylation for 15 min. with NaOAc and Ac2O in a small amount of H2O. 6-Acetamido-1,4-benzodioxan (VIA) (11.2 g.) was brominated to 14 g. (89%) VI. II (10 g.) reduced, extracted, refluxed 15 min. with concentrated HCl and EtOH, diluted, made alk. with NaOH, extracted with C6H6, and HCl, gas passed into the extract precipitated 6.4 g. (70%) V.HCl. 1,4-Benzodioxan (VII) (300 g.) brominated overnight with Br in HOAc yielded 518 g. (80%) 6,7-dibromo-1,4-benzodioxan (VIII), m. 139.6-40.0°. V.HCl (5 g.) diazotized and treated with refluxing Cu2Br2 gave 3.5 g. (63%) crude VIII. The mother liquor after separation of VIII from VII gave 5(?),6,7,8(?)tetrabromo-1,4-benzodioxan (IX), m. 212.8-13.4°. VIII (297 g.) on nitration gave 361 g. (93%) crude 6,7-dibromo-5,8-dinitro-1,4-benzodioxan (X); recrystallized, it m. 318-19°. When 80 g. X was heated with 600 g. SnCl2.2H2O in 600 ml. concentrated HCl and 600 ml. EtOH, a rapid endothermic reaction occurred at 60°, and when the temperature was kept at 60-70° the reaction was complete in 30 min.; working up gave 41.5 g. (84%) 5,8-diamino-1,4-benzodioxan (XI) as the HCl salt; alternatively, the free XI m. 99.1-9.7° was isolated, XI with excess Ac2O gave 64% di-Ac derivative (XII), m. 287-9°; 1 mole Ac2O gave the mono-Ac derivative (XIII), m. 141.2-1.9°. XIII yields azo dyes. VII (76 g.) in 200 ml. HOAc treated with Cl at 10-20° yielded 80.7 g. (71%) 6,7-dichloro-1,4-benzodioxan (XIV), m. 150.6-1.1°. 4,5-Dichloropyrocatechol (7.5 g.) and 75 g. (CH2Br)2 in 50 ml. (CH2OH)2, heated at 140° and treated with anhydrous K2CO3 until the mixture no longer gave a blue color with FeCl3 (3-4 hrs.), afforded 6.8 g. (70%) XIV. Nitration of XIV gave 84% 6,7-dichloro-5,8-dinitro-1,4-benzodioxan (XV), m. 287.78.6°, which, reduced with SnCl2 and HCl in EtOH and acetylated in C6H6 at 50°, gave 5,8-diacetamido-6,7-dichloro-1,4-benzodioxan (XVI), m. 299.0-300.3° (decomposition). Alternatively, HCl was passed into a mixture of 50 g. SnCl2.2H2O in 100 ml. HOAc and heated with 5 g. XV; at 60° reaction set in with a rise in temperature to 90°, and was complete in 1 hr., yielding 5,8-diamino-6,7-dichloro-1,4-benzodioxan (XVII), decompose 137-40°, slowly oxidizes in air. The HCl salt of 6-amino-1,4-benzodioxan (XVIII) (39 g.) in 65 ml. H2O and 65 ml. concentrated HCl diazotized at 0° with 18 g. NaNO2 in 40 ml. H2O and the solution added to 30 g. Cu2Cl2 in 100 ml. concentrated HCl and heated at 70°, gave 26 g. (76%) 6-chloro-1,4-benzodioxan (XIX), b3 98-100°. XIX (5 g.) nitrated with HNO3-H2SO4 at 15° and the product crystallized from Me2CO-HOAc (1:1) gave 4.5 g. (73%) 6-chloro-7-nitro-1,4-benzodioxan (XX), m. 161.7-2.1°, also prepared by diazotization of III and then treatment with Cu2Cl2. VIA (20.4 g.) in 100 ml. HOAc, treated with 1.9 g. Cl in 50 ml. HOAc, the solution added to H2O and the product crystallized from 50% aqueous Me2CO gave 6-acetamido-7-chloro-1,4-benzodioxan (XXI), m. 171.7-2.4°. Hydrogenation of 4 g. XX in EtOH in the presence of Raney Ni at room temperature, filtration, and acidification with HCl gave 4 g. (97%) of the HCl salt of 6-amino-7-chloro-1,4-benzodioxan (XXII); acetylation gave a crude yield of 86% crude XXI, converted into the HCl salt of XXII.HCl by refluxing with 1:1 EtOH-concentrated HCl.

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HPLC of Formula: 52287-51-1. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about Elucidating the Structure-Property Relationships of Donor-π-Acceptor Dyes for Dye-Sensitized Solar Cells (DSSCs) through Rapid Library Synthesis by a One-Pot Procedure. Author is Fuse, Shinichiro; Sugiyama, Sakae; Maitani, Masato M.; Wada, Yuji; Ogomi, Yuhei; Hayase, Shuzi; Katoh, Ryuzi; Kaiho, Tatsuo; Takahashi, Takashi.

The preparation of organic dyes with excellent high power conversion efficiency is important for the further improvement of dye-sensitized solar cells. We describe the rapid synthesis of a 112-membered donor-π-acceptor dye library by a one-pot procedure, evaluation of power conversion efficiencies, and elucidation of structure-property relationships. No obvious correlations between molar absorption coefficient and the η were observed, whereas the HOMO and LUMO levels of the dyes were critical for η. The dyes with a more pos. EHOMO, and with an ELUMO < -0.80 V, exerted higher power conversion efficiencies. The proper driving forces were crucial for a high short-circuit c.d., and it was the most important parameter for a high η. The above criteria of EHOMO and ELUMO should be useful for creating high power conversion efficiency dyes; nevertheless, that was not sufficient for identifying the best combination of donor, π, and acceptor blocks. Combinatorial synthesis and evaluation was important for identifying the best dye. Compound(52287-51-1)HPLC of Formula: 52287-51-1 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine), if you are interested, you can check out my other related articles.

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SDS of cas: 52287-51-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability. Author is Chen, Yi-Hung; Ellwart, Mario; Toupalas, Georgios; Ebe, Yusuke; Knochel, Paul.

The treatment of various N-morpholino amides with TMPZnCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)2 in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t1/2 in air: 1-3 h) after solvent evaporation These enolates undergo Pd- and Cu-catalyzed cross-couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl3·2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23 % overall yield.

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Pyrazole – Wikipedia,
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Recommanded Product: 52287-51-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C-N cross-coupling reaction of trans-4-hydroxy-L-proline with aryl halides. Author is Reddy, V. Prakash; Kumar, A. Vijay; Rao, K. Rama.

Trans-4-Hydroxy-L-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs2CO3 as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-L-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields.

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Pyrazole – Wikipedia,
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Recommanded Product: 52287-51-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis. Author is Liu, Dong; Liu, Zhao-Ran; Ma, Cong; Jiao, Ke-Jin; Sun, Bing; Wei, Lei; Lefranc, Julien; Herbert, Simon; Mei, Tian-Sheng.

A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochem. (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C-N bond from the resulting NiIII species at room temperature

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Novel ATP-Competitive Kinesin Spindle Protein Inhibitors, published in 2007-10-04, which mentions a compound: 52287-51-1, mainly applied to biphenyl sulfonamide antitumor kinesin spindle protein inhibitor SAR, Computed Properties of C8H7BrO2.

Kinesin spindle protein (KSP), an ATPase responsible for spindle pole separation during mitosis that is present only in proliferating cells, has become a novel and attractive anticancer target with potential for reduced side effects compared to currently available therapies. We report herein the discovery of the first known ATP-competitive inhibitors of KSP, which display a unique activity profile as compared to the known loop 5 (L5) allosteric KSP inhibitors that are currently under clin. evaluation. Optimization of this series led to the identification of biphenyl sulfamide 20 (I), a potent KSP inhibitor with in vitro antiproliferative activity against human cells with either wild-type KSP (HCT116) or mutant KSP (HCT116 D130V). In a murine xenograft model with HCT116 D130V tumors, 20 showed significant antitumor activity following i.p. dosing, providing in vivo proof-of-principle of the efficacy of an ATP-competitive KSP inhibitor vs. tumors that are resistant to the other known KSP inhibitors.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 52287-51-1, is researched, SMILESS is BrC1=CC=C2OCCOC2=C1, Molecular C8H7BrO2Journal, Tetrahedron Letters called Synthesis of new chiral diphosphine ligand (BisbenzodioxanPhos) and its application in asymmetric catalytic hydrogenation, Author is Pai, Cheng-Chao; Li, Yue-Ming; Zhou, Zhong-Yuan; Chan, Albert S. C., the main research direction is diphosphine chiral ligand preparation structure ligand ruthenium hydrogenation catalyst; crystal structure bis ethylenedioxybiphenyldiyl bisdiphenylphosphine chiral ligand; mol structure bis ethylenedioxybiphenyldiyl bisdiphenylphosphine chiral ligand.Related Products of 52287-51-1.

The new chiral diphosphine ligand [(5,6),(5′,6′)-bis(1,2-ethylenedioxy)biphenyl-2,2′-diyl]bis(diphenylphosphine) (I; BisbenzodioxanPhos) was successfully prepared and used in Ru-catalyzed asym. hydrogenation of 2-(6′-methoxy-2′-naphthyl)propenoic acid and β-keto esters with high enantioselectivity (92.2% and up to 99.5% ee, resp.).

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HPLC of Formula: 52287-51-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about Benzyloxycalix[8]arene supported Pd-NHC cinnamyl complexes for Buchwald-Hartwig C-N cross-couplings. Author is Abi Fayssal, Sandra; Naret, Timothee; Huc, Vincent; Buendia, Julien; Martini, Cyril; Schulz, Emmanuelle.

The scalable synthesis of Pd-NHC cinnamyl complexes supported on benzyloxycalix[8]arene is reported. These catalysts are very active for Buchwald-Hartwig cross-coupling reactions, allowing the coupling of aryl chlorides and bromides with a wide variety of alkyl and aryl amines using low catalytic loadings. The supported complexes also successfully afforded attractive unsym. triarylamines, and in one case, promoted the synthesis of an unprecedented Pd-catalyzed C-H activation product. Thanks to the calixarenic support, the target products could be isolated with low levels of residual palladium, and in some cases, even below the restrictive toxic metal standards applied by the pharmaceutical industry. Through an easy to implement procedure, these perfectly characterized catalysts thus combine the best of homogeneous and heterogeneous catalysis: high efficiency (similar to or even better than the corresponding homogeneous complexes) and low Pd leaching levels expected from heterogeneous catalysts.

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Recommanded Product: 52287-51-1. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine, is researched, Molecular C8H7BrO2, CAS is 52287-51-1, about An efficient method for the preparation of tertiary esters by palladium-catalyzed alkoxycarbonylation of aryl bromides.

The palladium-catalyzed alkoxycarbonylation of aryl bromides is described for the efficient preparation of tertiary esters. The protocol proved compatible with a wide variety of functionalized (hetero)aromatic bromides, as well as several different sterically hindered tertiary alcs., affording the alkoxycarbonylated products in high yields. Finally, the formation of aromatic trityl esters is discussed.

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