Month: November 2022

Wang, Haihua published the artcileConcurrent alkylation and crosslinking of polyaniline for enhanced anticorrosive performance of waterborne alkyd coating, Application In Synthesis of 143-15-7, the publication is Progress in Organic Coatings (2022), 106865, database is CAplus.

The uniform dispersion and long-term stability of hydrophobic polyaniline (PANI) in waterborne polymer matrix always remains a challenge. Here, PANI was chem. modified by 1,12-dibromododecane to prepare functionalized PANI (PANI-12Br(II)), and simultaneously achieve N-alkylation and chem. crosslinking of PANI chains. In addition, 1-bromododecane was utilized to modify PANI to prepare PANI-12Br(I) as a control. The degree of alkylation of PANI-12Br(II) was higher than that of PANI-12Br(I), as well as the content of N⁺ species in PANI-12Br(II). Also, the interaction between the PANI-12Br(II) chains decreased. The colloidal particle size decreased from 703.9 nm to 297.3 nm, and the dispersibility and long-term colloidal stability of PANI-12Br(II) in aqueous system were significantly improved. The water adsorption of as-prepared PANI-12Br(II)/WAR nanocomposite decreased from 18.37% to 4.27%, and the contact angle increased from 63.4° to 112.5°. Compared with WAR and PANI/WAR-0.5%, the coating resistance of PANI-12Br(II)/WAR-0.5% increased by 5 and 4 orders of magnitude, and the corrosion c.d. decreased by 3 and 2 orders of magnitude. The PANI-12Br(II)/WAR-0.5% displayed better long-term anticorrosive performance than PANI-12Br(I)/WAR-0.5%. The anticorrosive mechanisms were also put forward. The PANI-12Br(II) can be applied as a promising class of corrosion inhibitors in waterborne polymer matrixes.

Progress in Organic Coatings published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C3H5BN2O2, Application In Synthesis of 143-15-7.

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

Herron, Alastair N. published the artcileδ-C-H Halogenation Reactions Enabled by a Nitrogen-Centered Radical Precursor, Application of 1-Bromooctane, the publication is Organic Letters (2022), 24(20), 3652-3656, database is CAplus and MEDLINE.

Herein, new hydrazonyl carboxylic acids RN(S(O)₂R¹)N=C(Me)C(O)OH (R = octyl, 2-(adamantan-1-yl)ethyl, 4-methylpentyl, etc.; R¹ = 4-methylphenyl, 4-methoxyphenyl, 4-bromophenyl, 4-(trifluoromethyl)phenyl) precursor to nitrogen-centered radicals and its application toward remote C-H fluorination and chlorination reactions of sulfonyl-protected alkyl amines R¹S(O)₂NHR² (R² = 4-fluorooctyl, 2-(2-fluorocyclobutyl)ethyl, 4-fluoro-4-methylpentyl, etc.) via 1,5-HAT were disclosed.

Organic Letters published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Application of 1-Bromooctane.

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

Lin, Tzu-Chau published the artcileSynthesis and two-photon properties of a multipolar chromophore containing indenofluorenyl units, COA of Formula: C10H16Br3N, the publication is Tetrahedron Letters (2009), 50(2), 182-185, database is CAplus.

A new multipolar fluorophore derived from triphenylamine as the core with diphenylaminoindenofluorenyl moieties incorporated at the peripheral positions has been synthesized and exptl. shown to possess strong two-photon absorptivities in near-IR region and intense upconverted visible emission under the irradiation of femtosecond laser pulses.

Tetrahedron Letters 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, COA of Formula: C10H16Br3N.

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

Chen, Chiu-Hsiang published the artcileSynthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends, Application In Synthesis of 52431-30-8, the publication is Macromolecules (Washington, DC, United States) (2010), 43(2), 697-708, database is CAplus.

Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)_m-(thiophene acceptor)_n, were rationally designed and successfully synthesized by the palladium-catalyzed Stille coupling. The 4H-cyclopenta[2,1-b:3,4-b’]dithiophene (CPDT) unit serves as the donor for P1-P4, while the benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, resp. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3,2-b:2′,3′-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BT > QU presumably due to the quinoid form population in the polymers, the optical band gaps can be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, resp. It is found that the two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects on the P1 and P5 as well as P2 and P6, resp., leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC₇₁BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b’]dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows a higher band gap with strong absorption in visible region, while PCPDTBT has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P1/PC₇₁BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC₇₁BM (PCE = 1.4%) or P1/PC₇₁BM (PCE = 2.0%) under the identical conditions. Such an improvement is ascribed to the complementary absorption and compatible structure of P1 and PCPDTBT polymers.

Macromolecules (Washington, DC, 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, Application In Synthesis of 52431-30-8.

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

Kaplan, Justin M. published the artcileScalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones, SDS of cas: 76283-09-5, the publication is Organometallics (2019), 38(1), 85-96, database is CAplus.

The Pd-catalyzed carbonylation of cyclic β-chloro enones using simple phosphine ligands is described. Screening identified P(Me)(t-Bu)₂ as the most general ligand for an array of chloro enone electrophiles. The reaction scope was evaluated on a milligram scale across 80 examples, with excellent reactivity observed in nearly every case. Carbonylation can be achieved even in the presence of potentially sensitive or inhibitory functional groups, including basic nitrogens as well as aryl chlorides or bromides. Twenty examples were run on a gram scale, demonstrating scalability and practical utility. Using P(Me)(t-Bu)₂, the reaction rate depends on both nucleophile and electrophile identity, with completion times varying between 3 and >18 h under a standard set of conditions. Switching to P(t-Bu)₃ for the carbonylation of 3-chlorocyclohex-2-enone with MeOH results in a dramatic rate increase, enabling effective catalysis with kinetics consistent with rate-limiting mass transfer. Stoichiometric oxidative addition of 3-chlorocyclohex-2-enone and 3-oxocyclohex-1-enecarbonyl chloride to both Pd[P(t-Bu)₃]₂ and Pd(PCy₃)₂ has enabled characterization and isolation of several potential catalytic intermediates, including Pd-vinyl and Pd-acyl species supported by P(t-Bu)₃ and PCy₃ ligands. Monitoring the oxidative addition of 3-chlorocyclohex-2-enone to Pd(PCy₃)₂ by NMR spectroscopy indicates that coordination of the alkene precedes oxidative addition As a result of these studies, Me 3-oxocyclohex-1-enecarboxylate was synthesized via Pd-catalyzed carbonylation of 3-chlorocyclohex-2-enone in 90% yield on a 60 g scale with only 0.5 mol % catalyst loading.

Organometallics 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, SDS of cas: 76283-09-5.

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

Matsuzawa, Tsubasa published the artcileTransition-Metal-Free Synthesis of N-Arylphenothiazines through an N- and S-Arylation Sequence, Computed Properties of 89694-44-0, the publication is Organic Letters (2021), 23(6), 2347-2352, database is CAplus and MEDLINE.

An efficient synthetic method of N-arylphenothiazines, e.g., I, from o-sulfanylanilines under transition-metal-free conditions is disclosed. An N- and S-arylation sequence of o-sulfanylanilines enabled the authors to synthesize a wide variety of N-arylphenothiazines. In particular, one-pot synthesis of N-arylphenothiazines was accomplished from easily available modules through preparation of o-sulfanylanilines by thioamination of aryne intermediates and following N- and S-arylation sequence.

Organic Letters 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, Computed Properties of 89694-44-0.

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

Yoshida, Tatsuki published the artcileN-Methylphenothiazine S-Oxide Enabled Oxidative C(sp²)-C(sp²) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums, Quality Control of 849062-12-0, the publication is Organic Letters (2021), 23(24), 9664-9668, database is CAplus and MEDLINE.

The development of a transition-metal-free oxidative C(sp²)-C(sp²) coupling of readily available boronic acids RB(OH)₂ (R = Ph, 2-naphthyl, 1-hexenyl, 2-(4-bromophenyl)vinyl, etc.) and organolithiums R¹Li (R¹ = 4-bromophenyl, vinyl, 2-naphthyl, etc.) via phenothiazinium ions I was reported. Various biaryl, styrene, and diene derivatives RR¹ were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions I. The mechanism of phenothiazinium formation using PTZSO was investigated using theor. calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Organic Letters published new progress about 849062-12-0. 849062-12-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Bromo-5-methoxyphenyl)boronic acid, and the molecular formula is C4H4N2O2, Quality Control of 849062-12-0.

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

Fox, Martin E. published the artcileN-Alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 7. Hydroxylamine-alkyne cyclizations. Formation of cyclic nitrones and application to the synthesis of the proposed structure for (±)-acacialactam, Application of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1994), 3379-95, database is CAplus.

The cyclization of alkynylhydroxylamines to give five-, six- and seven-membered cyclic nitrones is described. A concerted intramol. ene-like pathway is proposed for the addition of the N-O-H group across the triple bond. Using 3,7-dimethyl-3,4,5,6-tetrahydro-2H-azepine 1-oxide as the starting material, the seven-membered lactam structure proposed for the natural product acacialactam was prepared and was found to be incorrect. (E)-CH₂:CHCMe(OH)CH₂CH₂CH:CMeCONH₂ is proposed as the structure for acacialactam.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Application of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Tirpak, Michael R. published the artcileReaction of dicobalt octacarbonyl with some acetylenic compounds, COA of Formula: C7H11Br, the publication is Journal of Organic Chemistry (1960), 687-90, database is CAplus.

In a recent investigation (CA 50, 12809i), it was reported that Co₂(CO)₈ reacted with RCCR’ (I) according to the reaction: I + Co₂(CO)₈ → RC₂R’Co₂(CO)₆ + 2CO. In the present study the effect of various groups (R and R’) upon the rate of reaction was determined The relative reactivities of various I were determined from the half-lives of their reactions. The half-lives were obtained from a plot of volume of evolved CO vs. time. The half-life of the reaction with BuCCH (II) was assigned a value of 100 on the relative reactivity scale and the relative reactivity of each of the I was calculated from: relative reactivity = t_1/2 II/t_1/2 I × 100. The average half-life for II was found to be 320 sec. The differences in the relative reactivities were not great; however, CO₂H, CO₂Me, and CH₂OH groups appeared to enhance the reactivity when attached to the triple bonded C. An anomalous behavior of certain propargyl-type halides was found and was attributed to a possible coupling reaction of these halides in the presence of Co₂(CO)₈. The following I (general methods of their preparation were given) were prepared and their relative reactivities determined (R, R’, b.p./mm., n_D/temperature, d₄/temperature, relative reactivity given): Bu, H, 70.5°/atm., 1.3970/24°, 0.7137/26°, 100; Bu, D, 70-4°/atm., 1.3970/23°, 0.722/22°, 105; Pr, Me, 82-8°/760, 1.4127/24°, 0.7401/20°, 60; Et, Et, 79-80°/760, 1.4101/23°, 0.7231/20°, 98; tert-Bu, H, 35-6°/760, 1.3743/21°, 0.6683/20°, 88; Me, Me, 29°/760, 1.3880/27°, 0.6913/20°, 56; CH₂:CMe, H, 32.5°/760, 1.4148/21°, 0.695/25°, 119; HCC(CH₂)₄, H, 32.5-3.5°/55, 1.4454/21°, 0.8195/24°, 81; Ph, H, 44-5°/22, 1.5488/22°, 0.9283/22°, 114; o-tolyl, H, 42-4°/6, 1.5460/21°, 0.9224/24°, 78; m-tolyl, H, 62-4°/18, 1.5427/21°, 0.9073/26°, 110; p-tolyl, H, 61-2°/20, 1.5455/24°, 0.9159/20°, 112; 2,4-Me₂C₆H₃, H, 69-71°/9, 1.5451/25°, 0.930/23°, 88; 2,5-Me₂C₆H₃, H, 49°/2, 1.5412/24°, 0.9180/21°, 88; 3,4-Me₂C₆H₃, H, 59-62°/3, 1.5494/25°, 0.9246/24°, 115; 2,4,6-Me₃C₆H₂, H, 62-3°/2.5, 1.5440/25°, 0.9185/25°, 20; 2,6,4-Me₂(tert-Bu)C₆H₂, H, 88-90°/2, 1.5313/23°, 0.9018/22°, 23; Ph, Ph, 150°/8 (m. 58-60°), -, -, 60; Bu, CO₂H, 116°/7, 1.4607/23, 0.9775/23°, 160; Et, (CH₂)₃CO₂H, 126-7°/8, 1.4543/28° 0.9762/28°, 60; Ph, CO₂H, -(m. 135-7°), -, -, 226; H, CH₂OH, 111-12°/atm., 1.4312/22°, 0.9338/24°, 194; H, CMe₂OH, 103°/atm., 1.4204/24°, 0.8518/28°, 177; Bu, CH₂OH, 77-8°/4, 1.4520/30°, 0.8810/28°, 120; Bu, CHMeOH, 67-9°/8, 1.4468/23°, 0.8747/24°, 123; tert-Bu, CH₂OH, 68-9°/17, 1.4421/24°, 0.8600/23°, 89; Am, CO₂Me, 96°/12, 1.4460/23, 0.9260/22, 152; Et, (CH₂)₃CO₂Me, 85-6°/9, 1.4447/21°, 0.9365/21°, 68; Me, (CH₂)₄CO₂Me, 94°/13, 1.4470/22°, 0.9552/23°, 55; H, (CH₂)₅CO₂Me, 85-6°/10, 1.4403/23°, 0.9428/24°, 92; H, OBu, 40-1°/65, 1.4000/29°, 0.8161/29°, 1; H, CH₂OMe, 60.0-60.5°/760, 1.3948/23°, 0.8410/23°, 177; H, CH₂OCPh₃, -(m. 110.5-11.0°), -, -, 186; H, 2-tetrahydropyranyloxymethyl, 57.5-8.0°/7, 1.4573/21°, 1.0148/21°, 201; H, (CH₂)₅Br, 76.5-7.0°/18, 1.4773/22°, 1.2342/22°, 87; H, (CH₂)₄I, 62-3°/8, 1.5260/28°, 1.5822/26°, 86; H, C₆H₄F-p, -(m. 25-7°), -, -, 92; H, C₆H₄Cl-p, -(m. 43.0-4.5°), -, -, 90; H, C₆H₄Cl-m, 58-60°/9, 1.5630/23°, 1.116/25°, 102; H, C₆H₄Cl-o, 65-6°/12, 1.5694/25°, 1.1249/25°, 102; H, C₆H₄Br-p, -(m. 64.5-6.0°), -, -, 100; H, CH₂Cl, 55.5°/760, 1.4335/22°, 1.0385/23°, 172; H, CH₂Br, 82°/760, 1.4928/22°, 1.5775/22°, 385; H, CMe₂Cl, 74°/760, 1.4160/25°, 0.9085/25°, 178; Bu, CH₂Cl, 56-7°/10, 1.4585/25°, 0.9470/25°, 91; Bu, CH₂Br, 64-5°/8, 1.4910/22°, 1.2427/22°, 315; Bu, CH₂I, 78-9°/7, 1.5387/25°, 1.4914/23°, 476; BrCH₂, CH₂Br, 81-2°/7, 1.5844/30°, 2.0237/29°, 325.

Journal of Organic Chemistry published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C9H11BO3, COA of Formula: C7H11Br.

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

Malamas, Michael S. published the artcileNovel Spirosuccinimide Aldose Reductase Inhibitors Derived from Isoquinoline-1,3-diones: 2-[(4-Bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(11H),3′-pyrrolidine]-1,2′,3,5′(2H)-tetrone and Congeners. 1, Computed Properties of 147181-08-6, the publication is Journal of Medicinal Chemistry (1994), 37(13), 2043-58, database is CAplus and MEDLINE.

Spiro[isoquinolinepyrrolidine]tetrones I [R¹ = H, Cl, F, Br, OMe, CF₃, Me, NO₂; R² = (un)substituted benzyl, benzothiazolylmethyl, alkyl] were prepared and evaluated in vitro for their ability to inhibit glyceraldehyde reduction, using a partially purified bovine lens aldose reductase preparation, and in vivo for their ability to inhibit galactitol accumulation in the lens and sciatic nerve of galactose-fed rats. Substitution at the N-2 position of I with diverse structural substituents (i.e., aralkyl, benzothiazolylmethyl, methyl) produced several excellent series of aldose reductase inhibitors. Optimization of these new series of spirosuccinimides through structure-activity relationship (SAR) studies, including analogy from other drug series (ponalrestat, zopolrestat), led to the design of the clin. candidate I [R¹ = 6-F, R² = 2,4-F(Br)C₆H₃, II]. II exhibited exceptional oral potency in two animal models of diabetic complications, the 14-day galactose-fed and streptozocin-induced diabetic rats, with ED₅₀ values for the sciatic nerve of 0.1 and 0.09 mg/kg/day, resp. Both enantiomeric forms of II exhibited similar inhibitory activity in both in vitro and in vivo assays possibly due to their rapid interconversion. In an ex vivo experiment, the pharmacodynamic effect of II in the plasma of rats and dogs, after a single dose, appeared to be comparable to that of tolrestat.

Journal of Medicinal Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, Computed Properties of 147181-08-6.

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