Month: December 2022

Orda, V. V. published the artcileTransmission of inductive effect of substituents SCF₃, SOCF₃, and SO₂CF₃, through a methylene group, Application of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, the publication is Zhurnal Obshchei Khimii (1965), 35(9), 1628-36, database is CAplus.

cf. CA 63, 1684g. From N.M.R. spectral shifts and pK_a values of substituted toluic, acetic, and phenylacetic acids the following values were deduced for the Taft-Hammett substituents constants: CF₃SCH₂, 0.12 for m- and 0.15 for p-; CF₃SOCH₂, 0.24 for p-; CF₃SO₂CH₂, 0.29 for m- and 0.31 for p-group. The major contribution to these is from the inductive effect but a small and usual negative contribution of the conjugation effect was displayed. The following pK_a values were obtained for: m-CF₃SCH₂C₆H₄CO₂H 5.52, p-isomer 5.48; CF₃SO₂CH₂ m-isomer 5.26, p-isomer 5.23. pK_a values for: CF₃SCH₂CO₂H 2.95; CF₃SOCH₂CO₂H 2.06; CF₃SO₂CH₂CO₂H 1.88. A good agreement was obtained for pK_a of these acids by the rule suggested by Charton (CA 60, 15717h). The pK_a values were calculated from pH data at half neutralization points. ICH₂CO₂Me and CF₃SAg in Me₂CO 6 days gave 70% CF₃SCH₂CO₂Me (I), b. 128°, b₈₀ 71°, n²²_D 1.3896, which with 2N, NaOH at 50° gave the free acid, b₃₁ 101° n²⁰_D 1.3990, d₂₀ 1.4953. PhPCl₂ treated with Cl₂, followed by CF₃SCH₂CO₂H at 70-80°, gave 97% CF₃SCH₂COCl, b. 113-14°; amide m. 89-90°; anilide m. 93-4°. I and 27% H₂O₂ in AcOH refluxed 2 hrs. gave 53% CF₃SOCH₂CO₂Me, b₆ 75-6°, n²⁶_D 1.4089, d₁₆ 1.4877, which with 2N NaOH gave the free acid, m. 78-9.5°. PhCH₂I and CF₃SAg in Me₂CO 4 days gave PhCH₂SCF₃, 66%, b₃₀ 76-7°; similarly were prepared: 68% m-FC₆H₄CH₂SCF₃, b₃₀ 79-80°; p-isomer b₂₆ 78-9°. Oxidation with H₂O₂ gave: 52% PhCH₂SOCF₃, m. 78-9°; 62% m-FC₆H₄CH₂SOCF₃, m. 49-50°; p-isomer, 64%, m. 81-2°. More drastic oxidation with H₂O₂ gave: PhCH₂SO₂CF₃, 74%, m. 103-4°; m-fluoro analog m. 94-5.5°; p-isomer m. 113-14°. Br₂ and p-MeC₆H₄SCF₃ under uv light in C₆H₆ gave 73% p-BrCH₂C₆H₄SCF₃, m. 54-5.5°, b₁₃ 115-18°, which with KCN in aqueous EtOH 1 hr. gave p-NCCH₂C₆H₄SCF₃, m. 22-4°, b₁₃ 135-7°. This heated with aqueous NaOH gave p-CF₃SC₆H₄CH₂CO₂H, m. 116-17.5°, also formed from: p-CF₃SC₆H₄COMe and S in morpholine in 16 hrs. at 160°, followed by treatment with aqueous HCl, to yield the morpholide of above acid, m. 72-3°, which refluxed with 10% NaOH 5 hrs. gave the above free acid. The acid heated with 24% H₂O₂ gave 51% p-CF₃SO₂C₆H₄CH₂CO₂H, m. 124-5°. p-CF₃OC₆H₄CO₂Et reduced with LiAlH₄ at room temperature to 76% p-CF₃OC₆H₄C₂OH, b₁₀ 95-6°, which with saturated HBr 4 hrs. at 80° gave 80% p-CF₃OC₆H₄CH₂Br, b₉ 78-9°, m. 23-4°, which with KCN gave the corresponding nitrile, 63%, b₁₀ 112-13°, which with 20% NaOH gave p-CF₃OC₆H₄CH₂CO₂H, m. 86-7°. The following acids were also reported: m-HO₂CC₆H₄CH₂SCF₃, m. 107-8°; p-isomer m. 159-60°; m-HO₂CC₆H₄CH₂SO₂CF₃, m. 176-7.5°; p-isomer m. 234-5.5°. The following substituent constant values were obtained from pK_a data for: CF₃O group, 0.32-0.4; CF₃S, 0.46-0.49; CF₃SO₂, 0.96-1.04. The NHCOCF₃ group had substituent constant 0.42 for the purely inductive effect from pK_a data and 0.38 from N.M.R. shifts. The conjugation effect contribution is about -0.21.

Zhurnal Obshchei Khimii published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, Application of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane.

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

Fan, Bingbing published the artcileHigh-performance conjugated terpolymer-based organic bulk heterojunction solar cells, SDS of cas: 303734-52-3, the publication is Journal of Materials Chemistry A: Materials for Energy and Sustainability (2016), 4(36), 13930-13937, database is CAplus.

Recently, conjugated terpolymers comprising 3 components have attracted tremendous attention. However, quite a few examples of high-performance terpolymers have been reported. We present 2 terpolymers named PtDDA and PtDAA, in which bithiophene (BT) and benzo[1,2-c:4,5-c’]dithiophene-4,8-dione (T1) were chosen as the donor and acceptor units, resp. Thieno[3,2-b]thiophene (TT) and thiazolo[5,4-d]thiazole (TTz) were used as the third component. It is interesting to find that the PtDDA terpolymer shows a typical D1-D2-D1-A1 structure while PtDAA shows a D1-A1-D1-A2 structure. Without using additives or post-annealing processes, PtDAA-based solar cells show a high PCE of 8.1%, with an unprecedented fill factor (FF) of 0.74, which is much higher than those of PtDDA-based devices (PCE =3.4%, FF =0.55). The high efficiency of 8.1% is one of the highest values reported so far for organic solar cells based on conjugated terpolymers. The high performance is mainly ascribed to the efficient carrier transport in the PtDAA:PC₇₁BM active layer, high crystallinity of PtDAA, and high domain purity. The results suggest that constructing conjugated terpolymers with one donor and two acceptor units is an effective strategy for designing high-performance solar cell materials.

Journal of Materials Chemistry A: Materials for Energy and Sustainability 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 C12H19BrS, SDS of cas: 303734-52-3.

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

Tang, Wei-Ke published the artcileIrradiation-Induced Cobaloxime-Catalyzed C-H Monofluoroalkylation of Styrenes at Room Temperature, Formula: C4H6BrFO2, the publication is Organic Letters (2019), 21(1), 196-200, database is CAplus and MEDLINE.

A cobaloxime-catalyzed photochem. synthesis of allyl monofluorides from styrenes is described herein. This method is characterized by mild reaction conditions, low-cost catalyst, and broad substrate scope. Furthermore, this convenient method will provide a facile synthesis toward novel monofluoroalkylated natural product and pharmaceutical derivatives Mechanistic investigations indicate that a monofluoroalkyl radical is involved in the catalytic cycle.

Organic Letters 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 C10H17N3O2, Formula: C4H6BrFO2.

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

Li, Yao published the artcileSimple non-fullerene electron acceptors with unfused core for organic solar cells, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Chinese Chemical Letters (2019), 30(1), 222-224, database is CAplus.

Two simple electron acceptors based on unfused bithiophene core and 1,1-dicyanomethylene-3-indanone end group were easily prepared via three synthetic steps. These acceptors exhibited broad absorption in the range of 300 nm to 800 nm, aligned energy levels and high crystallinity. When combined with a wide band gap donor polymer in non-fullerene solar cells, an initial power conversion efficiency of 2.4% was achieved. The relatively low efficiencies were due to the large phase separation in blended thin films, which is originated from their high aggregation tendency in thin films. Our results suggest that these electron acceptors with unfused core are promising candidates for com. application of solar cells due to the low cost starting materials and facile synthesis.

Chinese Chemical Letters 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 C12H19BrS, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

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

Xue, Ding published the artcileDiscovery and Lead Optimization of Benzene-1,4-disulfonamides as Oxidative Phosphorylation Inhibitors, Quality Control of 1178100-39-4, the publication is Journal of Medicinal Chemistry (2022), 65(1), 343-368, database is CAplus and MEDLINE.

Inhibition of oxidative phosphorylation (OXPHOS) is a promising therapeutic strategy for select cancers that are dependent on aerobic metabolism Here, we report the discovery, optimization, and structure-activity relationship (SAR) study of a series of novel OXPHOS inhibitors. The hit compound, benzene-1,4-disulfonamide 1 (I), was discovered in a phenotypic screen selective for cytotoxicity in a galactose-containing medium. Our multi-parameter optimization campaign led to the discovery of 65 (DX3-235)(II), showing nanomolar inhibition of complex I function and ATP production in a galactose-containing medium resulting in significant cytotoxicity. Importantly, 64 (DX3-234)(III), a close analog of 65, is well tolerated in mice and shows significant single agent efficacy in a Pan02 syngeneic pancreatic cancer model, suggesting that highly potent and selective OXPHOS inhibitors can be useful for the treatment of pancreatic cancer.

Journal of Medicinal Chemistry published new progress about 1178100-39-4. 1178100-39-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Sulfamide,Amine,Benzene, name is 4-Bromo-N,N-diethyl-3-methylbenzenesulfonamide, and the molecular formula is C9H9BrO2, Quality Control of 1178100-39-4.

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

Deng, Qinfei published the artcilePhotoredox-catalyzed cascade addition/cyclization of N-propargyl aromatic amines: access to 3-difluoroacetylated or 3-fluoroacetylated quinolines, HPLC of Formula: 401-55-8, the publication is Organic Chemistry Frontiers (2018), 5(1), 19-23, database is CAplus.

The 3-difluoroacetylated quinolines I [R = C₆H₅, 4-CH₃CH₂CO(O)C₆H₄, 9H-fluoren-2-yl, thiophen-2-yl, etc.; R¹ = H, 6-F, 7-CH₃, 6-OCF₃, etc.; X = 2-CF₂C(O)OCH₂CH₃] and 3-fluoroacetylated quinolines I [X = 2-CHFC(O)OCH₂CH₃] were synthesized via a visible-light-induced cascade addition/cyclization of N-propargyl aromatic amines R²C₆H₄NHCH₂CCR (R² = H, 3-Me, 4-Cl, etc.) with Et bromodifluoroacetate or Et bromofluoroacetate catalyzed by fac-Ir(ppy)₃ under mild conditions. For the substrates bearing various substituents on the aniline ring and benzene ring, the reaction proceeded smoothly to give the corresponding difluoroacetylated I [X = 2-CF₂C(O)OCH₂CH₃] or fluoroacetylated quinolines I [X = 2-CHFC(O)OCH₂CH₃] in moderate to high yields.

Organic Chemistry Frontiers 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 C4H6BrFO2, HPLC of Formula: 401-55-8.

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

Xu, Zhuo-Wei published the artcileAn efficient method for the N-formylation of amines under catalyst- and additive-free conditions, Category: bromides-buliding-blocks, the publication is Tetrahedron Letters (2019), 60(18), 1254-1258, database is CAplus.

A simple catalyst- and additive-free method for the N-formylation of amines has been developed. The advantages of this protocol include a wide range of functional group tolerance, high efficiency and a lack of required extra promoters under mild conditions. This convenient strategy will provide a facile synthesis towards N-formamide natural products and pharmaceutical derivatives A mechanism that involves difluorocarbene is proposed for this reaction.

Tetrahedron Letters 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 C6H13I, Category: bromides-buliding-blocks.

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

Qu, Yi published the artcileVisible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[c]quinolin-4-ones, HPLC of Formula: 401-55-8, the publication is Journal of Organic Chemistry (2020), 85(8), 5379-5389, database is CAplus and MEDLINE.

Herein, we describe a new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate. These reactions, which proceed via a cascade involving fluoroalkylation, 6-exo-dig and 5-endo-trig cyclizations, H-transfer step, and oxidative dehydrogenation, provide an efficient and general route to a variety of fused monofluorinated cyclopenta[c]quinolin-4-one derivatives

Journal of Organic 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 C4H6BrFO2, HPLC of Formula: 401-55-8.

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

Wang, Guanghui published the artcileDouble N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation, SDS of cas: 401797-04-4, the publication is Journal of the American Chemical Society (2015), 137(25), 8058-8061, database is CAplus and MEDLINE.

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp² C-H borylation reaction. A sym. pyridine-containing tetraaminodiborane(4) compound was readily prepared as the ligand precursor that could be used, in combination with [Ir(OMe)(COD)]₂, to in situ generate a highly active catalyst for a broad range of (hetero)arene substrates including highly electron-rich and/or sterically hindered ones. This work provides the 1st example of a bidentate boryl ligand in supporting homogeneous organometallic catalysis.

Journal of the American Chemical Society published new progress about 401797-04-4. 401797-04-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronate Esters,Boronic acid and ester, name is 2-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C8H11BO2, SDS of cas: 401797-04-4.

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

Wang, Guanghui published the artcileDouble N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation, Synthetic Route of 1075719-78-6, the publication is Journal of the American Chemical Society (2015), 137(25), 8058-8061, database is CAplus and MEDLINE.

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp² C-H borylation reaction. A sym. pyridine-containing tetraaminodiborane(4) compound was readily prepared as the ligand precursor that could be used, in combination with [Ir(OMe)(COD)]₂, to in situ generate a highly active catalyst for a broad range of (hetero)arene substrates including highly electron-rich and/or sterically hindered ones. This work provides the 1st example of a bidentate boryl ligand in supporting homogeneous organometallic catalysis.

Journal of the American Chemical Society published new progress about 1075719-78-6. 1075719-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(3,4-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C3H12Cl2N2, Synthetic Route of 1075719-78-6.

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