Month: December 2022

Pilat, S. published the artcileFormation of cyclopentylalkanesulfonates, Product Details of C7H13Br, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1939), 1527-31, database is CAplus.

The Na naphthenesulfonates obtained from natural naphthenic acids through the naphthenyl alcs. and chlorides (C. A. 32, 8753.5) are characterized by their excellent foaming and wetting properties in aqueous solution For comparison with these substances, whose structure has not been fully cleared up, P. and T. undertook the preparation of some cyclic sulfonates (chiefly cyclopentane derivatives, since the naphthenic acids in petroleums are for the most part derived from cyclopentane) in which the sulfonic acid is in primary combination, i. e., as CH₂SO₃H. The starting point for the preparation of sulfonates with a straight alkyl chain, C₅H₉(CH₂)_nSO₃Na (n = 2, 4 or 7) was cyclopentanol, which was converted with boiling concentrated HCl and CaCl₂ into the chloride (87% yield); this through the Grignard reagent with HCHO gave the carbinol, C₅H₉CH₂OH, which, in turn, was converted into the chloride. 2-Cyclopentylethanol (I) and 4-cyclopentylbutanol (II), as also 2-menthylethanol (III), were prepared by the Grignard method for introducing CH₂.CH₂ chains: RMgBr + CH₂.CH₂.O → RCH₂CH₂OMgBr. Chains of 3 CH₂ groups were introduced by treating Grignard compounds with p-MeC₆H₄SO₃(CH₂)₃Cl (IV) or with trimethylene oxide; in this way (7-chloroheptyl)cyclopentane (V) was prepared from C₅H₉(CH₂)₄Br and II from C₅H₉CH₂Cl. For the preparation of sulfonates with a branched chain fenchone was used, which was converted by KOH at 240° into fencholic acid (VI). Reduction of the Et ester of VI gave fencholyl alc. (VII), converted with PCl₅ into the chloride, which with Na₂SO₃ gave 50% Na fencholylsulfonate and, through fencholylmalonic acid, yielded fencholylacetic acid (VIII). Reduction of the Et ester of VIII, conversion of the 2-fencholylethanol (IX) into the chloride and subsequent Strecker reaction yielded Na fencholylethanesulfonate (50% yield), very hygroscopic. Investigation of aqueous solutions of the Na salts so obtained, which will be described in detail later, showed, among other things, that sulfonates in which a cyclopentane ring carries small alkyl groups are characterized by an especially high degree of surface activity and in this respect surpass both cyclopentanes with a long side chain and alkylated cyclohexanes. I, b₁₁ 85°, was obtained in 45% yield by a modification of the Yohe and Adams method (C. A. 22, 2148). Chloride (71% from I and 1.1 mols. PCl₅ refluxed 2 h. in petr. ether), b₆₀ 85-6°, d₄²⁰ 0.955, n_D²⁰ 1.4527; 26.5 g. heated 8 h. at 200° with 80 g. crystallized Na₂SO₃ in an autoclave, with stirring, gave 39 g. (97.5%) Na 2-cyclopentylethanesulfonate, silvery non-hygroscopic needles. (2-Bromoethyl)cyclopentane (71.2% from I heated 2.5 h. with HBr-concentrated H₂SO₄), b₁₉ 77°, d₄²⁰ 1.290, n_D²⁰ 1.4865; its Grignard reagent with ethylene oxide gave 68% II, b₂ 87-92°, n_D²⁰ 1.4610, d₄²⁰ 0.903 (from C₅H₉CH₂Cl and trimethylene oxide the yield was only 5%). (4-Bromobutyl)cyclopentane (90% from II with HBr-H₂SO₄), b₁₇ 110-11°, n_D²⁰ 1.4820, d₄²⁰ 1.187, gives with Na₂SO₃ after 8 h. at 160° in a rotating autoclave Na 4-cyclopentylbutanesulfonate. V (10% from C₅H₉(CH₂)₄Br and IV), b. 120-5°; Na 7-cyclopentylheptanesulfonate, strongly hygroscopic. Menthyl bromide (80% from menthol and HBr-H₂SO₄), b₁₃ 105.5°, d₄²⁰ 1.162, n_D²⁰ 1.4852. III (20%), b₁₀ 132-6°; chloride (35%), b₁₀ 120-5°; Na 2-menthylethanesulfonate. VII (84.5%), b₁₀ 96.5°, [α]_D 8.6°; chloride, b₉ 84°, d₄^21.5 0.949, n_D¹⁷ 1.4702. VIII (46%), b₁₀ 165-6°; Et ester, b₁₀ 146-8°. IX (5% from the Grignard compound of fencholyl chloride with ethylene oxide, or 76% by reduction of the Et ester of VIII with Na in absolute alc.), b₁₀ 134-5°, n_D¹⁸ 1.4761; chloride (65%), b₁₀ 120-6°.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 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, Product Details of C7H13Br.

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

Vetter, Walter published the artcileIdentification and quantification of new polybrominated di-methoxybiphenyls (PBDMBS) in marine mammals from Australia, Recommanded Product: Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, the publication is Organohalogen Compounds (2008), 2388-2391, database is CAplus.

This study aims to verify the hypothesis by the photolytical debromination as well as synthesis of dibromo and tribromo congeners related to 2,2′-diMeO-BB 80, followed by the screening of these products in environmental samples. Using the authentic standard of 2,2′-diMeO-BB 80, it was for the first time possible to quantify residues of 2,2′-diMeO-BB 80 in blubber of dolphins and cetaceans from Australia. Moreover, the calibrated solution of lower BDMBs offered the opportunity to determine these debromination products of 2,2′-diMeO-BB 80 as well. The concentrations of the 2,2′-diMeO-BB 80 related BDMBs were 0.43-1.5% of 2,2′-diMeO-BB 80.

Organohalogen Compounds 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 C10H10O6, Recommanded Product: Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide.

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

Doig, Adrian I. published the artcileSynthesis, Catalytic GPx-like Activity, and SET Reactions of Conformationally Constrained 2,7-Dialkoxy-Substituted Naphthalene-1,8-peri-diselenides, Product Details of C12H25Br, the publication is ACS Omega (2022), 7(31), 27312-27323, database is CAplus and MEDLINE.

Several 2,7-dialkoxy-substituted naphthalene-1,8-peri-diselenides were prepared and tested for catalytic antioxidant activity in NMR-based assay employing the reduction of hydrogen peroxide with stoichiometric amounts of benzyl thiol. Acidic conditions enhanced their catalytic activity, whereas basic conditions suppressed it. The highest activity was observed with 2,7-bis(triethyleneglycol) derivative These compounds serve as mimetics of the antioxidant selenoenzyme glutathione peroxidase. Studies based on NMR peak-broadening effects and EPR spectroscopy indicated that a thiol-dependent SET reaction occurs under the conditions of assay, which can be reversed by the addition of triethylamine. In contrast, peak broadening induced by proton-catalyzed electron transfer during the treatment of naphthalene-1,8-peri-diselenides with trifluoroacetic acid can be suppressed by the addition of excess thiol. These observations provide new insights into the redox mechanisms of these processes.

ACS Omega 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 C12H25Br, Product Details of C12H25Br.

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

Goto, Shunsuke published the artcileThe Process Development of a Novel Aldose Reductase Inhibitor, FK366. Part 1. Improvement of Discovery Process and New Syntheses of 1-Substituted Quinazolinediones, Quality Control of 76283-09-5, the publication is Organic Process Research & Development (2003), 7(5), 700-706, database is CAplus.

The novel aldose reductase inhibitor FK366 I is prepared on multikilogram scale by an improved, practical and cost-effective process. Addition of base to a solution of 2-amino-4-chlorobenzoic acid followed by addition of sodium cyanate at pH 6-7 and a second treatment with aqueous sodium hydroxide yields the quinazoline II; the pH is carefully controlled in the cyanate addition step by addition of hydrochloric acid to the reaction mixture, preventing the decomposition of cyanate while allowing the cyclocondensation reaction to occur at a reasonable rate. Silylation of II with bis(trimethylsilyl)amide in the presence of sulfuric acid (with careful mixing of bis(trimethylsilyl)amide and sulfuric acid to avoid violent reaction) yields an intermediate bis(trimethylsilyloxy)quinazoline which undergoes regioselective alkylation in Et acetate to provide the intermediate III in good yield as a single regioisomer. Alkylation of the remaining free nitrogen of the quinazoline with 4-bromo-2-fluorobenzyl bromide followed by basic hydrolysis of the ethoxycarbonyl moiety yields I on 35 kg scale. The dibenzylated quinazoline IV, resulting from incomplete reaction of II in the regioselective alkylation reaction with Et bromoacetate followed by subsequent dibenzylation, acts as a initiator for the formation of an undesired polymorph of I which is difficult to filter and which forms thick slurries. Seeding solutions of I containing ≥1% of IV with either polymorph of I results in crystallization of the undesired polymorph of I from solution Solutions with 0.5% IV yield different polymorphs depending on the identity of the seed crystal; seeding the solution with a crystal of the undesired polymorph of I provides crystals of the undesired polymorph of I, while seeding the solution with a crystal of the desired polymorph of I results in crystallization of the desired polymorph of I. Monitoring of the initial silylation and regioselective alkylation step by HPLC is used to minimize the amount of IV present in the final product and thus to provide the desired polymorph of I upon recrystallization

Organic Process Research & Development 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, Quality Control of 76283-09-5.

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

Mikroyannidis, J. A. published the artcileSynthesis and application of low band gap conjugated small molecules containing benzobisthiadiazole and thienothiadiazole central units for bulk heterojunction solar cells, Category: bromides-buliding-blocks, the publication is Journal of Materials Chemistry (2011), 21(12), 4679-4688, database is CAplus.

Two conjugated low band gap small mols. (SMs), M1 and M2, containing benzobisthiadiazole and thienothiadiazole central units, resp., were synthesized. Both SMs carried terminal cyanovinylene 4-nitrophenyl at both sides which were connected to the central unit with a thiophene ring. The long-wavelength absorption band was located at 591-643 nm and the optical band gap was 1.62-1.63 eV, which is lower than that of P3HT. These two SMs were studied as electron donor materials along with PCBM or F as electron acceptors for fabrication of bulk heterojunction (BHJ) organic photovoltaic devices. F is a modified PCBM which was previously synthesized and used as an electron acceptor for poly(3-hexylthiophene) (P3HT). The power conversion efficiency (PCE) for M1:PCBM, M1:F, M2:PCBM and M2:F was 1.05%, 2.02%, 1.23% and 2.72%, resp. The higher PCE for the devices with M2 as the electron donor was related to the improved hole mobility for M2. The improved PCE for the devices with F as the electron acceptor was attributed to the more intense absorption of F in the visible region than that of PCBM and also to the higher open circuit voltage resulting from the higher LUMO level of F. the authors have also fabricated devices with M2:F cast film from mixed solvents. The PCE for the BHJ devices with the as cast and thermally annealed M2:F (mixed solvents) is 3.34% and 3.65%, resp.

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, Category: bromides-buliding-blocks.

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

Mikroyannidis, J. A. published the artcileEfficient bulk heterojunction solar cells using an alternating phenylenevinylene copolymer with dithenyl(thienothiadiazole) segments as donor and PCBM or modified PCBM as acceptor, Formula: C4Br2N2O4S, the publication is Solar Energy Materials & Solar Cells (2011), 95(11), 3025-3035, database is CAplus.

A novel low band gap alternating phenylenevinylene copolymer, P, with dithenyl (thienothiadiazole) segments was synthesized by Heck coupling. It was soluble in common organic solvents, showed broad absorption curve with long-wavelength absorption maximum at 580-598 nm and optical band gap of 1.74 eV, which is comparable with the electrochem. band gap of about 1.80 eV. P (electron donor) was blended with PCBM or modified PCBM i.e. F (electron acceptor) to fabricate bulk heterojunction (BHJ) solar cells. The power conversion efficiency (PCE) of the devices based on P:PCBM and P:F cast from 1.2-dichlorobenzene (DCB) was found to be 1.40% and 2.32%, resp. The higher value of PCE for the device with P:F as compared to P:PCBM is attributed to the increase in both short circuit current (J _sc) and open circuit voltage (V_oc). The increase in the J _sc is due to the stronger light absorption of F in visible region as compared to PCBM, i.e. more exciton generation in the blend. On the other hand, the higher difference between the LUMO levels of P and F, as compared to P and PCBM is responsible for the enhancement in the V_oc. A maximum overall PCE of 4.20% was obtained for the BHJ polymer cell based on the active layer (P:F) deposited from mixed solvents 1-chloronaphthalene/1,2-dichlorobenzene (CN/DCB) and subsequent thermal annealing at 120 °C. This improvement in the PCE has been attributed to the enhanced crystallinity of the blend and more balanced charge transport in the device due to the thermal treatment.

Solar Energy Materials & Solar Cells 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, Formula: C4Br2N2O4S.

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

Bugera, Maksym published the artcileDeoxofluorination of Aliphatic Carboxylic Acids: A Route to Trifluoromethyl-Substituted Derivatives, Name: 3-Bromo-2-methylpropanoic acid, the publication is Journal of Organic Chemistry (2019), 84(24), 16105-16115, database is CAplus and MEDLINE.

A practical method for the synthesis of functionalized aliphatic trifluoromethyl-substituted derivatives from aliphatic acids was developed. The transformation proceeds with sulfur tetrafluoride in the presence of water as a key additive. Compared to previous methods, the reaction gives products with full retention of stereo- and absolute configuration of chiral centers.

Journal of Organic Chemistry published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, Name: 3-Bromo-2-methylpropanoic acid.

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

Cain, Caitlin N. published the artcileTile-Based Pairwise Analysis of GC x GC-TOFMS Data to Facilitate Analyte Discovery and Mass Spectrum Purification, Recommanded Product: 1-Bromooctane, the publication is Analytical Chemistry (Washington, DC, United States) (2022), 94(14), 5658-5666, database is CAplus and MEDLINE.

A new tile-based pairwise anal. workflow, termed 1v1 anal., is presented to discover and identify analytes that differentiate two chromatograms collected using comprehensive two-dimensional (2D) gas chromatog. coupled with time-of-flight mass spectrometry (GC x GC-TOFMS). Tile-based 1v1 anal. easily discovered all 18 non-native analytes spiked in diesel fuel within the top 30 hits, outperforming standard pairwise chromatog. analyses. However, eight spiked analytes could not be identified with multivariate curve resolution-alternating least-squares (MCR-ALS) nor parallel factor anal. (PARAFAC) due to background contamination. Analyte identification was achieved with class comparison enabled-mass spectrum purification (CCE-MSP), which obtains a pure analyte spectrum by normalizing the spectra to an interferent mass channel (m/z) identified from 1v1 anal. and subtracting the two spectra. This report also details the development of CCE-MSP assisted MCR-ALS, which removes the identified interferent m/z from the data prior to decomposition In total, 17 out of 18 spiked analytes had a match value (MV) > 800 with both versions of CCE-MSP. For example, MCR-ALS and PARAFAC were unable to decompose the pure spectrum of Me decanoate (MVs < 200) due to its low 2D chromatog. resolution (~0.34) and high interferent-to-analyte signal ratio (~30:1). By leveraging information gained from 1v1 anal., CCE-MSP and CCE-MSP assisted MCR-ALS obtained a pure spectrum with an average MV of 908 and 964, resp. Furthermore, tile-based 1v1 anal. was applied to track moisture damage in cacao beans, where 86 analytes with at least a 2-fold concentration change were discovered between the unmolded and molded samples. This 1v1 anal. workflow is beneficial for studies where multiple replicates are either unavailable or undesirable to save anal. time.

Analytical Chemistry (Washington, DC, United States) 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, Recommanded Product: 1-Bromooctane.

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

Czollner, Laszlo published the artcileSynthesis of galanthamine, Product Details of C10H16Br3N, the publication is ARKIVOC (Gainesville, FL, United States) [online computer file] (2001), 191-200, database is CAplus.

The synthesis of (±)- and (-)-galanthamine (I) via 3,4-dihydro-6,7-dimethoxy-4′-oxo[spiro-[5H]-2-benzazepine-5,1′-[2]cyclohexene]-2(1H)-carboxylic acid Et ester (II) is described.

ARKIVOC (Gainesville, FL, United States) [online computer file] 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, Product Details of C10H16Br3N.

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

Hartrampf, Felix W. W. published the artcileTotal Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization, Synthetic Route of 69361-41-7, the publication is Journal of Organic Chemistry (2017), 82(15), 8206-8212, database is CAplus and MEDLINE.

A concise, enantioselective synthesis of lycopladine A and carinatine A is presented. Our synthetic approach hinges on the recently developed mild carbocyclization of ynones to furnish the hydrindane core of the alkaloids. Their pyridine ring was efficiently installed using the Ciufolini method. Both heterocycles of carinatine A, a rare naturally occurring nitrone, were formed in a single operation.

Journal of 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, Synthetic Route of 69361-41-7.

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