Tag: 100-200

Benzopolymethylene compounds. IV. The two ar-aldehydes of tetralin was written by Braun, Julius V.;Moldaenke, K.;Dirlam, H.;Gruber, H.. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1922.HPLC of Formula: 29809-13-0 This article mentions the following:

When tetralin (A) is treated with CO and HCl in the presence of AlCl₃ it is impossible to prevent the greater part of the A from condensing with itself in the same way as it does with AlCl₃ alone (Schroeter, C. A. 15, 525); the small part that does react with the CO and HCl gives exclusively the ar-tetralin-β-aldehyde (B) (2 g. from 100 g. A). Both B and the α-isomer (C) can be obtained from the ar-tetralin-β- and α-methylamines (D and E, resp.) through the corresponding alcs. Bamberger and Lodter’s statement that α-C₁₀H₇CH₂NH₂ on reduction takes up the H in the substituted nucleus (Ber. 20, 1708(1887)) seemed to exclude this compound and the β-isomer as the starting points in the synthesis of B and C. Accordingly the NH₂ group in the α- and β-tetralylamines was replaced by CN, which was then reduced to CH₂NH₂, but the yields are poor. On repeating B.’s work, however, it was found that it is the unsubstituted nucleus which takes up the H on reduction and that the pure D and E can easily be obtained in this way. ar-α-Tetralyl cyanide, obtained in 22% yield from the amine by the Sandmeyer reaction, b₁₅ 153°, solidifies to a yellowish crystalline mass m. 48° (Bamberger and Bordt, Ber. 22, 625(1889), describe it as an oil b₁₂₁ 277-9°, which does not solidify), hydrolyzed by fuming HCl in a sealed tube at 120° to the acid, m. 150° (B. and H. give 123°); reduction of the nitrile with Na and alc. gives chiefly A and only about 1/3 is converted into E, oil of basic odor, b₁₁ 149-52°, eagerly absorbs CO₂ from the air, also obtained in almost 90% yield from α-C₁₀H₇CH₂NH₂ with 8 atoms of Na in AmOH (in EtOH there is very little reaction); hydrochloride, silvery needles from alc., m. 253°; picrate, golden yellow prisms from alc., m. 242°; acetyl derivative, m. 125°; benzoyl derivative, m. 144°; phenylurea, m. 199°; phenylthiourea, m. 153°. The corresponding ar-α-tetralylmethylamine (from α-C₁₀H₇CN with Na and alc.) forms a hydrochloride m. 230°, picrate m. 169-70°, phenylurea m. 126°, and benzoyl derivative m. 125°. ar-β-Tetralyl cyanide (obtained in 45-60% yield), liquid of a not unpleasant odor, b₁₁ 151-2°, m. 20-1°, gives with Na and EtOH 30% of D, b₁₁ 146-8°; hydrochloride, m. 248°; picrate, m. 215°; benzoyl derivative, long needles from alc., m. 165°, b₁₀ 260-5°; p-nitrobenzoyl derivative, m. 170°; phenylthiourea, m. 130°. D is also obtained in almost 90% yield from β-C₁₀H₇CH₂NH₂ with Na and AmOH. ar-α-Tetralylcarbinol, obtained in 80% yield from E diazotized in AcOH with the calculated amount of NaNO₂ and heated on the H₂O bath until the evolution of gas ceases, b₁₂ 154-5°, gives in H₂SO₄ with the calculated amount of K₂Cr₂O₇ 1/3 of its weight of C, b₁₂ 131-3°, as an almost odorless oil; semicarbazone, m. 187°. KMnO₄ smoothly oxidizes C to the acid. ar-β-Tetralylcarbinol (yield, 70%), faintly yellow liquid with a strong pleasant odor, b₁₄ 148-52°, gives on oxidation 25% of B, liquid of characteristic peppermint-like odor, b₁₄ 138°; semicarbazone, m. 219°. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0HPLC of Formula: 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.HPLC of Formula: 29809-13-0

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Synthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor was written by Milicevic Sephton, Selena;Vetterli, Peter T.;Pedani, Valentina;Cermak, Stjepko;Chiotellis, Aristeidis;Roscales, Sylvia;Mueller Herde, Adrienne;Schibli, Roger;Auberson, Yves P.;Ametamey, Simon M.. And the article was included in Helvetica Chimica Acta in 2017.Formula: C8H6N2O2 This article mentions the following:

Due to the biol. complexity of the N-methyl-D-aspartate receptor (NMDAR), the development of a positron emission tomog. radiotracer for the imaging of NMDAR has met with limited success. Recent studies have established the presence of GluN2A subunit of the NMDAR in the heart and its role in the regulation of intracellular calcium levels. In our efforts to develop an imaging agent for the GluN2A subunit, we designed three new compounds based on a quinoxaline scaffold. The synthesis of the analogs was based on a two-step Kabachnik-Fields reaction in sequence with Suzuki cross-coupling and acid hydrolysis. They exhibited comparable high binding affinity values below 5 nM. A two-step radiolabeling procedure was successfully developed for the synthesis of [¹⁸F]I. [¹⁸F]I was obtained in a modest overall radiochem. yield of 5.5 ± 4.2%, a good specific radioactivity of 254 ± 158 GBq/μmol, and a radiochem. purity > 99%. While two compounds showed comparable binding affinity towards NMDAR, sluggish radiolabeling, prevented their further evaluation. For [¹⁸F]I, in vitro autoradiog. on rat heart slices demonstrated heterogeneous but unspecific accumulation, whereas for the brain a high in vitro specificity towards NMDAR, could be demonstrated. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Formula: C8H6N2O2).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Formula: C8H6N2O2

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Solid phase synthesis of functionalized indazoles using triazenes – scope and limitations was written by Garcia, Ana Maria;Jung, Nicole;Gil, Carmen;Nieger, Martin;Braese, Stefan. And the article was included in RSC Advances in 2015.Safety of 2-Amino-3-chlorobenzonitrile This article mentions the following:

A modular synthesis of highly substituted indazoles via a strategy on solid supports was discussed. The heterocyclic nitrogen atoms originated from diazonium salts, being cleaved from triazene containing resins. The scope and limitations of this process was explored, considering especially the competitive occurrence of triazines and the cleavage of hydrolyzed and traceless side products. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Safety of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Safety of 2-Amino-3-chlorobenzonitrile

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Synthesis of trifluoromethyl-substituted phenylene diisocyanates was written by Inukai, Kan;Maki, Yasuo. And the article was included in Kogyo Kagaku Zasshi in 1965.HPLC of Formula: 1483-54-1 This article mentions the following:

F₃CC₆H₃(NCO)₂ were synthesized from the corresponding F₃CC₆H₃Br₂ through F₃CC₆H₃(CN)₂ → F₃CC₆H₃(CO₂H)₂. Thus, a mixture of 30.4 g. 2,4-F₃CC₆H₃Br₂ and 19.8 g. CuCN in 30 ml. HCONMe₂ was heated at 150° 3 hrs., 60 g. FeCl₃, 15 ml. concentrated HCl, and 90 ml. H₂O added, the whole heated at 60-70° 2 hrs., filtered, the precipitates extracted with hot EtOH to give 2,4-F₃CC₆H₃(CN)₂, pale yellow crystals, m. 106-7° (80% EtOH), in 93% yield. Similarly, 2,5-F₃CC₆H₃(CN)₂, pale yellow crystals, m. 101-2° (90% EtOH) was obtained in 68% yield and 3,4-F₃CC₆H₃(CN)₂, prisms, m. 113-14° (sublimation), in 10% yield. F₃CC₆(CO₂H)₂ was prepared by heating 25.5 g. F₃CC₆H₃(CN)₂, 25 ml. concentrated HCl, and 17 ml. AcOH in a sealed tube at 135-40° 10-15 hrs. (compound % yield, and m.p. given): 2,4-F₃CC₆H₃(CO₂H)₂, 72, 240-1° (EtOH); 2,5-F₃CC₆H₃(CO₂H), 68, sublimed; 3,4-F₃CC₆H₃(CO₂H)₂, 74, 264-5° (EtOH). F₃CC₆H₃(COCl)₂ was prepared by heating 23.4 g. F₃CC₆H₃(CO₂H)₂ and 80 g. SOCl₂ 5 hrs. (compound, % yield, b₁₀, n²⁰_D, and d₂₀ given): 2,4-F₃CC₆H₃(COCl)₂, 68, 119-20°, 1.5136, 1.5154; 2,5-F₃CC₆H₃(COCl)₂, 92, 115-16°, 1.5137, 1.5087; 3,4-F₃CC₆H₃(COCl)₂, 69, 108-9°, 1.5174, 1.5002. F₃CC₆H₃(NCO)₂ was prepared by heating 27.0 g. F₃CC₆H₃(COCl)₂ and 15.0 g. NaN₃ in 60 ml. xylene under N atm. with stirring 12-13 hrs. (compound, % yield, b.p., m.p., n²⁰_D, and d₂₀ given): 2,4-F₃CC₆H₃(NCO)₂, 58, 104-5°/5 mm., 36-7°, –, –. 2,5-F₃CC₆H₃(NCO)₂, 32, 103-4°/5 mm., –, 1.5202, 1.4398; 3,4-F₃CC₆H₃(NCO)₂, 80, 111-12°/11 mm., –, 1.5298, 1.4491. 3,4-F₃CC₆H₃(NCO)₂ was synthesized from 3,4-F₃CC₆H₃(NH₂)Br through 3,4-F₃CC₆H₃(CN)Br → 3,4-F₃CC₆H₃(CO₂H)Br → 3,4-F₃CC₆H₃(CO₂H)CN → 3,4-F₃CC₆H₃(CO₂H)₂. 3,4-F₃CC₆H₃(NH₂)CN, yellow crystals, b₇ 108-10°, m. 24-5°, was prepared in 26% yield by heating 30.0 g. 3,4-F₃CC₆H₃(NH₂)Br and 13.4 g. CuCN in 18 ml. HCONMe₂ 4 hrs. 3,4-F₃CC₆H₃(CN)Br, m. 43-4° (petr. ether), was prepared in 40% yield by heating ZnCl₂-diazonium salt of 24.0 g. 3,4-F₃CC₆H₃(NH₂)Br with 6.3 g. NaCN, 0.5 g. CuCN, 10 g. NaHCO₃, 100 ml. H₂O, and 50 ml. petr. ether with stirring for 2 hrs. Similarly, 3,4-F₃CC₆H₃(CO₂H)Br, m. 116-17° (petr. ether), and 3,4-F₃CC₆H₃(CO₂H)CN, m. 169-70° (EtOH), were obtained in 49% and 89% yield, resp. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1HPLC of Formula: 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 1483-54-1

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Synthesis and mesomorphic properties of some 3-substituted-4-cyanophenyl esters, 4′-cyano-3-substituted-4-biphenyl esters of 4-(trans-4-alkylcyclohexyl) benzoic, 4-alkyl-1,3-substituted biphenyl-4′-carboxylic, trans-4-alkylcyclohexanecarboxylic and 4-alkylbenzoic acids and electrooptic parameters of liquid-crystalline mixtures containing these compounds was written by Bezborodov, V. S.;Lapanik, V. I.;Adomenas, P.;Sirutkaitis, R.. And the article was included in Liquid Crystals in 1992.Computed Properties of C7H4BrNO This article mentions the following:

The reaction of trans-4-alkylcyclohexanecarboxylic acid chlorides, 4-alkylbenzoic, 4-(trans-4-alkylcyclohexyl)-benzoic, 4-alkyl-3-substituted biphenyl-4′-carboxylic acids with 4-hydroxy-3′-substituted benzonitriles and 4-hydroxy-3′-substituted-4′-cyanobiphenyls produced the corresponding esters. The mesomorphic properties of the esters and electrooptic and dynamic parameters of the mixtures containing these compound were studied. The liquid-crystalline mixtures containing 4-cyano-3-substituted-4′-biphenyl esters of 4-alkylbenzoic and trans-4-alkyl-cyclohexanecarboxylic acids have higher threshold voltages and saturation voltages in comparison with the analogous mixtures containing 4-cyano-3-substituted Ph esters of 4-(trans-4-alkylcyclohexyl)benzoic acids. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Computed Properties of C7H4BrNO).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C7H4BrNO

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Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as New Potent Anticancer Agents was written by Romagnoli, Romeo;Baraldi, Pier Giovanni;Kimatrai Salvador, Maria;Preti, Delia;Aghazadeh Tabrizi, Mojgan;Bassetto, Marcella;Brancale, Andrea;Hamel, Ernest;Castagliuolo, Ignazio;Bortolozzi, Roberta;Basso, Giuseppe;Viola, Giampietro. And the article was included in Journal of Medicinal Chemistry in 2013.HPLC of Formula: 64113-86-6 This article mentions the following:

Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3′,4′,5′-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine mol. skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the Me group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the Me was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the Me group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds I and II did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound I significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 64113-86-6

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Iron-Catalyzed Tandem Radical Addition/Cyclization: Highly Efficient Access to Methylated Quinoline-2,4-diones was written by Sun, Huan;Jiang, Yue;Lu, Ming-Kun;Li, Yun-Yun;Li, Li;Liu, Ji-Kai. And the article was included in Synlett in 2020.Product Details of 1483-54-1 This article mentions the following:

A visible-light-induced and iron-catalyzed oxidative radical addition/cyclization cascade reaction of N-(o-cyanoaryl)acrylamides I [R¹ = 4-Cl, 5-CF₃, 3-Br, etc.; R² = Me, Bn; R³ = Me, [(2,2-dimethylpropanoyl)oxy]methyl, Bn, Ph, (acetyloxy)methyl, (1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl] with DMSO has been developed. The method exhibits a wide substrate scope and an excellent functional-group tolerance, thus providing an efficient and convenient access to a variety of methylated quinoline-2,4-diones II (R⁴ = 6-Cl, 6-CF₃, 5-Br, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Product Details of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Product Details of 1483-54-1

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Cobalt in N-doped carbon matrix catalyst for chemoselective hydrogenation of nitroarenes was written by Dai, Yihu;Jiang, Chunyang;Xu, Min;Bian, Bo;Lu, Di;Yang, Yanhui. And the article was included in Applied Catalysis, A: General in 2019.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Anilines as important intermediates for both organic synthesis and industrial manufactory are densely substituted with a variety of functional moieties, and the transformation of nitroarenes into corresponding anilines requires catalytically selective hydrogenation catalyst. Herein, we describe a simple pyrolysis strategy to prepare cobalt catalysts in nitrogen-doped carbon matrix applied in the selective hydrogenation of nitroarenes with mol. hydrogen. The Co/NC catalysts are obtained through thermal treatment of mixed precursors of cobalt phthalocyanine and melamine. The surface-modified Co particles with Co₃O₄ and CoNx sites are surrounded by N-doped carbon layers according to a series of structural characterization results. These Co/NC catalysts are capable of efficiently selective hydrogenation of nitrobenzene and various substituted nitroarenes into corresponding anilines under relatively mild reaction conditions. The optimal catalytic hydrogenation performance is contributed to the fast rate of H₂ dissociated activation on the CoN_x active sites and the facile adsorption of the reactant substances, which is verified by the isotopic H₂-D₂ exchange experiments, reactant adsorption and the ORR reaction tests. Furthermore, the heterogeneous Co/NC catalyst is highly stable without the Co leaching and deactivation issues during the recycling reaction runs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile

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Anodic cyanation of tert-butylated anisoles: competitive aromatic additions and substitutions was written by Yoshida, Kunihisa;Takeda, Kazusada;Fueno, Takayuki. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1993.Computed Properties of C11H13N This article mentions the following:

The electrooxidation of several tert-butylated anisoles has been carried out in methanol containing sodium cyanide at a Pt anode in a divided cell. Two types of reactions occurred competitively, aromatic-ring addition and substitution. Increasing the level of tert-Bu substitution raises the relative extent of addition to the aromatic ring. The order of orientational preference for substitution of the aromatic hydrogen of alkylanisole cation radicals is explained in terms of the LUMO electron densities calculated for the cation radicals. The effect of structure on the oxidation potential of alkylanisoles has also been studied. Para substitution lowers the oxidation potential while ortho substitution raises the potential. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Computed Properties of C11H13N).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Computed Properties of C11H13N

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Iridium-catalyzed α-alkylation of acetonitrile with primary and secondary alcohols was written by Sawaguchi, Takuya;Obora, Yasushi. And the article was included in Chemistry Letters in 2011.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

Acetonitrile is successfully alkylated with primary and secondary alcs. in the presence of t-BuOK using [Ir(OH)(cod)]₂ as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chem. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application In Synthesis of 2-Cyclohexylacetonitrile

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