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Chemical Structure| 130-15-4 Chemical Structure| 130-15-4
Chemical Structure| 130-15-4

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A choleretic.

Synonyms: P-Naphthoquinone; α-Naphthoquinone; para-naphthoquinone

4.5 *For Research Use Only !

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Product Citations

Product Citations

Emily Penn ; Antonio Baclig ; Devi Ganapathi ; William C. Chueh ;

Abstract: Eutectic electrolytes can attain high concentrations of redox-active species, offering a path toward high energy density redox flow batteries. Here we introduce a new entropically-driven eutectic mixing approach using organic small molecules. By mixing chemically similar redox-active species, we engineer highly concentrated, low viscosity liquids composed almost entirely of redox-active molecules. Using quinones as a model system, we discover a ternary benzoquinone eutectic mixture and a binary naphthoquinone eutectic mixture which have theoretical redox-active electron concentrations of 16.8 and 8.8 M e–, respectively. We investigate compatibility with protic supporting electrolytes and quantify ionic conductivity and viscosity of quinone eutectic electrolytes across multiple states of charge. A binary naphthoquinone eutectic electrolyte with a protic ionic liquid supporting electrolyte (7.1 M e–, theoretical volumetric capacity 188 Ah L–1) achieves a volumetric capacity of 49 Ah L–1 in symmetric static cell cycling. These preliminary results suggest that entropy-driven eutectic mixing is a promising strategy for developing high-energy density flow battery electrolytes.

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Alternative Products

Product Details of 1,4-Naphthoquinone

CAS No. :130-15-4
Formula : C10H6O2
M.W : 158.15
SMILES Code : O=C1C=CC(C2=C1C=CC=C2)=O
Synonyms :
P-Naphthoquinone; α-Naphthoquinone; para-naphthoquinone
MDL No. :MFCD00001676
InChI Key :FRASJONUBLZVQX-UHFFFAOYSA-N
Pubchem ID :8530

Safety of 1,4-Naphthoquinone

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H317-H331-H335-H410-H301+H311
Precautionary Statements:P272-P280-P264-P270-P271-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P405-P501
Class:8(6.1)
UN#:2923
Packing Group:

Application In Synthesis of 1,4-Naphthoquinone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 130-15-4 ]

[ 130-15-4 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 24454-89-5 ]
  • [ 123-31-9 ]
  • [ 130-15-4 ]
  • [ 605-32-3 ]
  • 2
  • [ 1195-33-1 ]
  • [ 130-15-4 ]
  • 2-(4-bromo-benzenesulfonyl)-naphthalene-1,4-diol [ No CAS ]
  • 3
  • [ 35202-54-1 ]
  • [ 130-15-4 ]
  • [ 53995-99-6 ]
  • 4
  • [ 31411-71-9 ]
  • [ 130-15-4 ]
  • [ 605-32-3 ]
  • [ 483-35-2 ]
  • 5
  • [ 1004-38-2 ]
  • [ 130-15-4 ]
  • 7,9-diamino-11<i>H</i>-8,10,11-triaza-benzo[<i>a</i>]fluoren-5-ol [ No CAS ]
  • 6
  • 2-Nitro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene [ No CAS ]
  • [ 130-15-4 ]
  • [ 3846-71-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; sodium; sodium hydrogensulfite; In water; isopropyl alcohol; EXAMPLE 2 A suspension of 9.2 g of sodium in 400 g of isopropanol is refluxed in a 1.5 liter sulfonating flask until a solution is formed. To this are added, at 60° C., 3.2 g of 1,4-naphthoquinone, 2.1 g of sodium bisulfite and 71 g of 2-nitro-2'-hydroxy-3',5'-bis-tert.-butylazobenzene. The mixture is stirred at 60° C. for between half an hour and a full hour. 20 g of 17 percent by volume aqueous sulfuric acid and 100 ml of warm water at 60°-70° C. are then added dropwise. The precipitated crystals are filtered and are washed with warm 60 percent by weight aqueous methanol and with warm water. Drying at 70°-80° C. n vacuo produces 2,4-di-tert.-butyl-6-(2'-benzotriazolyl)-phenol in a high yield.
With sodium hydroxide; sulfuric acid; sodium hydrogensulfite; In water; isopropyl alcohol; EXAMPLE 5 200 g of isopropanol are heated to 60° C. in a 750 ml sulfonating flask, and 1 g of sodium bisulfite, 1.6 g of 1,4-naphthoquinone, 14 g of sodium hydroxide and 35.5 g of 2-nitro-2'-hydroxy-3',5'-bis-tert.-butylazobenzene are then added. The mixture is stirred at 75°-80° C. for two hours, and 18 g of 17 percent by volume aqueous sulfuric acid and 50 ml of warm water are then added dropwise. The precipitated crystals are washed with warm methanol and then with warm water. The product is a high yield of 2,4-di-tert.-butyl-6-(2'-benzotriazolyl)-phenol.
  • 7
  • [ 2840-44-0 ]
  • [ 130-15-4 ]
YieldReaction ConditionsOperation in experiment
5.6g (37%) Autoxidation of <strong>[2840-44-0]7-fluoro-1-tetralone</strong> (13g) as described in example 8(b) gave 5.6g (37percent) of the naphthoquinone which after recrystallization from chloroform had m.p. 206°-210° C. (Found; C, 62.50; H, 2.70; C10 H5 FO3 requires; C, 62.51; H, 2.62percent).
  • 8
  • [ 52522-40-4 ]
  • [ 5259-72-3 ]
  • [ 130-15-4 ]
  • [ 544707-91-7 ]
  • 9
  • [ 52522-40-4 ]
  • [ 130-15-4 ]
  • bis(1,4-naphthoquinone)palladium(0) [ No CAS ]
  • 10
  • [ 52522-40-4 ]
  • [ 130-15-4 ]
  • [ 478548-99-1 ]
  • [ 1083211-26-0 ]
YieldReaction ConditionsOperation in experiment
89% In acetone; at 20℃; for 1h;Inert atmosphere; 0.1328 g (0.4057 mmol) of 8-diphenylphosphine-2-methylquinoline, 0.0674 g (0.4261 mmol) of naphthoquinone and 0.2003 g(0.1935 mmol) of [Pd2(DBA)3CHCl3] were dissolved under inert atmosphere (Ar) in 30 ml of anhydrous acetone in a 100 ml necked flask. The mixture was stirred for 60 min at RT, the resulting orange solution treated with activated charcoal, filtered on a celite filter and concentrated under vacuum. The title complexwas precipitated as a paleorange solid by slow addition of diethylether, filtered off on a gooch, and washed with diethylether and n-pentane. 0.2039g (yield 89percent) of complex 1'b was obtained. 1H-NMR (300 MHz, CDCl3, T = 298 K, ppm) delta: 3.12 (s, 3H, quinoline-CH3), 4.98-5.05 (m, 2H, CH=CH) 7.06e7.13 (m, 2H, aryl naphthoquinone), 7.29-7.71 (m, 13H, H3, PPh2, aryl naphthoquinone), 7.79 (ddd,1H, J = 8.1, 7.5,1.4 Hz, H6), 7.90 (d,1H, J = 8.1, H7), 8.05 (dd, 1H, J = 7.5, 1.6 Hz, H5), 8.19 (dd, 1H, J = 8.4, 1.4 Hz, H4). 13C{1H}-NMR (CDCl3, T = 298 K, ppm) delta: 30.3 (CH3, quinoline-CH3), 62.7 (CH, CH=CH trans-N), 66.3 (d, CH, JCP = 21 Hz, CH=CH transP), 123.9 (CH, C3), 125.1 (CH, C5), 131.1 (CH, C7), 137.8 (CH, C6), 138.4 (CH, C4), 165.7 (d, C, JCP = 22.1 Hz, C9),165.7 (C, C2),184.0 (d, C, JCP = 6.2 Hz, CO transP), 185.2 (C, CO transN). 31P{1H}-NMR (CD2Cl2, T = 298 K, ppm) delta: 23.4. IR (KBr, pellet, cm-1): 1641 (nCO). Anal. Calcd. for C32H24NO2PPd: C 64.93, H 4.09, N 2.37. Found: C 65.06, H 3.98, N 2.21.
  • 11
  • [ 52522-40-4 ]
  • [ 28225-52-7 ]
  • [ 130-15-4 ]
  • [ 1132766-64-3 ]
  • 12
  • [ 570-02-5 ]
  • [ 130-15-4 ]
  • [ 1258168-11-4 ]
  • 13
  • [ 367-34-0 ]
  • [ 130-15-4 ]
  • [ 1276184-21-4 ]
YieldReaction ConditionsOperation in experiment
70% With copper diacetate; acetic acid; at 70℃; for 2h; General procedure: The substituted naphthoquinones were prepared by the method reported in the literature with several modifications [9]. 1,4-Naphthoquinone (1 mmol), a substituted aniline (1 mmol) and an amount (0.1 mmol) of Cu(AcO)2 were solubilized by gently warming in AcOH (2 mL) for 30 min. The reaction mixture was gently warmed in a water bath for two hours at 70 °C. The solid that precipitated was separated by filtration and washed with an aqueous solution of NaHCO3 (10 percent) to neutralize the remaining acid. The reaction mixture was dissolved in a small amount of CH2Cl2 and was passed through a small silica gel column to remove the remaining copper salts. 4.9 Characterization of 2-(<strong>[367-34-0]2,4,5-trifluoroaniline</strong>)-1,4-naphthoquinone (3h) 1H (400MHz, DMSO-d6): delta 5.62 (d, 1H, 3, J=3.1Hz), 7.63 (dt, 1H, 6?, JoHF=10.8Hz, JmHF=7.9Hz), 7.76 (td, 2H, 3?, JoHF=10Hz, JmHF=7.4Hz), 7.80 (td, 1H, 7, Jo=7.5Hz, Jm=1.4Hz), 7.87 (td, 1H, 6, Jo=7.5Hz, Jm=1.3Hz), 7.95 (dd, 1H, 5, Jo=7.6Hz, Jm=0.98Hz), 8.07 (dd, 1H, 8, Jo=7.61Hz, Jm=0.97Hz), 9.12 (s, 1H, A); 13C{1H} (100MHz, DMSO-d6): delta 103.68 (3), 106.95 (dd, 3?, 2JC?F=26Hz, 2JC?F=22Hz), 116.19 (d, 6?, 2JC?F=20Hz), 122.06 (m, 1?), 125.40 (5), 126.12 (8), 130.27 (9), 132.34 (10), 132.87 (7), 134.97 (6), 145.92 (dm, 4?, 1JC?F=240Hz) [22], 146.69 (2), 147.64 (dm, 5?, 1JC?F=235Hz) [22], 151.92 (dd, 2?, 1JC?F=247Hz, 3JC?F=11Hz), 180.97 (1), 182.55 (4); High-Resolution EI-MS C16H8F3NO2 m/z calcd: 303.0507, found: 303.0507.
General procedure: These compounds were prepared by a method previously reported in the literature by us [38?41]. 1,4-Naphthoquinone or 5-hydroxy-1,4-naphthoquinone (1 mmol) was dissolved in ethanol (10 mL) and an amount (0.1 mmol) of catalyst (FeCl3 or CeCl3) was added. The reaction mixture was stirred for 15 min to allow the reaction between the Lewis base (1,4-naphthoquinone) and catalyst. A solution of the substituted aniline (1 mmol) in ethanol (10 mL) was slowly added and the mixture was refluxed for 4 h. TLC analysis indicated only one product was formed. The resulting solid was filtered, washed with cold ethanol and recrystallized from ethanol. Total characterization of compounds 3a?k has been previously reported [38?41].
  • 14
  • [ 75-15-0 ]
  • [ 6519-67-1 ]
  • [ 130-15-4 ]
  • ethyl 2-(4,9-dioxo-4,9-dihydronaphtho[2,3-d][1,3]dithiol-2-imino)-2-(1H-indol-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.2% With triethylamine; In dichloromethane; at 0℃; for 4h; General procedure: Typically, a mixture of 1,4-naphthoquinone (1a, 1.0 mmol, 0.158 g, 1.0 equiv), phenylalanine ethyl ester hydrochloride (2a, 1.2 mmol, 0.276 g, 1.2 equiv), CS2 (3a, 5 mmol, 0.381 g, 5.0 equiv), triethylamine (1.2 mmol, 0.121 g 1.2 equiv) in CH2Cl2 (5.0 mL) was stirred at 0 C under air condition for 4 h, determined by GC-MS and TLC. The solvent was removed under vacuum and the resulting crude product was purified by chromatography on silica gel eluted using CH2Cl2 as the eluent to afford the desired product 4a as red solid (0.3735 g, yield 88.2%, mp=149-150 C).
  • 15
  • [ 52522-40-4 ]
  • [ 130-15-4 ]
  • [ 653570-21-9 ]
  • [Pd(η2-naphthoquinone)(2-methyl-8-(tert-butylthio)quinoline)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In acetone; for 0.5h;Inert atmosphere; Darkness; General procedure: To 64.3 mg (0.278 mmol) of TTbQ-Me dissolved in anhydrous acetone (20 ml) in a two necked flask, 30 mg (0.278 mmol) of p-benzoquinone and 120 mg (0.116 mmol) of Pd2DBA3CHCl3 were added in sequence under inert atmosphere (Ar). The resulting mixture was stirred in the dark for 30 min, filtered on a celite filter and evaporated under vacuum to a small volume. Addition of Et2O induces the precipitation of the complex which was filtered off and dried in a desiccator for 5 h. 82.2 mg of the title compound as a red solid were obtained (yield 80percent).
  • 16
  • [ 52522-40-4 ]
  • [ 6575-13-9 ]
  • [ 130-15-4 ]
  • [Pd(η2-naphthoquinone)(Dic)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In acetone; for 0.5h;Inert atmosphere; Darkness; General procedure: To 64.3 mg (0.278 mmol) of TTbQ-Me dissolved in anhydrous acetone (20 ml) in a two necked flask, 30 mg (0.278 mmol) of p-benzoquinone and 120 mg (0.116 mmol) of Pd2DBA3CHCl3 were added in sequence under inert atmosphere (Ar). The resulting mixture was stirred in the dark for 30 min, filtered on a celite filter and evaporated under vacuum to a small volume. Addition of Et2O induces the precipitation of the complex which was filtered off and dried in a desiccator for 5 h. 82.2 mg of the title compound as a red solid were obtained (yield 80percent).
  • 17
  • [ 22237-13-4 ]
  • [ 130-15-4 ]
  • 2-(4-ethoxyphenyl)[1,4]naphthoquinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In dichloromethane; water; at 20℃; for 10h; General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv) and [Cp*RhCl2]2 (0.025 mmol, 5 mol%) in CH2Cl2 (2 mL) was added the boronic acid (0.75 mmol, 1.5 equiv), H2O (1 mL). Then the solution was stirred vigorously at r.t. for 10 h. Upon completion, the reaction was diluted with CH2Cl2 (3 mL) and washed with 5% NaHCO3. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 4 mL), dried over Na2SO4, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (EtOAc-PE, 1:10) to provide the corresponding product.
69% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In dichloromethane; water; at 20℃; for 12h; General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.
  • 18
  • [ 130-15-4 ]
  • [ 53090-43-0 ]
  • ethyl 2-(3,4-dichlorophenyl)-5-hydroxynaphtho[1,2-b]furan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With zinc(II) iodide; In dichloromethane; at 110℃; for 0.5h;Sealed tube; General procedure: 1,4-naphthoquinone (1.5equiv.) ZnI2 (0.7equiv.) and b-keto esters5 a-n (1.0 equiv.) were dissolved in dry CH2Cl2(6 mL) in a 10mLreaction glass vial containing a tiny stirring magnet The vial wassealed tightly with an aluminium-Teflon crimp top and themixture was irradiated for 30 min at a pre-selected temperature of110 C, with an irradiation power of 60W. After the reaction, thevial was cooled to 50 C by gas jet cooling. The crude mixture wasportioned between CH2Cl2 and saturated solution of sodium chloride(6 mL) and the aqueous layer was extracted with methylenchloride (3 6 mL). The combined organic layer were dried onSodium sulfate anhydrous, filtered and the solvent was removedunder reduce pressure. Then, final crude compounds were purifiedby flash chromatography over silica gel.
  • 19
  • [ 14180-51-9 ]
  • [ 76-05-1 ]
  • [ 130-15-4 ]
  • (1,4-dihydroxynaphthalen-2-yl)[bis(4-methoxyphenyl)]phenylphosphonium trifluoroacetate [ No CAS ]
  • 20
  • [ 3469-20-3 ]
  • [ 130-15-4 ]
  • 11-phenyl-1'H-spiro[isoindolo[2,1-a]indole-6,2'-naphthalene]-1',4'(3'H)-dione [ No CAS ]
  • 21
  • [ 30309-80-9 ]
  • [ 130-15-4 ]
  • (4-Bromo-benzyl)-[1-phenyl-meth-(E)-ylidene]-amine [ No CAS ]
  • C31H23BrNO3P [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% Add 0.1 mmol of 1,4-naphthoquinone (R4 = hydrogen) and 0.12 mmol of diphenyl(dialkyl)phosphine oxide (R1 = 2-methylphenyl) into a 10 mL reaction tube. After reacting at 120C for 12 hours, add imine (R=4-bromophenyl) 0.2mmol, copper acetate 0.3mmol, the reaction was carried out at 120C for 12h. After the reaction, the naphthoxazole phosphine oxide compound (R=4-bromophenyl, R1=2-methylphenyl, R4=hydrogen) was separated by column chromatography to obtain a gray solid with a yield of 36%.
  • 22
  • [ 15754-51-5 ]
  • [ 130-15-4 ]
  • (4-Bromo-benzyl)-[1-phenyl-meth-(E)-ylidene]-amine [ No CAS ]
  • C31H23BrNO5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Add 0.1 mmol of 1,4-naphthoquinone (R4 = hydrogen) and 0.12 mmol of diphenyl(dialkyl)phosphine oxide (R1 = 4-methoxyphenyl) into a 10 mL reaction tube. After reacting at 120C for 12 hours, add sub Amine (R=4-bromophenyl) 0.2mmol, copper acetate 0.3mmol, and the reaction was carried out at 120C for 12h. After the reaction, the naphthoxazole phosphine oxide compound (R=4-bromophenyl, R1=4-methoxyphenyl, R4=hydrogen) was separated by column chromatography to obtain a yellow solid with a yield of 61%.
  • 23
  • [ 55577-25-8 ]
  • [ 130-15-4 ]
  • 2-(2-(p-tolyl)-1H-indol-3-yl)naphthalene-1,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.0708333h;Flow reactor; General procedure: Indole derivatives (0.5 mmol, 1 equiv.) and 1,4-naphthoquinone (0.75 mmol, 1.5 equiv.)were dissolved in 2mL CH2Cl2 and pumped into inlet A, Trifluoroacetic acid (00.5equiv.) were dissolved in 2mL CH2Cl2. Inlet A and B were injected simultaneouslythrough 336 cm (2.96 cm3) mixing coil at flow rate 0.7-4.6 mL/min. The temperature ofmixing coil was maintained at room temperature throughout the reaction. The mixturecollected at the outlet was concentrated under vacuum was purified by flash columnchromatography on silica gel (EtOAc/Hexane) to provide pure 3-indolyl-1,4-naphthoquinone(3a-j) (Yield 94-99%, Time 4.25 min.). The flow system was cleaned with3mL of CH2Cl2 in both of inlet A and inlet B before the next reaction.
 

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