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[ CAS No. 32281-97-3 ] {[proInfo.proName]}

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Chemical Structure| 32281-97-3
Chemical Structure| 32281-97-3
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Product Citations

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Jennifer Doan Tran ;

Abstract: As climate change continues to be a global issue due to its negative environmental impact, various countries have made great efforts to integrate more renewable energy into the power-grid. Using renewable energy can lower dependency on fossil fuels but, there are issues that limit switching from consuming fossil fuels to renewable energy. In the case of solar or wind technology, the energy harnessed is not consistent throughout the day. By pairing renewable energy with redox flow batteries (RFBs), this can address the issue of inconsistent energy. Through RFBs, excess energy generated by renewable energy can be stored by electrochemical bonds. The focus of this research is to synthesize a water-soluble bislawsone to use as a redox active material for RFBs using 7-bromo-3,4-dihydro-2H-naphthalen-1-one. 2,2’-bis(3-hydroxy-7-methoxy-N,N,N-trimethylethanaminium chloride-1,4-naphthoquinone) was made but was not purified. The crude product was used in cyclic voltammetry (CV) testing. As a baseline, 5 mM of 7,7’-dibromo-2,2’-bis(3-hydroxy-1,4-naphthoquinone) was added to 1M KOH and the CV was measured. The potential was measured at -0.637 V. The electrolytic solution consisted of 5 mM of redox active material with 1M KCl in water adjusted to pH 7. There was no measurement. The second electrolytic solution consisted of 5 mM of redox active material with 1M KCl in 1M KOH. The potential was measured at -0.628 V. Solubility decreased by adding supporting salts and at pH 7. This suggests that adding a water-soluble group on bislawsone influences solubility and solubility affects voltage potential.

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Product Details of [ 32281-97-3 ]

CAS No. :32281-97-3 MDL No. :MFCD02179287
Formula : C10H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :YGVDCGFUUUJCDF-UHFFFAOYSA-N
M.W : 225.08 Pubchem ID :252731
Synonyms :
Chemical Name :7-Bromo-3,4-dihydronaphthalen-1(2H)-one

Calculated chemistry of [ 32281-97-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.0
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.97
Log Po/w (MLOGP) : 2.71
Log Po/w (SILICOS-IT) : 3.68
Consensus Log Po/w : 2.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.31
Solubility : 0.11 mg/ml ; 0.000487 mol/l
Class : Soluble
Log S (Ali) : -2.72
Solubility : 0.427 mg/ml ; 0.0019 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.25
Solubility : 0.0125 mg/ml ; 0.0000557 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 32281-97-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273 UN#:N/A
Hazard Statements:H302-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 32281-97-3 ]

* 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 [ 32281-97-3 ]

[ 32281-97-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 32281-97-3 ]
  • [ 2243-58-5 ]
  • 9-bromo-12,13-dihydro-7<i>H</i>-dibenzo[<i>a,g</i>]carbazole [ No CAS ]
  • 2
  • [ 32281-97-3 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
56% Step D: A solution of tetrabutylammonium tribromide (11.8 g, 24.4 mmol) in dichloromethane (80 ml) was added dropwise to a solution of the product from Step C (5.0 g, 22.2 mmol) in dichloromethane (20 ml) and methanol (20 ml) at room temperature over 1 hour. At completion of the addition, the mixture was stirred at room temperature for 15 hours and was then concentrated. The residue was taken into dichloromethane and was washed with saturated sodium bicarbonate three times. The organic layer was concentrated and the residue was dissolved in dimethylformamide (100 ml). Lithium carbonate (5.3 g, 71.1 mmol) and lithium bromide (4.1 g, 46.6 mmol) were added and the resulting mixture was stirred at 140° C. for 1.5 hours. After cooling to room temperature, the solids were filtered and rinsed with ethyl acetate. The filtrate was washed with water four times and dried over sodium sulfate to give 7-bromonaphthalen-1-ol (2.7 g, 56percent): 1H NMR (300 MHz, CDCl3) delta 8.41 (d, J=1.8 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.57 (dd, J=8.7, 1.8 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.28-7.35 (m, 1H), 6.62 (d, J=7.2 Hz, 1H), 5.80 (br s, 1H).
  • 3
  • [ 5417-17-4 ]
  • [ 32281-97-3 ]
  • C19H16BrClO3 [ No CAS ]
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Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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