1,2-Naphthoquinone

Base Information

• Chemical Name: 1,2-Naphthoquinone
• CAS No.: 524-42-5
• Molecular Formula: C10H6O2
• Molecular Weight: 158.156
• Hs Code.: 2914.69
• European Community (EC) Number: 208-360-2
• NSC Number: 9831
• UN Number: 2811
• UNII: 804K62F61Q
• DSSTox Substance ID: DTXSID2060171
• Nikkaji Number: J6.639G
• Wikipedia: 1,2-Naphthoquinone
• Wikidata: Q171721
• Pharos Ligand ID: SJ1BVCNUXY6Y
• ChEMBL ID: CHEMBL52347
• Mol file: 524-42-5.mol

Synonyms:1,2-naphthoquinone;o-naphthoquinone;ortho-naphthoquinone

Chemical Property of 1,2-Naphthoquinone

Chemical Property:

• Appearance/Colour: brown powder
• Vapor Pressure: 0.00147mmHg at 25°C
• Melting Point: 139-142 °C (dec.)(lit.)
• Refractive Index: 1.617
• Boiling Point: 296.068 °C at 760 mmHg
• Flash Point: 117.376 °C
• PSA: 34.14000
• Density: 1.29 g/cm³
• LogP: 1.46520
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 158.036779430
• Heavy Atom Count: 12
• Complexity: 253
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

1,2-Naphthoquinone(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,C,F
• Hazard Codes: Xn,Xi,C,F
• Statements: 22-36/37/38-34-11-25
• Safety Statements: 26-36-45-36/37/39-16-37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=O)C2=O
• Uses: Chemical reagent and intermediate. 1,2-Naphthquinone is a highly reactive quinone species which aids in modulating cellular homeostasis and electrophilic signal transduction pathways. 1,2-Naphthoquinone was employed as mediator during electrochemical mapping of redox activity in normal human breast (MCF-10A) cells by scanning electrochemical microscopy (SECM).

Technology Process of 1,2-Naphthoquinone

There total 81 articles about 1,2-Naphthoquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,2-Dihydroxynaphthalene (574-00-5) → 1,2-naphthoquinone (524-42-5)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone;

DOI:10.1016/0040-4039(91)80053-9

Reference yield: 99.1%

1,2-dimethoxynaphthalene (57189-64-7) → 1,2-naphthoquinone (524-42-5)

Guidance literature:

1,2-dimethoxynaphthalene; With lead(IV) tetraacetate; In ethylbenzene; at 46 ℃; for 1.83333h;

With sodium nitrate; zirconium(IV) sulfate; In ethylbenzene; at 56 ℃; for 3.66667h; Temperature;

Reference yield: 95.0%

β-naphthol (135-19-3) → 1,2-naphthoquinone (524-42-5)

Guidance literature:

With 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride; In dichloromethane; at -80 ℃;

DOI:10.1016/S0040-4039(00)99949-0

upstream raw materials:

chloroform

1-bromo-1-nitro-1H-naphthalen-2-one

1,2-Dihydroxynaphthalene

1-chloro-2-naphthol

Downstream raw materials:

1,2,4-triacetyloxynaphthalene

1,2-naphthalenediol diacetate

[1.1']Binaphthyltetrayl-(3.4.3'.4')-tetraacetat

4-(3,4-dioxo-3,4-dihydro-[1]naphthylamino)-benzoic acid

Refernces

• 1、 Yadav, Dhananjay,Shukla, Gaurav,Ansari, Monish A.,Srivastava, Abhijeet,Singh, Maya Shankar. "Chemoselective one-pot access to benzo[e]indole-4,5-diones and naphtho[2,1-b]thiophene-4,5-diones via copper-catalyzed oxidative [3 + 2] annulation of α-oxoketene N,S-acetals/β-ketothioamides with α-/β-naphthols". . p. 5920 - 5931. Retrieved 2018.
• 2、 Nam, Sangkil,Renganathan,Tratnyek, Paul G.. "Substituent effects on azo dye oxidation by the FeIII-EDTA-H2O2 system". . p. 59 - 65. Retrieved 2001.
• 3、 Sebastiano, Roberto,Contiello, Nunzia,Senatore, Stanislao,Righetti, Pier Giorgio,Citterio, Attilio. "Analysis of commercial Acid Black 194 and related dyes by micellar electrokinetic chromatography". . p. 258 - 265. Retrieved 2012.
• 4、 Vaz, Nirmala,Manjunatha,Puttaswamy. "Kinetic and mechanistic studies on the oxidative decolourisation of orange-II dye with alkaline chloramine-T". . p. 363 - 367. Retrieved 2015.
• 5、 Paul, Melanie,Hoffmann, Alexander,Herres-Pawlis, Sonja. "Room temperature stable multitalent: highly reactive and versatile copper guanidine complexes in oxygenation reactions". . p. 249 - 263. Retrieved 2021.
• 6、 Adam, Waldemar,Peters, Eva Maria,Peters, Karl,Prein, Michael,Von Schnering, Hans Georg. "Diastereoselective photooxygenation of chiral naphthyl alcohols: The hydroxy group directing effect in singlet oxygen [4 + 2] cycloaddition to arenes". . p. 6686 - 6690. Retrieved 1995.
• 7、 Shukla, Gaurav,Srivastava, Abhijeet,Yadav, Dhananjay,Singh, Maya Shankar. "Copper-Catalyzed One-Pot Cross-Dehydrogenative Thienannulation: Chemoselective Access to Naphtho[2,1-b]thiophene-4,5-diones and Subsequent Transformation to Benzo[a]thieno[3,2-c]phenazines". . p. 2173 - 2181. Retrieved 2018.
• 8、 Boelke, Andreas,Lork, Enno,Nachtsheim, Boris J.,Sadat, Soleicha. "Pseudocyclic bis-N-heterocycle-stabilized iodanes - synthesis, characterization and applications". supporting information. p. 7434 - 7437. Retrieved 2021/08/03.