1,4-Naphthoquinone

Base Information

• Chemical Name: 1,4-Naphthoquinone
• CAS No.: 130-15-4
• Molecular Formula: C10H6O2
• Molecular Weight: 158.156
• Hs Code.: 29146910
• European Community (EC) Number: 204-977-6
• ICSC Number: 1547
• NSC Number: 9583
• UN Number: 2811,3077
• UNII: RBF5ZU7R7K
• DSSTox Substance ID: DTXSID5040704
• Nikkaji Number: J5.430E
• Wikipedia: 1,4-Naphthoquinone
• Wikidata: Q161542
• Pharos Ligand ID: KANYT64HS4DX
• Metabolomics Workbench ID: 51312
• ChEMBL ID: CHEMBL55934
• Mol file: 130-15-4.mol

Synonyms:1,4-naphthoquinone;Succivil

Chemical Property of 1,4-Naphthoquinone

Chemical Property:

• Appearance/Colour: Yellow needles or brownish green powder with an odor of benzoquinone
• Vapor Pressure: 0.00131mmHg at 25°C
• Melting Point: 119-122 °C(lit.)
• Refractive Index: 1.617
• Boiling Point: 297.935 °C at 760 mmHg
• Flash Point: 111.219 °C
• PSA: 34.14000
• Density: 1.29 g/cm³
• LogP: 1.62180
• Storage Temp.: Store below +30°C.
• Solubility.: 0.09g/l
• Water Solubility.: insoluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 158.036779430
• Heavy Atom Count: 12
• Complexity: 227
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

1,4-Naphthoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N,T,C,F
• Statements: 25-26-36/37/38-43-50-34-11
• Safety Statements: 26-36/37-45-61-38-36/37/39-28A-24-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C2C(=O)C=CC(=O)C2=C1
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes and skin. The substance is irritating to the respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Description: 1,4-Naphthoquinone (1,4-NQ) is a derivative of naphthalene, characterized by its quinone structure. 1,4-Naphthoquinone has been used in industrial processes since the early 1980s.
• Uses: 1,4-Naphthoquinone is primarily used in industrial processes as a precursor to anthraquinone in the synthesis of dyes and other industrial products. It also exhibits potential pharmacological activity, including inhibition of human monoamine oxidase and anti-inflammatory properties.
• References: [1] Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study; DOI 10.3390/molecules28186644; [2] Metal-Free C–H Sulfamidation of 1,4-Naphthoquinone in Water; DOI 10.1021/acs.joc.3c01409; [3] A review of the genotoxic potential of 1,4-naphthoquinone; DOI 10.1016/j.mrgentox.2018.07.004; [3] Evaluation of 1,4-naphthoquinone derivatives as antibacterial agents: activity and mechanistic studies; DOI 10.1007/s11783-023-1631-2; [4] 1,4-Naphthoquinone Is a Potent Inhibitor of IRAK1 Kinases and the Production of Inflammatory Cytokines in THP-1 Differentiated Macrophages; DOI 10.1021/acsomega.1c03081

Technology Process of 1,4-Naphthoquinone

There total 241 articles about 1,4-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: 78.0%

4-methoxynaphth-1-ol (84-85-5) → benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + [1,4]naphthoquinone (130-15-4)

Guidance literature:

With oxone; In water; acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.5b00292

Reference yield: 72.0%

N-1-naphthalenyl-benzamide (634-42-4) → benzamide (55-21-0,27208-38-4) + [1,4]naphthoquinone (130-15-4)

Guidance literature:

With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; at 25 ℃; for 8h; regioselective reaction;

DOI:10.1021/acs.joc.7b02880

Reference yield: 52.0%

tetralin (119-64-2) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + [1,4]naphthoquinone (130-15-4)

Guidance literature:

With sodium ortho-iodobenzenesulfonate; Oxone; tetra(n-butyl)ammonium hydrogensulfate; In acetonitrile; at 60 ℃; for 4h;

DOI:10.1039/c0ob00722f

upstream raw materials:

diazomethane

phthalic anhydride

naphthalene

1,4-Dihydroxynaphthalene

Downstream raw materials:

2-chloroanthracene-9,10-dione

12-phenylnaphtho<2,3-b>indolizine-6,11-dione

4,9-dioxo-4,9-dihydro-1⁽²⁾H-benz[f]indazole-3-carboxylic acid ethyl ester

2-[2]furyl-5-hydroxy-naphtho[1,2-b]furan-3-carboxylic acid ethyl ester

Refernces

• 1、 Duchstein. "Co-salen - a metal complex generating singlet oxygen (1O2)". . p. 177 - 180. Retrieved 1985.
• 2、 Ponduru, Tharun T.,Qiu, Changling,Mao, James X.,Leghissa, Allegra,Smuts, Jonathan,Schug, Kevin A.,Dias, H. V. Rasika. "Copper(i)-based oxidation of polycyclic aromatic hydrocarbons and product elucidation using vacuum ultraviolet spectroscopy and theoretical spectral calculations". . p. 19442 - 19449. Retrieved 2018.
• 3、 Griffiths et al.. "". . p. 676. Retrieved 1976.
• 4、 Wienhoefer, Gerrit,Schroeder, Kristin,Moeller, Konstanze,Junge, Kathrin,Beller, Matthias. "A novel process for selective Ruthenium-Catalyzed oxidation of naphthalenes and phenols". . p. 1615 - 1620. Retrieved 2010.
• 5、 De Oliveira, Kleber T.,Miller, L. Zane,McQuade, D. Tyler. "Exploiting photooxygenations mediated by porphyrinoid photocatalysts under continuous flow conditions". . p. 12717 - 12725. Retrieved 2016.
• 6、 Yamaguchi, Satoru,Inoue, Masami,Enomoto, Saburo. "The Oxidation of Methylbenzenes and Naphthalenes to Quinones with H2O2 in the Presence of Palladium Catalyst". . p. 2881 - 2884. Retrieved 1986.
• 7、 Deleersnyder, Karen,Schaltin, Stijn,Fransaer, Jan,Binnemans, Koen,Parac-Vogt, Tatjana N.. "Ceric ammonium nitrate (CAN) as oxidizing or nitrating reagent for organic reactions in ionic liquids". . p. 4582 - 4586. Retrieved 2009.
• 8、 Pantaine, Lo?c,Coeffard, Vincent,Moreau, Xavier,Greck, Christine. "One-pot enantioselective synthesis of 1,4-naphthoquinone-derived polycycles through oxidative dearomatization and aminocatalysis". . p. 2005 - 2011. Retrieved 2015.
• 9、 Grissom, Janet Wisniewski,Gunawardena, Gamini U.. "Intramolecular Reaction Of Nitroxide Radicals With Biradical Intermediates Generated From Aromatic Enediynes". . p. 4951 - 4954. Retrieved 1995.
• 10、 Larson, Richard A.,Garrison, Wendy J.,Marley, Karen A.. "Preparation and Photoisomerization of 2-Formylcinnamaldehyde in Solution". . p. 3987 - 3990. Retrieved 1986.