2-Hydroxy-3-methyl-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Hydroxy-3-methyl-1,4-naphthoquinone
• CAS No.: 483-55-6
• Molecular Formula: C11H8O3
• Molecular Weight: 188.183
• European Community (EC) Number: 207-594-2
• NSC Number: 11897
• UNII: 8R72C50E69
• DSSTox Substance ID: DTXSID80876664
• Nikkaji Number: J2.386.294H,J5.987K
• Wikidata: Q27270921,Q104935743
• Metabolomics Workbench ID: 98753,103760
• ChEMBL ID: CHEMBL158364
• Mol file: 483-55-6.mol

Synonyms:2-hydroxy-3-methyl-1,4-naphthoquinone;phthiocol

Chemical Property of 2-Hydroxy-3-methyl-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 173-174°
• Refractive Index: 1.646
• Boiling Point: 342.655 °C at 760 mmHg
• PKA: 5.21±0.10(Predicted)
• Flash Point: 175.232 °C
• PSA: 54.37000
• Density: 1.389 g/cm³
• LogP: 1.89760
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 188.047344113
• Heavy Atom Count: 14
• Complexity: 327

Purity/Quality:

99.9% ^*data from raw suppliers

2-HYDROXY-3-METHYL-1,4-NAPHTHOQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2C(=O)C1=O)O

Technology Process of 2-Hydroxy-3-methyl-1,4-naphthoquinone

There total 102 articles about 2-Hydroxy-3-methyl-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: 96.0%

2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone (15448-59-6,61840-91-3,82864-14-0,105016-62-4) → phthiocol (483-55-6)

Guidance literature:

With sulfuric acid; silica gel; at 70 ℃; for 0.133333h;

DOI:10.1055/s-2007-985584

Reference yield: 95.0%

1,2,4-triacetoxy-3-methylnaphthalene (604-86-4) + acetic anhydride (108-24-7) → phthiocol (483-55-6)

Guidance literature:

With aluminum oxide; potassium fluoride; oxygen; In methanol; at 25 ℃;

Reference yield: 93.0%

menadione (58-27-5,34524-96-4) → phthiocol (483-55-6)

Guidance literature:

With water; dihydrogen peroxide; sodium carbonate; In methanol; at 100 ℃;

DOI:10.1016/j.tetlet.2017.08.009

upstream raw materials:

2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone

ethanol

2-hydroxynaphtho-1,4-quinone

diacetyl peroxide

Downstream raw materials:

2-methoxy-3-methyl-1,4-naphthoquinone

4-Amino-2-hydroxy-benzoic acid [2-hydroxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazide

3-Hydroxy-4-[(4-iodo-phenyl)-hydrazono]-2-methyl-4H-naphthalen-1-one

4-{N'-[2-Hydroxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid

Refernces

• 1、 Kathawate, Laxmi,Gejji, Shridhar P.,Yeole, Sachin D.,Verma, Prakash L.,Puranik, Vedavati G.,Salunke-Gawali, Sunita. "The first naphthosemiquinone complex of K+ with vitamin K3 analog: Experiment and density functional theory". . p. 56 - 63. Retrieved 2015.
• 2、 Read,G.,Ruiz,V.M.. "-". . p. 368 - 373. Retrieved 1973.
• 3、 Geisler, Heiko,Westermayr, Julia,Cseh, Klaudia,Wenisch, Dominik,Fuchs, Valentin,Harringer, Sophia,Plutzar, Sarah,Gajic, Natalie,Hejl, Michaela,Jakupec, Michael A.,Marquetand, Philipp,Kandioller, Wolfgang. "Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies". . p. 9805 - 9819. Retrieved 2021/06/30.
• 4、 Mészáros, János P.,Geisler, Heiko,Poljarevi?, Jelena M.,Roller, Alexander,Legina, Maria S.,Hejl, Michaela,Jakupec, Michael A.,Keppler, Bernhard K.,Kandioller, Wolfgang,Enyedy, éva A.. "Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations". supporting information. . Retrieved 2019/12/23.