1-Hydroxy-2-methylanthraquinone

Base Information

• Chemical Name: 1-Hydroxy-2-methylanthraquinone
• CAS No.: 6268-09-3
• Molecular Formula: C15H10 O3
• Molecular Weight: 238.243
• NSC Number: 37131
• DSSTox Substance ID: DTXSID80211733
• Nikkaji Number: J269.608H
• Wikidata: Q27137873
• Metabolomics Workbench ID: 133902
• ChEMBL ID: CHEMBL42302
• Mol file: 6268-09-3.mol

Synonyms:1-hydroxy-2-methylanthraquinone

Chemical Property of 1-Hydroxy-2-methylanthraquinone

Chemical Property:

• Vapor Pressure: 1.61E-08mmHg at 25°C
• Melting Point: 184-185℃
• Boiling Point: 444.6°C at 760 mmHg
• PKA: 7.45±0.20(Predicted)
• Flash Point: 236.8°C
• Density: 1.371g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 238.062994177
• Heavy Atom Count: 18
• Complexity: 376

Purity/Quality:

99%+, ^*data from raw suppliers

1-Hydroxy-2-Methylanthraquinone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C=C1)C(=O)C3=CC=CC=C3C2=O)O
• Uses: 1-Hydroxy-2-methyl-9,10-anthraquinone can be used to treat osteoporosis and prophylaxis of nervous system disease.

Technology Process of 1-Hydroxy-2-methylanthraquinone

There total 10 articles about 1-Hydroxy-2-methylanthraquinone 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: 82.4%

1-Cyclopropylmethoxy-2-methyl-anthraquinone (171816-10-7) → 1-hydroxy-2-methyl-anthraquinone (6268-09-3) + Cyclopropanecarboxaldehyde (1489-69-6)

Guidance literature:

In methanol; for 2h; Mechanism; Product distribution; Irradiation;

DOI:10.1021/ja962633c

Reference yield: 80.0%

1-<<3-(o-Nitrophenyl)propyl>oxy>-2-methyl-9,10-anthraquinone (114446-46-7) → 1-hydroxy-2-methyl-anthraquinone (6268-09-3) + o-nitrohydrocinnamaldehyde (133473-26-4)

Guidance literature:

In methanol; for 15h; Irradiation;

DOI:10.1021/jo00247a052

Reference yield: 37.0%

phthalic anhydride (85-44-9) + ortho-cresol (95-48-7,77504-84-8) → 1-hydroxy-2-methyl-anthraquinone (6268-09-3)

Guidance literature:

With aluminum (III) chloride; sodium chloride; at 150 - 170 ℃; for 0.75h;

DOI:10.2174/1570180815666180607085102

upstream raw materials:

phthalic anhydride

ortho-cresol

trimethyl(phenyl)stannane

Trifluoro-methanesulfonic acid 1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl ester

Downstream raw materials:

1-<(p-chlorobenzyl)oxy>-2-methyl-9,10-anthraquinone

1-<(p-methylbenzyl)oxy>-2-methyl-9,10-anthraquinone

1-<(p-cyanobenzyl)oxy>-2-methyl-9,10-anthraquinone

1-<(p-nitrobenzyl)oxy>-2-methyl-9,10-anthraquinone

Refernces

• 1、 Smart, Robert P.,Peelen, Timothy J.,Blankespoor, Ronald L.,Ward, Donald L.. "Short-lived 1,5-biradicals formed from triplet 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones". . p. 461 - 465. Retrieved 2007/10/03.
• 2、 Tamayo, Nuria,Echavarren, Antonio M.,Paredes, M. Carmen,Farina, Francisco,Noheda, Pedro. "Synthesis of anthraquinone derivatives by palladium-catalyzed coupling of triflates with stannanes". . p. 5189 - 5192. Retrieved 2007/10/02.