9,10-Anthracenedione,2-methyl

9,10-Anthracenedione,2-methyl
Compound Structure:
Synonyms: 2-Methylanthraquinone;84-54-8;Tectoquinone;2-methylanthracene-9,10-dione;2-Methyl anthraquinone;Techtoquinone;Tectochinon;2-Methyl-9,10-anthraquinone;9,10-Anthracenedione, 2-methyl-;beta-Methylanthraquinone;2-Methylanthra-9,10-quinone
Compound ID: NMPC-508
PubChem ID:

6773

Molecular Formula: C15H10O2
Canonical SMILES: CC1=CC2=C(C=C1)C(=O)C3=CC=CC=C3C2=O
InChIKey: NJWGQARXZDRHCD-UHFFFAOYSA-N
About the compound:

2-Methylanthraquinone is an important organic compound primarily utilized as a precursor in dye production and as an intermediate in pharmaceutical manufacturing. This compound is a methylated version of anthraquinone and typically appears as a nearly colorless solid. The molecular formula of 2-Methylanthraquinone is C15H10O2 with a molecular weight of 222.243 g/mol. It has a density of 1.365 g/cm³ and melts at 177°C[1]. The production of 2-Methylanthraquinone generally involves the reaction between phthalic anhydride and toluene. It can undergo additional reactions such as chlorination and nitration, producing derivatives that serve various industrial purposes. Additionally, oxidizing the methyl group yields anthraquinone-2-carboxylic acid[]. In practical applications, 2-Methylanthraquinone is employed in the textile and pharmaceutical sectors. It is crucial in synthesizing anthracycline antibiotics, vital for cancer therapy. It is also used in making smog dyes, noted for their durability and resistance to fading[2]. Handling 2-Methylanthraquinone safely is paramount, as exposure can occur via inhalation, skin contact, or ingestion. Implementing proper safety measures and personal protective equipment is essential to mitigate health risks and ensure safety for individuals and the environment[3].In addition to its natural occurrence, 2-methylanthraquinone serves as a crucial precursor to numerous dyes. Its significance extends to the wood of the teak tree, where its presence imparts resistance to insects. As an off-white solid, this compound holds practical importance in industries related to dye production, showcasing its versatile applications beyond its natural origins. The exploration of 2-methylanthraquinone sheds light on both its natural roles in organisms and its synthetic applications in various industrial processes.

References 

1. Kingsford-Adaboh, R., & Kashino, S. (1995). Disordered Structure of 2-Methylanthraquinone. Acta Crystallographica Section C, 51(10), 2094-2096. https://doi.org/10.1107/S0108270195003842

2. Rudman, P., Da Costa, E. W. B., Gay, F. J., & Wetherly, A. H. (1958). Relationship of tectoquinone to durability in Tectona grandis. Nature, 181(4610), 721-722. https://doi.org/10.1038/181721b0

3. Fieser, L. F. (1925). p-Toluyl-o-Benzoic Acid. Organic Syntheses, 4, 73. https://doi.org/10.15227/orgsyn.004.0073

4. Fieser, L. F. (1925). β-Methylanthraquinone. Organic Syntheses, 4, 43. https://doi.org/10.15227/orgsyn.004.0043

5. Bien, H.-S., Stawitz, J., & Wunderlich, K. (2000). Anthraquinone Dyes and Intermediates. Ullmann's Encyclopedia of Industrial Chemistry. https://doi.org/10.1002/14356007.a02_355.

GHS Hazard Statements

H317 (33.33%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H400 (66.67%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (66.67%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

222.24 g/mol

XLogP3

3.9

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

0

Exact Mass

222.068079557 g/mol

Monoisotopic Mass

222.068079557 g/mol

Topological Polar Surface Area

34.1Ų

Heavy Atom Count

17

Formal Charge

0

Complexity

347

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem

Source Species: Tectona grandis
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