2-Methylanthraquinone
Appearance
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Names | |
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Preferred IUPAC name
2-Methylanthracene-9,10-dione | |
Other names
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Identifiers | |
3D model (JSmol)
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3DMet | |
2050523 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.399 |
EC Number |
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1607902 | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H10O2 | |
Molar mass | 222.243 g·mol−1 |
Appearance | almost colorless |
Density | 1.365 g/cm3[1] |
Melting point | 177 °C (351 °F; 450 K) |
Hazards | |
GHS labelling: | |
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Warning | |
H317, H410 | |
P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone,[2] is an organic compound which is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes.[3] It is present in the wood of the teak tree, where it gives the tree resistance to insects.[4]
Synthesis and reactions
[edit]The compound is produced by the reaction of phthalic anhydride and toluene.[5][6] It can be chlorinated to give 1-chloro-2-methylanthraquinone. Nitration gives 1-nitro-2-methylanthraquinone, which can be reduced to 1-amino-2-methyl derivative. Oxidation of the methyl group gives anthraquinone-2-carboxylic acid.[3]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/e/e9/2-MeAnthraquinone.svg/220px-2-MeAnthraquinone.svg.png)
References
[edit]- ^ Kingsford-Adaboh, R.; Kashino, S. (1995). "Disordered Structure of 2-Methylanthraquinone". Acta Crystallographica Section C. 51 (10): 2094–2096. Bibcode:1995AcCrC..51.2094K. doi:10.1107/S0108270195003842.
- ^ "2-Methylanthraquinone". CAS Common Chemistry. Retrieved 5 August 2023.
- ^ a b Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_355. ISBN 3-527-30673-0.
- ^ Rudman, P.; Da Costa, E. W. B.; Gay, F. J.; Wetherly, A. H. (8 March 1958). "Relationship of tectoquinone to durability in Tectona grandis". Nature. 181 (4610): 721–722. Bibcode:1958Natur.181..721R. doi:10.1038/181721b0. S2CID 4159998.
- ^ L. F. Fieser (1925). "p-Toluyl-o-Benzoic Acid". Organic Syntheses. 4: 73. doi:10.15227/orgsyn.004.0073.
- ^ L. F. Fieser (1925). "β-Methylanthraquinone". Organic Syntheses. 4: 43. doi:10.15227/orgsyn.004.0043.