2-Methylanthraquinone

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]

2-Methylanthraquinone
Names
Preferred IUPAC name
2-Methylanthracene-9,10-dione
Other names
  • β-Methylanthraquinone
  • Tectoquinone
Identifiers
3D model (JSmol)
3DMet
2050523
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.399
EC Number
  • 201-539-6
1607902
KEGG
UNII
  • InChI=1S/C15H10O2/c1-9-6-7-12-13(8-9)15(17)11-5-3-2-4-10(11)14(12)16/h2-8H,1H3
    Key: NJWGQARXZDRHCD-UHFFFAOYSA-N
  • Cc1ccc2c(c1)C(=O)c3ccccc3C2=O
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:
GHS07: Exclamation markGHS09: Environmental hazard
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).
Infobox references

Synthesis and reactions

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]

Summary eq for synthesis of 2-methylanthraquinone.

References
  1. Kingsford-Adaboh, R.; Kashino, S. (1995). "Disordered Structure of 2-Methylanthraquinone". Acta Crystallographica Section C. 51 (10): 2094–2096. doi:10.1107/S0108270195003842.
  2. "2-Methylanthraquinone". CAS Common Chemistry. Retrieved 5 August 2023.
  3. 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 3527306730.
  4. 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. doi:10.1038/181721b0.
  5. L. F. Fieser (1925). "p-Toluyl-o-Benzoic Acid". Organic Syntheses. 4: 73. doi:10.15227/orgsyn.004.0073.
  6. L. F. Fieser (1925). "β-Methylanthraquinone". Organic Syntheses. 4: 43. doi:10.15227/orgsyn.004.0043.
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