2-Methylanthraquinone

2-Methylanthraquinone
Names
Preferred IUPAC name
2-Methylanthracene-9,10-dione
Other names
  • β-Methylanthraquinone
  • Tectoquinone
Identifiers
3D model (JSmol)
2050523
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.399 Edit this at Wikidata
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
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).

2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone, is an organic compound which is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes. It is present in the wood of the teak tree, where it gives the tree resistance to insects.

Synthesis and reactions

The compound is produced by a double electrophilic aromatic substitution reaction of toluene with phthalic anhydride.

Summary eq for synthesis of 2-methylanthraquinone

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.

References

  1. ↑ 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. ↑ "2-Methylanthraquinone". CAS Common Chemistry. Retrieved 5 August 2023.
  3. 1 2 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.
  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. Bibcode:1958Natur.181..721R. doi:10.1038/181721b0. S2CID 4159998.
  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.