2-Methylanthraquinone

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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[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).
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Synthesis and reactions

The compound is produced by a double electrophilic aromatic substitution reaction of toluene with phthalic anhydride.[5][6]

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.[3]

References

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