2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

which is a methylated derivative of

anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic hydrocarbon, aromatic organic compound with formula . Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein th ...

. An off-white solid, it is an important precursor to many dyes. It is present in the wood of the

teak Teak (''Tectona grandis'') is a tropical hardwood tree species in the family Lamiaceae. It is a large, deciduous tree that occurs in mixed hardwood forests. ''Tectona grandis'' has small, fragrant white flowers arranged in dense clusters (panic ...

tree, where it gives the tree resistance to insects.

Synthesis and reactions

The compound is produced by a double

electrophilic aromatic substitution Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic ring, aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitut ...

reaction of

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

with

phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...

. :

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.{{cite book, doi=10.1002/14356007.a02_355, chapter=Anthraquinone Dyes and Intermediates, title=Ullmann's Encyclopedia of Industrial Chemistry, year=2000, last1=Bien, first1=Hans-Samuel, last2=Stawitz, first2=Josef, last3=Wunderlich, first3=Klaus, isbn=3-527-30673-0

Synthesis and reactions

References