2-Methylanthraquinone

2-Methylanthraquinone
Names
	Preferred IUPAC name 2-Methylanthracene-9,10-dione
	Other names β-Methylanthraquinone; Tectoquinone;
Identifiers
CAS Number	84-54-8;
3D model (JSmol)	Interactive image;
3DMet	B03899;
Beilstein Reference	2050523
ChEBI	CHEBI:9427;
ChEMBL	ChEMBL21745;
ChemSpider	6515;
ECHA InfoCard	100.001.399
EC Number	201-539-6;
Gmelin Reference	1607902
KEGG	C10405;
PubChem CID	6773;
UNII	Q9P233HWAJ;
CompTox Dashboard (EPA)	DTXSID5041439;
	InChI 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;
	SMILES Cc1ccc2c(c1)C(=O)c3ccccc3C2=O;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H317, H410
Precautionary statements	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

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

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

^ 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.

[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.

[Ullmann-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 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.

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