Mesitol

Mesitol
Names
	Preferred IUPAC name 2,4,6-Trimethylphenol
	Other names Hydroxymesitylene; Mesityl alcohol
Identifiers
CAS Number	527-60-6;
3D model (JSmol)	Interactive image;
ChemSpider	10248;
ECHA InfoCard	100.007.655
EC Number	208-419-2;
PubChem CID	10698;
UNII	FPZ32614N6;
CompTox Dashboard (EPA)	DTXSID7022049 ;
	InChI InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3 Key: BPRYUXCVCCNUFE-UHFFFAOYSA-N;
	SMILES Cc1cc(c(c(c1)C)O)C;
Properties
Chemical formula	C9H12O
Molar mass	136.194 g·mol−1
Appearance	white solid
Melting point	70–72 °C (158–162 °F; 343–345 K)
Boiling point	220 °C (428 °F; 493 K)
Solubility in water	1.01 g/l
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H411
Precautionary statements	P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Mesitol (2,4,6-trimethylphenol) is an organic compound with the formula (CH₃)₃C₆H₂OH. It is one of several isomers of trimethylphenol. The name and structure of mesitol derives from the combination of mesitylene and phenol.

Synthesis

Mesitol is the main product from the methylation of phenol with methanol in the presence of a solid acid.^[2]

It can also be obtained by reaction of mesitylene with peroxymonophosphoric acid:^[3]

An alternative route involves palladium-catalyzed reaction of bromomesitylene with potassium hydroxide.^[4]

References

^ ^a ^b "2,4,6-Trimethylphenol". Sigma-Aldrich.
^ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
^ Ogata, Yoshiro; Sawaki, Yasuhiko; Tomizawa, Kohtaro; Ohno, Takashi (1981). "Aromatic hydroxylation with peroxymonophosphoric acid". Tetrahedron. 37 (8): 1485. doi:10.1016/S0040-4020(01)92087-3.
^ Anderson, Kevin W.; Ikawa, Takashi; Tundel, Rachel E.; Buchwald, Stephen L. (2006). "The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans". Journal of the American Chemical Society. 128 (33): 10694–10695. doi:10.1021/ja0639719. PMID 16910660.

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[SA-1] "2,4,6-Trimethylphenol". Sigma-Aldrich.

[2] Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.

[3] Ogata, Yoshiro; Sawaki, Yasuhiko; Tomizawa, Kohtaro; Ohno, Takashi (1981). "Aromatic hydroxylation with peroxymonophosphoric acid". Tetrahedron. 37 (8): 1485. doi:10.1016/S0040-4020(01)92087-3.

[4] Anderson, Kevin W.; Ikawa, Takashi; Tundel, Rachel E.; Buchwald, Stephen L. (2006). "The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans". Journal of the American Chemical Society. 128 (33): 10694–10695. doi:10.1021/ja0639719. PMID 16910660.

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