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[edit]

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[edit]

^ ^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 (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.
^ 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 (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

[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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