Trimesic acid

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Trimesic acid


IUPAC name benzene-1,3,5-tricarboxylic acid
Identifiers
CAS number	554-95-0^Y
PubChem	11138
ChemSpider	10665^Y
EC number	209-077-7
DrugBank	DB08632
ChEBI	CHEBI:46032^Y
ChEMBL	CHEMBL77562^Y
Jmol-3D images	Image 1
SMILES c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O
InChI InChI=1S/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)^Y Key: QMKYBPDZANOJGF-UHFFFAOYSA-N^Y InChI=1/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15) Key: QMKYBPDZANOJGF-UHFFFAOYAC
Properties
Molecular formula	C₉H₆O₆
Molar mass	210.14034
Acidity (pK_a)	3.12, 3.89, 4.70^[1]
Hazards
MSDS	Oxford MSDS
R-phrases	R36 R37 R38
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Trimesic acid, also known as benzene-1,3,5-tricarboxylic acid, is a benzene derivative with three carboxylic acid groups.

Trimesic acid is a planar molecule (and is one of only four benzenecarboxylic acids with that property).^[2]

Trimesic acid can be combined with para-hydroxypyridine to make a water-based gel, stable up to 95 °C.^[3]

Trimesic acid crystallizes from water in a hydrogen-bonded hydrated network with wide unidimensional empty channels.^[4]

References

↑ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
↑ ZORAN MARKOVIĆ, DALIBOR BADJUK and IVAN GUTMAN (2004), Geometry and conformations of benzenecarboxylic acids. J. Serb. Chem. Soc. volume 69 issue 11, pages 877–882 (paper JSCS 3214), UDC 547.584/.585:539.193:54.02
↑ Li Ming Tang and Yu Jiang Wang (2009), Highly stable supramolecular hydrogels formed from 1,3,5-benzenetricarboxylic acid and hydroxyl pyridines. Chinese Chemical Letters volume 20, issue 10, pp. 1259–1262. doi:10.1016/j.cclet.2009.04.030
↑ F.H. Herbstein (1987), Structural Parsimony and Structural Variety Among Inclusion Complexes, Top. Curr. Chem., volume 140, p. 107

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