Trimesic acid

Trimesic acid
Names
	IUPAC name benzene-1,3,5-tricarboxylic acid
Identifiers
CAS Number	554-95-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46032 ;
ChEMBL	ChEMBL77562 ;
ChemSpider	10665 ;
DrugBank	DB08632 ;
ECHA InfoCard	100.008.253
EC Number	209-077-7
PubChem CID	11138;
	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) Key: QMKYBPDZANOJGF-UHFFFAOYSA-N ; 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;
	SMILES c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O;
Properties
Chemical formula	C9H6O6
Molar mass	210.14034
Acidity (pKa)	3.12, 3.89, 4.70[1]
Hazards
Safety data sheet	Oxford MSDS
R-phrases (outdated)	R36 R37 R38
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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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