Trimesic acid

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

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
UNII	OU36OO5MTN
CompTox Dashboard (EPA)	DTXSID8021488
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R-phrases (outdated)	R36 R37 R38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 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]

See also

• Trimellitic acid

References

1. Brown, H.C.; McDaniel, D.H.; Häfliger, O. (1955). "Chapter 14—Dissociation Constants". In Braude, E.A.; Nachod, F.C. (eds.). Determination of Organic Structures by Physical Methods. New York: Academic Press. doi:10.1016/B978-1-4832-3166-2.50018-4.
2. Marković, Zoran; Badjuk, Dalibor; Gutman, Ivan (2004). "Geometry and conformations of benzenecarboxylic acids". J. Serb. Chem. Soc. 69 (11): 877–882. doi:10.2298/JSC0411877M.
3. Tang, Li Ming; Wang, Yu Jiang (2009). "Highly stable supramolecular hydrogels formed from 1,3,5-benzenetricarboxylic acid and hydroxyl pyridines". Chinese Chemical Letters. 20 (10): 1259–1262. doi:10.1016/j.cclet.2009.04.030.
4. Herbstein, Frank H. (1987). "Structural Parsimony and Structural Variety Among Inclusion Complexes (with particular reference to the inclusion compounds of trimesic acid, N-(p-tolyl)-tetrachlorophthalimide, and the heilbron "complexes")". Top. Curr. Chem. Topics in Current Chemistry. 140. pp. 107–139. doi:10.1007/bfb0003838. ISBN 3-540-17307-2.