Trimesic acid

Trimesic acid
Names
	Preferred IUPAC name Benzene-1,3,5-tricarboxylic acid
Identifiers
CAS Number	554-95-0 ;
3D model (JSmol)	Interactive image;
Abbreviations	TMA
Beilstein Reference	2053080
ChEBI	CHEBI:46032 ;
ChEMBL	ChEMBL77562 ;
ChemSpider	10665 ;
DrugBank	DB08632 ;
ECHA InfoCard	100.008.253
EC Number	209-077-7;
Gmelin Reference	51147
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
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302 P352, P304 P340, P305 P351 P338, P312, P321, P332 P313, P337 P313, P362, P403 P233, P405, P501
Safety data sheet (SDS)	Oxford MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trimesic acid, also known as benzene-1,3,5-tricarboxylic acid, is an organic compound with the formula C₆H₃(CO₂H)₃. It is one of three isomers of benzenetricarboxylic acid.^[3] A colorless solid, trimesic acid has some commercial value as a precursor to some plasticizers.^[4]

Trimesic acid can be combined with para-hydroxypyridine to make a water-based gel, stable up to 95 °C.^[5]

Trimesic acid crystallizes from water to form a hydrogen-bonded hydrated network with wide unidimensional empty channels.^[6]^[7]

References

^ 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.
^ "1,3,5-Benzenetricarboxylic acid". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ Röhrscheid, Freimund (2000). "Carboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_249. ISBN 978-3527306732.
^ 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.
^ Li, Penghao; Ryder, Matthew R.; Stoddart, J. Fraser (2020). "Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials". Accounts of Materials Research. 1 (1): 77–87. doi:10.1021/accountsmr.0c00019.
^ 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. Vol. 140. pp. 107–139. doi:10.1007/bfb0003838. ISBN 3-540-17307-2.

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[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] "1,3,5-Benzenetricarboxylic acid". pubchem.ncbi.nlm.nih.gov.

[MARKOVIC-3] 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.

[4] Röhrscheid, Freimund (2000). "Carboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_249. ISBN 978-3527306732.

[Tang-5] 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.

[6] Li, Penghao; Ryder, Matthew R.; Stoddart, J. Fraser (2020). "Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials". Accounts of Materials Research. 1 (1): 77–87. doi:10.1021/accountsmr.0c00019.

[Herbstein-7] 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. Vol. 140. pp. 107–139. doi:10.1007/bfb0003838. ISBN 3-540-17307-2.

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See also

References