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Trimesic acid

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Trimesic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Benzene-1,3,5-tricarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TMA
Beilstein Reference 2053080
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.253 Edit this at Wikidata
EC Number
  • 209-077-7
Gmelin Reference 51147
PubChem CID
UNII
CompTox Dashboard (EPA)
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 GHS07: Exclamation mark
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. A colorless solid, trimesic acid has some commercial value as a precursor to some plasticizers.

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

Trimesic acid crystallizes from water to form a hydrogen-bonded hydrated network with wide unidimensional empty channels.

See also

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