Trimesic acid

Last updated
Trimesic acid
Trimesic acid.svg
Trimesic-acid-3D-balls.png
Names
Preferred IUPAC name
Benzene-1,3,5-tricarboxylic acid
Identifiers
3D model (JSmol)
AbbreviationsTMA
2053080
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.253 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-077-7
51147
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: QMKYBPDZANOJGF-UHFFFAOYSA-N Yes check.svgY
  • 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
  • c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O
Properties
C9H6O6
Molar mass 210.14034
Acidity (pKa)3.12, 3.89, 4.70 [1]
Hazards [2]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

See also

Related Research Articles

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3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

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COOOH
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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.