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 ;
EC Number	209-077-7;
Gmelin Reference	51147
PubChem CID	11138;
UNII	OU36OO5MTN ;
	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
Hazards
Safety data sheet	Oxford MSDS
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	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 an organic compound with the formula C₆H₃(CO₂H)₃. It is one of three isomers of benzenetricarboxylic acid.^[2] A colorless solid, trimesic acid has some commercial value as a precursor to some plasticizers.^[3]

Trimesic acid can be combined with para-hydroxypyridine to make a water-based gel, stable up to 95 °C.^[4]

Trimesic acid crystallizes from water to form a hydrogen-bonded hydrated network with wide unidimensional empty channels.^[5]^[6]

References

↑ "1,3,5-Benzenetricarboxylic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/11138#section=Safety-and-Hazards.
↑ 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). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_249.
↑ 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. 140. pp. 107–139. doi:10.1007/bfb0003838. ISBN 3-540-17307-2.

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[1] "1,3,5-Benzenetricarboxylic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/11138#section=Safety-and-Hazards.

[MARKOVIC-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] Röhrscheid, Freimund (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_249.

[Tang-4] 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.

[5] 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-6] 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.

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Trimesic acid

Topic: Chemistry

See also

References