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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Names


Preferred IUPAC name Benzene-1,3,5-tricarboxylic acid
Identifiers
CAS Number	554-95-0^Y
3D model (JSmol)	Interactive image
Abbreviations	TMA
Beilstein Reference	2053080
ChEBI	CHEBI:46032^Y
ChEMBL	ChEMBL77562^Y
ChemSpider	10665^Y
DrugBank	DB08632^Y
ECHA InfoCard	100.008.253
EC Number	209-077-7
Gmelin Reference	51147
PubChem CID	11138
UNII	OU36OO5MTN^Y
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)^Y Key: QMKYBPDZANOJGF-UHFFFAOYSA-N^Y 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 (pK_a)	3.12, 3.89, 4.70^[1]
Hazards^[2]
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). Y verify (what is ^YN ?) Infobox references

Trimesic acid

See also

References

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