Trimesic acid

{{chembox

| verifiedrevid = 470615012

| ImageFile = Trimesic acid.svg

| ImageSize = 180px

| ImageName = Skeletal formula

| ImageFile1 = Trimesic-acid-3D-balls.png

| ImageName1 = Ball-and-stick model

| PIN = Benzene-1,3,5-tricarboxylic acid

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=554-95-0

| Abbreviations = TMA

| Beilstein = 2053080

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 46032

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 77562

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10665

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB08632

| EC_number = 209-077-7

| Gmelin = 51147

| PubChem=11138

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = OU36OO5MTN

| 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)

| InChIKey = QMKYBPDZANOJGF-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QMKYBPDZANOJGF-UHFFFAOYSA-N

| SMILES = c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O

}}

|Section2={{Chembox Properties

| Formula=C₉H₆O₆

| MolarMass=210.14034

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| pKa=3.12, 3.89, 4.70{{cite book |last1= Brown |first1= H.C. |author1-link= Herbert C. Brown |last2= McDaniel |first2= D.H. |last3= Häfliger |first3= O. |chapter= Chapter 14—Dissociation Constants |editor1-last= Braude |editor1-first= E.A. |editor2-last= Nachod |editor2-first= F.C. |title= Determination of Organic Structures by Physical Methods |publisher= Academic Press |location= New York |year= 1955 |doi= 10.1016/B978-1-4832-3166-2.50018-4 }}

| Solubility=

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/TR/trimesic_acid.html Oxford MSDS]

| Hazards_ref={{cite web |title=1,3,5-Benzenetricarboxylic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/11138#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

| AutoignitionPt =

}}

}}

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.{{cite journal |first1= Zoran |last1= Marković |first2= Dalibor |last2= Badjuk |first3= Ivan |last3= Gutman |year= 2004 |title= Geometry and Conformations of Benzenecarboxylic Acids |journal= J. Serb. Chem. Soc. |volume= 69 |issue= 11 |pages= 877–882 |doi= 10.2298/JSC0411877M |doi-access= free }} A colorless solid, trimesic acid has some commercial value as a precursor to some plasticizers.{{Ullmann |doi=10.1002/14356007.a05_249|title=Carboxylic Acids, Aromatic|year=2000|last1=Röhrscheid|first1=Freimund}}

Trimesic acid can be combined with para-hydroxypyridine to make a water-based gel, stable up to 95 °C.{{cite journal |first1= Li Ming |last1= Tang |first2= Yu Jiang |last2= Wang |year= 2009 |title= Highly Stable Supramolecular Hydrogels Formed from 1,3,5-Benzenetricarboxylic Acid and Hydroxyl Pyridines |journal= Chinese Chemical Letters |volume= 20 |issue= 10 |pages= 1259–1262 |doi= 10.1016/j.cclet.2009.04.030 }}

Trimesic acid crystallizes from water to form a hydrogen-bonded hydrated network with wide unidimensional empty channels.{{cite journal |last1=Li |first1=Penghao |last2=Ryder |first2=Matthew R. |last3=Stoddart |first3=J. Fraser |year=2020 |title=Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials |journal=Accounts of Materials Research |volume=1 |issue=1 |pages=77–87 |doi=10.1021/accountsmr.0c00019}}{{cite book |first= Frank H. |last= Herbstein |year= 1987 |chapter= 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") |title= Top. Curr. Chem. |series= Topics in Current Chemistry |volume= 140 |pages= 107–139 |doi= 10.1007/bfb0003838 |isbn= 3-540-17307-2 }}