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Revision as of 14:10, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 458204211 of page Trimesic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 16:55, 22 January 2024 edit WikiCleanerBot (talk | contribs)Bots928,113 editsm v2.05b - Bot T5 CW#16 - Fix errors for CW project (Unicode control characters)Tag: WPCleaner
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
		⚫	| verifiedrevid = 470615012
	| Verifiedfields = changed
		⚫	| ImageFile = Trimesic acid.svg
⚫	| verifiedrevid = 419117422
		⚫	| ImageSize = 180px
⚫	| ImageFile = Trimesic acid.svg
		⚫	| ImageName = Skeletal formula
⚫	| ImageSize = 180px
		⚫	| ImageFile1 = Trimesic-acid-3D-balls.png
⚫	| ImageName = Skeletal formula
		⚫	| ImageName1 = Ball-and-stick model
⚫	| ImageFile1 = Trimesic-acid-3D-balls.png
		⚫	| PIN = Benzene-1,3,5-tricarboxylic acid
	| ImageSize1 = 200px
		⚫	| OtherNames =
⚫	| ImageName1 = Ball-and-stick model
⚫	| IUPACName = benzene-1,3,5-tricarboxylic acid
⚫	| OtherNames =
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| 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		| 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)		| 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		| InChIKey = QMKYBPDZANOJGF-UHFFFAOYAC
⚫	| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫	| ChEMBL = 77562
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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)		| 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_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QMKYBPDZANOJGF-UHFFFAOYSA-N		| StdInChIKey = QMKYBPDZANOJGF-UHFFFAOYSA-N
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| CASNo=554-95-0
⚫	| EINECS = 209-077-7
⚫	| PubChem=11138
⚫	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
⚫	| DrugBank = DB08632
⚫	| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫	| ChEBI = 46032
	| SMILES = c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O		| SMILES = c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>9</sub>H<sub>6</sub>O<sub>6</sub>		| Formula=C<sub>9</sub>H<sub>6</sub>O<sub>6</sub>
	| MolarMass=210.14034		| MolarMass=210.14034
	| Appearance=		| Appearance=
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=
	| BoilingPt=		| BoilingPt=
	| pKa=3.12, 3.89, 4.70<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref>		| pKa=3.12, 3.89, 4.70<ref>{{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= ] |location= New York |year= 1955 |doi= 10.1016/B978-1-4832-3166-2.50018-4 }}</ref>
	| Solubility=		| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| Hazards_ref=<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}}</ref>
	| RPhrases = {{ R36}} {{R37}} {{R38}}
			| GHSPictograms = {{GHS07}}
	| Autoignition=
			| 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 ] with the formula C<sub>6</sub>H<sub>3</sub>(CO<sub>2</sub>H)<sub>3</sub>. It is one of three isomers of ].<ref name="MARKOVIC">{{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 }}</ref> A colorless solid, trimesic acid has some commercial value as a precursor to some ]s.<ref>{{Ullmann |doi=10.1002/14356007.a05_249|title=Carboxylic Acids, Aromatic|year=2000|last1=Röhrscheid|first1=Freimund}}</ref>
			Trimesic acid can be combined with ] to make a water-based gel, stable up to 95 °C.<ref name="Tang">{{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 }}</ref>
			Trimesic acid crystallizes from water to form a ] with wide unidimensional empty channels.<ref>{{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=] |volume=1 |issue=1 |pages=77–87 |doi=10.1021/accountsmr.0c00019}}</ref><ref name="Herbstein">{{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 }}</ref>
			==See also==
			* ] (1,2,4-benzenetricarboxylic acid)
			* ] (1,2,3-benzenetricarboxylic acid)
			==References==
			{{Reflist}}
			{{DEFAULTSORT:Trimesic Acid}}
			]
			]
			]
			{{organic-compound-stub}}