Dinicotinic acid
{{Chembox
|ImageFile = 3,5-Pyridine Dicarboxylic Acid V.2.svg
|ImageSize = 180px
|ImageFile1 = 3,5-pyridinedicarboxylic_acid.jpg
|ImageSize1 = 150px
|PIN = Pyridine-3,5-dicarboxylic acid
|OtherNames = 3,5-Pyridinedicarboxylic acid
|Section1 = {{Chembox Identifiers
|CASNo = 499-81-0
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = N5NMH4PZ3D
|PubChem = 10366
|ChemSpiderID = 9939
|EC_number = 207-893-8
|Beilstein = 131640
|Gmelin = 279307
|ChEBI = 46875
|ChEMBL = 446761
|SMILES = C1=C(C=NC=C1C(=O)O)C(=O)O
|StdInChI=1S/C7H5NO4/c9-6(10)4-1-5(7(11)12)3-8-2-4/h1-3H,(H,9,10)(H,11,12)
|StdInChIKey = MPFLRYZEEAQMLQ-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
|C=7|H=5|N=1|O=4
}}
|Section3 = {{Chembox Structure
|CrystalStruct = monoclinic
|SpaceGroup = P21/c, No. 14
|LattConst_a = 9.702 Å
|LattConst_b = 11.153 Å
|LattConst_c = 6.587 Å
|LattConst_beta = 107.80
|UnitCellFormulas = 4
}}
|Section4 = {{Chembox Hazards
|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}}
}}
}}
Dinicotinic acid (pyridine-3,5-dicarboxylic acid) is a heterocyclic organic compound, more precisely a heteroaromatic. It is one of many pyridinedicarboxylic acids and consists of a pyridine ring carrying to carboxy groups in the 3- and 5-positions.
Preparation and properties
Dinicotinic acid can be formed by heating pyridine-2,3,5,6-tetracarboxylic acid or carbodinicotinic acid (pyridine-2,3,5-tricarboxylic acid).{{Cite journal |last1=Meyer |first1=Hans |last2=Tropsch |first2=Hans |date=1914 |title=Über Dinicotinsäure und deren Abbau zu ββ′-Diaminopyridin und über das αα′-Diaminopyridin |url=https://zenodo.org/record/1814560 |journal=Monatshefte für Chemie |language=de |volume=35 |issue=2 |pages=207–217 |doi=10.1007/BF01518124 |issn=0026-9247|url-access= |url-status= |archive-url= |archive-date= }}{{Cite book |last=Wolffenstein |first=Richard |url=https://www.worldcat.org/oclc/913710178 |title=Die Pflanzenalkaloide |date=1922 |isbn=978-3-642-92449-1 |edition=Dritte, verbesserte und vermehrte Auflage |location=Berlin, Heidelberg |pages=67 |language=de |oclc=913710178}}
The acid is sparingly soluble in water and ether. Its melting point of 323 °C is the highest among pyridinedicarboxylic acids. Upon heating, it decarboxylates and decomposes to nicotinic acid:{{cite journal | journal = Philippine Journal of Science | volume = 109 | issue = 1–2 | pages = 19–21 | date = 1980 | title = Preparation of some nicotinic acid derivatives | author = Alam, Mahbub | author2 = Khan, M. Hafeez }}
References
{{Reflist}}
See also
- Dipicolinic acid, an isomeric dicarboxylic acid