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

|Structure_ref={{Cite book |url=https://books.google.com/books?id=3H7vCAAAQBAJ&pg=PA174 |title=Structure reports for 1973 : organic section. Organic compounds |date=1975 |publisher=Springer |others=J. Trotter |isbn=978-94-017-3121-8 |location=Dordrecht |pages=174 |oclc=859588799}}

|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 }}

: File:Dinicotinic Acid–– Nicotinic Acid V1.svg

References

{{Reflist}}

See also