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Dinicotinic acid

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Dinicotinic acid
Names
Preferred IUPAC name Pyridine-3,5-dicarboxylic acid
Other names 3,5-Pyridinedicarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 131640
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.177 Edit this at Wikidata
EC Number
  • 207-893-8
Gmelin Reference 279307
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5NO4/c9-6(10)4-1-5(7(11)12)3-8-2-4/h1-3H,(H,9,10)(H,11,12)Key: MPFLRYZEEAQMLQ-UHFFFAOYSA-N
SMILES
  • C1=C(C=NC=C1C(=O)O)C(=O)O
Properties
Chemical formula C7H5NO4
Molar mass 167.120 g·mol
Structure
Crystal structure monoclinic
Space group P21/c, No. 14
Lattice constant a = 9.702 Å, b = 11.153 Å, c = 6.587 Åα = 90°, β = 107.80°, γ = 90°
Formula units (Z) 4
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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).

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:

Decarboxylation

References

  1. Structure reports for 1973 : organic section. Organic compounds. J. Trotter. Dordrecht: Springer. 1975. p. 174. ISBN 978-94-017-3121-8. OCLC 859588799.{{cite book}}: CS1 maint: others (link)
  2. Meyer, Hans; Tropsch, Hans (1914). "Über Dinicotinsäure und deren Abbau zu ββ′-Diaminopyridin und über das αα′-Diaminopyridin". Monatshefte für Chemie (in German). 35 (2): 207–217. doi:10.1007/BF01518124. ISSN 0026-9247.
  3. Wolffenstein, Richard (1922). Die Pflanzenalkaloide (in German) (Dritte, verbesserte und vermehrte Auflage ed.). Berlin, Heidelberg. p. 67. ISBN 978-3-642-92449-1. OCLC 913710178.{{cite book}}: CS1 maint: location missing publisher (link)
  4. Alam, Mahbub; Khan, M. Hafeez (1980). "Preparation of some nicotinic acid derivatives". Philippine Journal of Science. 109 (1–2): 19–21.

See also

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