Dinicotinic acid

Dinicotinic acid
Names
Preferred IUPAC name
Pyridine-3,5-dicarboxylic acid
Other names
3,5-Pyridinedicarboxylic acid
Identifiers
CAS Number
  • 499-81-0
3D model (JSmol)
  • Interactive image
Beilstein Reference
 131640
ChEBI
  • CHEBI:46875
ChEMBL
  • ChEMBL446761
ChemSpider
  • 9939
ECHA InfoCard 100.007.177 Edit this at Wikidata
EC Number
  • 207-893-8
Gmelin Reference
 279307
PubChem CID
  • 10366
UNII
  • N5NMH4PZ3D checkY
CompTox Dashboard (EPA)
  • DTXSID10198149 Edit this at Wikidata
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
  • C1=C(C=NC=C1C(=O)O)C(=O)O
Properties
Chemical formula
 C7H5NO4
Molar mass 167.120 g·mol−1
Structure[1]
Crystal structure
 monoclinic
Space group
 P21/c, No. 14
Lattice constant
a = 9.702 Å, b = 11.153 Å, c = 6.587 Å
α = 90°, β = 107.80°, γ = 90°
Formula units (Z)
 4
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
H315, H319, H335
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 [77 °F], 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).[2][3]

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:[4]

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