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5-Aminonicotinic acid

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CAS:24242-19-1
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5-Aminonicotinic acid Basic information
Product Name:5-Aminonicotinic acid
Synonyms:3-PYRIDINECARBOXYLIC ACID, 5-AMINO-;5-AMINO-3-PYRIDINECARBOXYLIC ACID;5-AMINOPYRIDINE-3-CARBOXYLIC ACID;5-AMINONICOTINIC ACID;AKOS BBS-00001362;5-AMINOSONICOTINICACID;5-AMINOISOPHTHALICACID;IFLAB-BB F1926-0005
CAS:24242-19-1
MF:C6H6N2O2
MW:138.12
EINECS:625-282-8
Product Categories:Carboxylic Acids;AMINOACID;Amines;blocks;Carboxes;Pyridines;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;pharmacetical;Carboxylic Acids
Mol File:24242-19-1.mol
5-Aminonicotinic acid Structure
5-Aminonicotinic acid Chemical Properties
Melting point 293 °C
Boiling point 253.51°C (rough estimate)
density 1.3471 (rough estimate)
refractive index 1.5100 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka2.36±0.10(Predicted)
form Crystalline Powder
color Golden-brown
BRN 115848
InChIInChI=1S/C6H6N2O2/c7-5-1-4(6(9)10)2-8-3-5/h1-3H,7H2,(H,9,10)
InChIKeyBYIORJAACCWFPU-UHFFFAOYSA-N
SMILESC1=NC=C(N)C=C1C(O)=O
CAS DataBase Reference24242-19-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/37/38-20/21/22-22
Safety Statements 36/37/39-26-36
WGK Germany 3
HazardClass IRRITANT
HS Code 29333990
MSDS Information
ProviderLanguage
ACROS English
5-Aminonicotinic acid Usage And Synthesis
Chemical PropertiesOff-white Cryst
Uses5-Aminonicotinic acid is used in the synthesis of coordination polymers, bioluminescent reagents and biological active agents.
DefinitionChEBI: 5-aminonicotinic acid is an aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring. It has a role as a metabolite. It is an aromatic amine, an aminopyridine and an aminonicotinic acid. It is functionally related to a nicotinic acid.
Synthesis
5-Bromonicotinic acid

20826-04-4

5-Aminonicotinic acid

24242-19-1

The general procedure for the synthesis of 5-aminonicotinic acid from 5-bromonicotinic acid was as follows: 5-bromo-3-pyridinecarboxylic acid (25 g, 0.124 mol) was mixed with ammonia (67.32 mL) and copper sulfate pentahydrate (8.41 g) was added. The reaction mixture was transferred to an autoclave, heated to 120 °C and kept for 16 hours. The reaction process was monitored by thin layer chromatography (TLC) using ninhydrin as a color developer. Upon completion of the reaction, the reaction mixture was washed with saturated sodium sulfide solution to remove copper ions, followed by adjusting the pH to 4-5 with concentrated hydrochloric acid.The acidified mixture was cooled to precipitate solids. The solid product was collected by filtration and dried to give 5-aminonicotinic acid (12.9 g, 74% yield).

References[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[2] Patent: WO2004/35545, 2004, A2. Location in patent: Page 46
[3] Patent: WO2003/101959, 2003, A1. Location in patent: Page 50-51
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1981, vol. 35, # 4, p. 289 - 294
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 2381,2383
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