| Identification | More | [Name]
5-Aminonicotinic acid | [CAS]
24242-19-1 | [Synonyms]
3-PYRIDINECARBOXYLIC ACID, 5-AMINO-
5-AMINO-3-PYRIDINECARBOXYLIC ACID
5-AMINONICOTINIC ACID
5-AMINOPYRIDINE-3-CARBOXYLIC ACID
AKOS BBS-00001362
AURORA KA-3032
IFLAB-BB F1926-0005
OTAVA-BB BB7017520056
3-Amino-5-pyridinecarboxylic acid
3-Pyridinecarboxylicacid,5-amino-(9CI)
5-AMINOSONICOTINICACID
5-AMINOISOPHTHALICACID
5-Aminonicotinic acid ,98% | [EINECS(EC#)]
625-282-8 | [Molecular Formula]
C6H6N2O2 | [MDL Number]
MFCD00129116 | [Molecular Weight]
138.12 | [MOL File]
24242-19-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [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 | [form ]
Crystalline Powder | [pka]
2.36±0.10(Predicted) | [color ]
Golden-brown | [Detection Methods]
HPLC,NMR | [BRN ]
115848 | [InChI]
InChI=1S/C6H6N2O2/c7-5-1-4(6(9)10)2-8-3-5/h1-3H,7H2,(H,9,10) | [InChIKey]
BYIORJAACCWFPU-UHFFFAOYSA-N | [SMILES]
C1=NC=C(N)C=C1C(O)=O | [CAS DataBase Reference]
24242-19-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
5-Aminonicotinic acid is used in the synthesis of coordination polymers, bioluminescent reagents and biological active agents. | [Definition]
ChEBI: 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]
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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