ChemicalBook--->CAS DataBase List--->24242-19-1

24242-19-1

24242-19-1 Structure

24242-19-1 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
[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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Thionyl chloride-->Nitric acid-->Bromine-->Ammonium hydroxide-->Sodium sulfide-->Nicotinic acid-->Copper(II) sulfate pentahydrate-->Sodium sulfide nonahydrate-->Ninhydrin hydrate-->3-Bromoquinoline-->5-Bromonicotinic acid
[Preparation Products]

5-Amino-3-pyridinemethanamine-->5-Amino-3-pyridinecarbonitrile-->5-Hydroxynicotinic acid-->(5-Fluoropyridin-3-yl)methanol ,97%-->5-Amino-3-pyridinecarboxamide-->3-Amino-5-hydroxymethylpyridine-->Methyl 5-fluoropyridine-3-carboxylate-->Ethyl 5-fluoronicotinate-->Methyl 5-hydroxynicotinate-->5-Hydroxy-nicotinic acid ethyl ester-->5-Acetamidonicotinic acid-->Methyl 5-aminopyridine-3-carboxylate-->Ethyl 5-aminopyridine-3-carboxylate ,97%-->Ethyl 5-(2-phenyleth-1-ynyl)nicotinate
Hazard InformationBack 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]

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
Spectrum DetailBack Directory
[Spectrum Detail]

5-Aminonicotinic acid(24242-19-1)MS
5-Aminonicotinic acid(24242-19-1)1HNMR
5-Aminonicotinic acid(24242-19-1)IR1
5-Aminonicotinic acid(24242-19-1)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

5-Aminonicotinic acid, 95%(24242-19-1)
[TCI AMERICA]

5-Aminonicotinic Acid,>98.0%(LC)(T)(24242-19-1)
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