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Pyridine-2-carboxylic acid hydrazide

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Pyridine-2-carboxylic acid hydrazide manufacturers

Pyridine-2-carboxylic acid hydrazide Basic information
Product Name:Pyridine-2-carboxylic acid hydrazide
Synonyms:AKOS B014996;AKOS BBS-00004147;2-PICOLINYL HYDRAZIDE;ART-CHEM-BB B014996;PYRIDINE-2-CARBOHYDRAZIDE;2-pyridinecarboxylic acid hydrazide;2-PICOLINYL HYDRAZIDE 98+%;NSC-81875
CAS:1452-63-7
MF:C6H7N3O
MW:137.14
EINECS:
Product Categories:Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Amines;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;AMIDE
Mol File:1452-63-7.mol
Pyridine-2-carboxylic acid hydrazide Structure
Pyridine-2-carboxylic acid hydrazide Chemical Properties
Melting point 100°C
Boiling point 100-102 °C
density 1.244
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka11.29±0.10(Predicted)
color White to Off-White
InChI1S/C6H7N3O/c7-9-6(10)5-3-1-2-4-8-5/h1-4H,7H2,(H,9,10)
InChIKeyBAQLNPIEFOYKNB-UHFFFAOYSA-N
SMILESNNC(=O)c1ccccn1
CAS DataBase Reference1452-63-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-36/37/39-24/25
WGK Germany WGK 3
HazardClass IRRITANT
HS Code 29333990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
MSDS Information
Pyridine-2-carboxylic acid hydrazide Usage And Synthesis
Chemical PropertiesWhite to off-white solid
UsesPyridine-2-carboxylic acid hydrazide is an impurity of Isoniazid (I821450), which is an antibiotic for treatment of Mycobacterium tuberculosis and inhibits mycolic acid biosynthesis. Intermediate used for the synthesis of analogs of antitumor agent 1-acetyl-2-picolinoylhydrazine.
Synthesis
Ethyl picolinate

2524-52-9

PYRIDINE-2-CARBOXYLIC ACID HYDRAZIDE

1452-63-7

General procedure for the synthesis of 2-pyridinecarbohydrazide from ethyl 2-pyridinecarboxylate: a mixed solution of ethyl pyridine-2-carboxylate (90 g) and hydrazine hydrate (60 g) in ethanol (400 ml) was reacted with stirring at 80°C for 4 hours. After completion of the reaction, the solvent was removed by evaporation to give the crude product. The crude product was co-stirred with ether and the resulting suspension was filtered and the wet filter cake was washed with a small amount of ethanol (50 mL) to give 76 g (93% yield) of 2-pyridinecarbohydrazide as a white solid. Mass spectral data: m/z 138.0 (M+H).

References[1] Patent: WO2010/136971, 2010, A1. Location in patent: Page/Page column 12
[2] Patent: US2012/142710, 2012, A1. Location in patent: Page/Page column 6
[3] Patent: WO2012/76989, 2012, A1. Location in patent: Page/Page column 55; 64
[4] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5535 - 5542
[5] Patent: WO2017/106427, 2017, A1. Location in patent: Page/Page column 37-38
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