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55940

Sigma-Aldrich

3-Hydroxy-2-naphthoic hydrazide

≥98.0%

Synonym(s):

3-Hydroxy-2-naphthydrazide

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About This Item

Linear Formula:
HOC10H6CONHNH2
CAS Number:
5341-58-2
Molecular Weight:
202.21
Beilstein/REAXYS Number:
395153
EC Number:
226-282-7
MDL number:
MFCD00004097
UNSPSC Code:
12352100
PubChem Substance ID:
57651560
NACRES:
NA.22

Quality Level

100

assay

≥98.0%

mp

205-208 °C (lit.)
205-208 °C

SMILES string

NNC(=O)c1cc2ccccc2cc1O

InChI

1S/C11H10N2O2/c12-13-11(15)9-5-7-3-1-2-4-8(7)6-10(9)14/h1-6,14H,12H2,(H,13,15)

InChI key

FDNAQCWUERCJBK-UHFFFAOYSA-N

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Application

3-Hydroxy-2-naphthoic hydrazide may be used to synthesize the following 2-(alkyl/arylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazoles:
  • 2-ethylamino-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-phenethylamino-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-phenylamino-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(p-bromophenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(p-chlorophenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(p-fluorophenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(m-fluorophenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(p-methoxyphenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(p-methylphenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
  • 2-(m-trifluoromethylphenylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazole
It may also be employed for the synthesis of 3-hydroxy-2-naphthaldehyde.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Histochemical demonstration of protein-bound amino groups.
L P WEISS et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 2(1), 29-49 (1954-01-01)
A Pompella et al.
The American journal of pathology, 142(5), 1353-1357 (1993-05-01)
Confocal laser scanning fluorescence microscopy plus image videoanalysis was used to visualize the tissue areas and the subcellular sites first involved by oxidative stress and lipid peroxidation, in the well-established experimental model of lipid peroxidation induced by haloalkane intoxication in
Molecular structure, vibrational spectroscopic, first-order hyperpolarizability and HOMO, LUMO studies of 3-hydroxy-2-naphthoic acid hydrazide.
Karpagam J, et al.
Journal of Raman Spectroscopy, 41(1), 53-62 (2010)
Hatice N Dogan et al.
Bioorganic & medicinal chemistry, 10(9), 2893-2898 (2002-07-12)
Two new series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized for their possible anticonvulsant, antibacterial and antifungal activities. The degree of protection afforded by these compounds at a dose of 100mg/kg i.p. against pentylenetetrazole-induced convulsions in mice ranged from 0 to 90%. Among
Thangaraj Anand et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 17(4), 414-422 (2018-03-06)
An easy to prepare novel vitamin B6 cofactor derivative 3-hydroxy-N'-((3 hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-2-naphthohydrazide (NPY) was synthesized by a one pot condensation reaction of pyridoxal with 3-hydroxy-2-naphthoic hydrazide and applied for the optical detection of Zn2+ and cysteine in the aqueous DMSO medium.
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