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55940

Sigma-Aldrich

3-Hydroxy-2-naphthoic hydrazide

≥98.0%

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Synonym(s):
3-Hydroxy-2-naphthydrazide
Linear Formula:
HOC10H6CONHNH2
CAS Number:
Molecular Weight:
202.21
Beilstein:
395153
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
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)
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
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.
M Thomas et al.
The Histochemical journal, 26(3), 189-196 (1994-03-01)
Factors which influence the iron-stimulated lipid peroxidation in rat liver have been studied by incubating unfixed cryostat sections with a pro-oxidant system and using an optimized histochemical detection method for lipid peroxidation products with 3-hydroxy-2-naphthoic acid hydrazide and Fast Blue

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