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Merck
CN

55940

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:
Molecular Weight:
202.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
226-282-7
Beilstein/REAXYS Number:
395153
MDL number:
Assay:
≥98.0%
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InChI key

FDNAQCWUERCJBK-UHFFFAOYSA-N

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)

SMILES string

NNC(=O)c1cc2ccccc2cc1O

assay

≥98.0%

Quality Level

mp

205-208 °C

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

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Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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)
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)
G Nöhammer
Histochemistry, 90(6), 465-473 (1989-01-01)
Previous methods for the histochemical demonstration of DNA were optimized. p-Toluene sulfonic acid as catalyst for hydrazone formation between the aldehydes generated after Feulgen hydrolysis and 3-hydroxy-2-naphthoic acid hydrazide (NAH) was used instead of acetic acid. Modifications of the conditions
G Nöhammer
Histochemistry, 94(5), 485-488 (1990-01-01)
Fixed cells and tissues pretreated with 4-hydroxynonenal were used as models for the histochemical demonstration of protein bound aldehydic groups. The aldehydes were stained with both a modification of the 2,4-dinitrophenylhydrazine method (2,4-DNPH) and the optimized staining using 3-hydroxy-2-naphthoic acid

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