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1-(2-Pyridylazo)-2-naphthol

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1-(2-Pyridylazo)-2-naphthol Basic information

Product Name:
1-(2-Pyridylazo)-2-naphthol
Synonyms:
  • 1-(2-pyridinylazo)-2-naphthaleno
  • 1-(2-Pyridylazo)-2-Hydroxynaphthalene
  • O-PAN
  • 1-(2-Pyridylazo)-2-n
  • 1-(2-Pyridylazo)-2-naphthol 99%
  • 1-[(E)-2-Pyridinyldiazenyl]-2-naphthol
  • 2-Hydroxy-1-(2-pyridylazo)naphthalene
  • 2-Naphthol, 1-(2-pyridylazo)-
CAS:
85-85-8
MF:
C15H11N3O
MW:
249.27
EINECS:
201-637-9
Product Categories:
  • Pyridylazo Compounds
  • Analytical Chemistry
  • Azo Compounds
  • Chelating Reagents
  • Naphthylazo Compounds
  • Intermediates
Mol File:
85-85-8.mol
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1-(2-Pyridylazo)-2-naphthol Chemical Properties

Melting point:
138-141 °C (lit.)
Boiling point:
392.37°C (rough estimate)
Density 
1.1469 (rough estimate)
bulk density
190kg/m3
refractive index 
1.5700 (estimate)
storage temp. 
Store at +5°C to +30°C.
pka
8.86±0.50(Predicted)
form 
Powder/Solid
color 
green to red, upon chelation with metal
Water Solubility 
Insoluble
λmax
461-465 nm in ethanol
ε(extinction coefficient)
≥15000 at 462-468nm in methanol at 0.01g/L
>35,000 at 222-228nm in methanol at 0.01g/L
>9,000 at 300-306nm in methanol at 0.01g/L
BRN 
206390
Stability:
Stable. Incompatible with strong oxidizing agents, strong bases.
CAS DataBase Reference
85-85-8(CAS DataBase Reference)
NIST Chemistry Reference
2-Naphthalenol, 1-(2-pyridinylazo)-(85-85-8)
EPA Substance Registry System
2-Naphthalenol, 1-(2-pyridinylazo)- (85-85-8)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
TSCA 
Yes
HS Code 
29333999

MSDS

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1-(2-Pyridylazo)-2-naphthol Usage And Synthesis

Uses

1-(2-Pyridylazo)-2-naphthol is an indicator of transition metals. 1-(2-Pyridylazo)-2-naphthol is an indicator in complexometry and a reagent for the extraction and spectrophotometric determination of many transition metals. Dyes and metabolites.

Chemical Properties

orange crystals

Uses

1-(2-Pyridylazo)-2-naphthol is an indicator of transition metals. 1-(2-Pyridylazo)-2-naphthol is an indicator in complexometry and a reagent for the extraction and spectrophotometric determination of many transition metals. Dyes and metabolites.

Definition

ChEBI: 1-(2-pyridin-2-yldiazenyl)-2-naphthol is a member of naphthols.

General Description

1-(2-Pyridylazo)-2-naphthol (PAN), an orange colored dye, is commonly used as an acid-base indicator. It can form chelates with metal ions, which makes it a valuable indicator in complexometric titrations. PAN is also a spectrophotometric reagent, which can extract metal chelates into an organic solvent.

Agricultural Uses

1-(2-Pyridylazo)-2-naphthol is a hard stratum of strongly compacted soil caused by continual plowing to the same depth of hardened soil which has high clay content. The precipitated iron and silicates cement the soil particles and form pans. 1-(2-Pyridylazo)-2-naphthol often impede drainage and root growth. It can be broken up using a subsoiler .

Purification Methods

Purify PAN by repeated crystallisation from EtOH or MeOH. It can also be purified by sublimation under vacuum. Purity can be checked by TLC using a mixed solvent (pet ether/Et2O/EtOH; 10:10:1) on a silica gel plate. It has pK1 1.9 and pK2 12.2 in 20% aqueous ethoxyethanol. It chelates with copper [Pease & Williams Anal Chem 31 1046 1959]. [Beilstein 22 I 694, 22 III/IV 7073, 22/4 V 618.]

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