2-Nitro-1-naphthol Chemical Properties

Melting point:

123-125 °C (lit.)

Boiling point:

324.41°C (rough estimate)

Density 

1.3175 (rough estimate)

refractive index 

1.5400 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

pka

6.13±0.50(Predicted)

InChI

InChI=1S/C10H7NO3/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6,12H

InChIKey

MUCCHGOWMZTLHK-UHFFFAOYSA-N

SMILES

C1(O)=C2C(C=CC=C2)=CC=C1[N+]([O-])=O

CAS DataBase Reference

607-24-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Nitro-1-naphthol(607-24-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29089990

MSDS

• Language:English Provider:2-Nitro-1-naphthol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Nitro-1-naphthol Usage And Synthesis

Description

2-Nitro-1-naphthol is an important organic compound with anti-inflammatory properties used as an analytical method for measuring albumin concentration and as an enzyme-labelled substrate in electrochemical immunoassays. The substance reacts with albumin to form a coloured complex which can be detected spectrophotometrically. It is also used as a model system for the study of inflammatory diseases and inhibits p38 kinase activity. In addition, a derivative of 2-Nitro-1-naphthol (4-nitro-1-naphthol) can be used to prepare chromogenic substrates for neutral or slightly acidic hydrolases.

Chemical Properties

yellow-green to ochre-brown powder and/or chunks

Uses

2-Nitro-1-naphthol was employed as substrate for use in an amperometric 3-electrode system for the determination of alkaline phosphatase, the enzyme label most commonly used in electrochemical immunoassays. It was also used in the preparation of:

• di-(2-nitro-1-naphthyl) hydrogen phosphate
• 1-(2′-methyl-3′-indenyl)-2-naphthylamine and -2-naphthol (axially chiral ligands)

Application

2-Nitro-1-naphthol is commonly used as an intermediate in organic synthesis. It is a derivative of 1-nitro-2-naphthol and 4-nitro-1-naphthol. 1-Nitro-2-naphthol has been found to be a potent inhibitor of enzyme-dependent activation of acetyl-CoA, while 4-nitro-1-naphthol facilitates the preparation of chromogenic substrates for neutral or slightly acidic hydrolases^[1-2].

Purification Methods

Crystallise the naphthol (repeatedly) from EtOH. [Beilstein 6 H 615, 6 III 2938, 6 IV 4236.]

References

[1] JIZHENG DANG . Chromogenic substrate from 4-nitro-1-naphthol for hydrolytic enzyme of neutral or slightly acidic optimum pH: 4-Nitro-1-naphthyl-β-d-galactopyranoside as an example[J]. Bioorganic & Medicinal Chemistry Letters, 2013. DOI:10.1016/j.bmcl.2012.11.120.
[2] ATSUKO SHINOHARA. Inhibition of acetyl-coenzyme A dependent activation of N-hydroxyarylamines by phenolic compounds, pentachlorophenol and 1-nitro-2-naphthol[J]. Chemico-Biological Interactions, 1986. DOI:10.1016/0009-2797(86)90058-X.

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