2-Nitro-1-naphthol Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Nitro-1-naphthol Chemical Properties,Usage,Production

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.