2-Nitro-1-naphthol
- CAS NO.:607-24-9
- Empirical Formula: C10H7NO3
- Molecular Weight: 189.17
- MDL number: MFCD00003956
- EINECS: 210-131-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-02-07 14:56:38
What is 2-Nitro-1-naphthol?
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
The Uses of 2-Nitro-1-naphthol
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)
What are the applications of 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.
Properties of 2-Nitro-1-naphthol
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 |
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 |
CAS DataBase Reference | 607-24-9(CAS DataBase Reference) |
NIST Chemistry Reference | 2-Nitro-1-naphthol(607-24-9) |
Safety information for 2-Nitro-1-naphthol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Nitro-1-naphthol
InChIKey | MUCCHGOWMZTLHK-UHFFFAOYSA-N |
SMILES | C1(O)=C2C(C=CC=C2)=CC=C1[N+]([O-])=O |
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