| Identification | More | [Name]
2-Nitro-1-naphthol | [CAS]
607-24-9 | [Synonyms]
2-NITRO-1-NAPHTHOL
2-Nitro-1-Napthol
2-Nitronaphth-1-ol
2-Nitro-2-naphthol
1-Naphthalenol, 2-nitro-
2-Nitronaphthalen-1-ol | [EINECS(EC#)]
210-131-7 | [Molecular Formula]
C10H7NO3 | [MDL Number]
MFCD00003956 | [Molecular Weight]
189.17 | [MOL File]
607-24-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow-green to ochre-brown powder and/or chunks | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29089990 |
| Hazard Information | Back Directory | [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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