1-Nitroso-2-naphthol is an organic compound with the formula C10H6(NO)OH. It is one of several possible nitrosonaphthols, and the most studied for applications as an indicator and a dye.[2]
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3D model (JSmol)
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| ECHA InfoCard | 100.004.586 |
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CompTox Dashboard (EPA)
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| Properties | |
| C10H7NO2 | |
| Molar mass | 173.171 g·mol−1 |
| Appearance | Yellowish-brown |
| Melting point | 109.5 °C (229.1 °F; 382.6 K) |
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| GHS labelling:[1] | |
 
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| H302, H315, H319, H335, H400 | |
| P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions edit
1-Nitroso-2-naphthol can be prepared by treatment of 2-naphthol with nitrous acid:[3]
- C10H7OH + HNO2 → C10H6(NO)OH + H2O
Its conjugate base forms deeply colored complexes with iron(II) and cobalt(II), complexes [M(C10H6(NO)O)3]2-.[4] The deep colors of these complexes results from the delocalized bonding within each five-membered chelate ring. These species can be classified as nitroso complexes.
See also edit
- Naphthol Green B, the iron complex of a sulfonated derivative of 1-nitroso-2-naphthol
References edit
- ^ "1-Nitroso-2-naphthol". pubchem.ncbi.nlm.nih.gov.
- ^ Gledhill, Martha; Van Den Berg, Constant M.G. (1994). "Determination of complexation of iron(III) with natural organic complexing ligands in seawater using cathodic stripping voltammetry". Marine Chemistry. 47 (1): 41–54. Bibcode:1994MarCh..47...41G. doi:10.1016/0304-4203(94)90012-4.
- ^ Marvel, C. S.; Porter, P. K. (1922). "Nitroso-β-Naphthol". Organic Syntheses. 2: 61. doi:10.15227/orgsyn.002.0061.
- ^ Wang, Xiao; Zhang, Tianyong; Li, Bin; Yang, Qiusheng; Jiang, Shuang (2014). "Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H2O2". Applied Organometallic Chemistry. 28 (9): 666–672. doi:10.1002/aoc.3178.