1-Nitroso-2-naphthol
{{Chembox
| ImageFile = 1-nitroso-2-naphthol.svg
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|Section1={{Chembox Identifiers
| CASNo = 131-91-9
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 8262
| EC_number = 205-043-0
| UNII = 757I55U2QX
| PubChem = 8580
| StdInChI=1S/C10H7NO2/c12-9-6-5-7-3-1-2-4-8(7)10(9)11-13/h1-6,12H
| StdInChIKey = YXAOOTNFFAQIPZ-UHFFFAOYSA-N
| SMILES = C1=CC=C2C(=C1)C=CC(=C2N=O)O
}}
|Section2={{Chembox Properties
| C = 10|N=1|O=2|H=7
| Appearance = Yellowish-brown
| Density =
| MeltingPtC = 109.5
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|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|319|335|400}}
| PPhrases = {{P-phrases|261|264|264+265|270|271|273|280|301+317|302+352|304+340|305+351+338|319|321|330|332+317|337+317|362+364|391|403+233|405|501}}
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1-Nitroso-2-naphthol is an organic compound with the formula {{chem2|C10H6(NO)OH}}. It is one of several possible nitrosonaphthols, and the most studied for applications as an indicator and a dye.{{cite journal |doi=10.1016/0304-4203(94)90012-4 |title=Determination of complexation of iron(III) with natural organic complexing ligands in seawater using cathodic stripping voltammetry |date=1994 |last1=Gledhill |first1=Martha |last2=Van Den Berg |first2=Constant M.G. |journal=Marine Chemistry |volume=47 |issue=1 |pages=41–54 |bibcode=1994MarCh..47...41G }}
Synthesis and reactions
1-Nitroso-2-naphthol can be prepared by treatment of 2-naphthol with nitrous acid:{{cite journal |doi=10.15227/orgsyn.002.0061|journal=Organic Syntheses |year=1922 |volume=2 |page=61 |title=Nitroso-β-Naphthol |first1=C. S.|last1=Marvel|first2=P. K.| last2=Porter}}
:{{chem2|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-.{{cite journal |doi=10.1002/aoc.3178 |title=Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H2O2 |date=2014 |last1=Wang |first1=Xiao |last2=Zhang |first2=Tianyong |last3=Li |first3=Bin |last4=Yang |first4=Qiusheng |last5=Jiang |first5=Shuang |journal=Applied Organometallic Chemistry |volume=28 |issue=9 |pages=666–672 }} 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
- Naphthol Green B, the iron complex of a sulfonated derivative of 1-nitroso-2-naphthol