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1-Nitroso-2-naphthol

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1-Nitroso-2-naphthol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.586 Edit this at Wikidata
EC Number
  • 205-043-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H7NO2/c12-9-6-5-7-3-1-2-4-8(7)10(9)11-13/h1-6,12HKey: YXAOOTNFFAQIPZ-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C=CC(=C2N=O)O
Properties
Chemical formula C10H7NO2
Molar mass 173.171 g·mol
Appearance Yellowish-brown
Melting point 109.5 °C (229.1 °F; 382.6 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H315, H319, H335, H400
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

Synthesis and reactions

1-Nitroso-2-naphthol can be prepared by treatment of 2-naphthol with nitrous acid:

C10H7OH + HNO2 → C10H6(NO)OH + H2O

Its conjugate base forms deeply colored complexes with iron(II) and cobalt(II), complexes . 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

References

  1. "1-Nitroso-2-naphthol". pubchem.ncbi.nlm.nih.gov.
  2. 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.
  3. Marvel, C. S.; Porter, P. K. (1922). "Nitroso-β-Naphthol". Organic Syntheses. 2: 61. doi:10.15227/orgsyn.002.0061.
  4. 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.
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