1-Nitroso-2-naphthol

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1-Nitroso-2-naphthol
1-nitroso-2-naphthol.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.586 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-043-0
PubChem CID
UNII
  • InChI=1S/C10H7NO2/c12-9-6-5-7-3-1-2-4-8(7)10(9)11-13/h1-6,12H
    Key: YXAOOTNFFAQIPZ-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC(=C2N=O)O
Properties
C10H7NO2
Molar mass 173.171 g·mol−1
AppearanceYellowish-brown
Melting point 109.5 °C (229.1 °F; 382.6 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
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).

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]

Contents

Synthesis and reactions

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

Related Research Articles

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<span class="mw-page-title-main">2-Aminophenol</span> Chemical compound

2-Aminophenol is an organic compound with the formula C6H7NO. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallized from hot water.

<span class="mw-page-title-main">Martius yellow</span> Chemical compound

Martius yellow is an organic compound that once was used to protect wool from moths. It is prepared by nitration of naphthol.

<span class="mw-page-title-main">Naphthol Green B</span> Chemical compound

Naphthol Green B is a coordination complex of iron that is used as a dye. The ligand is a sulfonated derivative of 1-nitroso-2-naphthol.

A hydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

<span class="mw-page-title-main">Naphthionic acid</span> Chemical compound

Naphthionic acid is an organic compound with the formula C10H6(SO3H)(NH2). It is one of several aminonaphthalenesulfonic acids, derivatives of naphthalene containing both amine and sulfonic acid functional groups. It is a white solid, although commercial samples can appear gray. It is used in the synthesis of azo dyes such as Rocceline (a. k. a. Solid Red A), during which the amino group of the acid (in the form of a salt) is diazotated and then coupled with, in the case mentioned, β-naphthol. It is prepared by treating 1-aminonaphthalene with sulfuric acid.

<span class="mw-page-title-main">Naphthol AS</span> Chemical compound

Naphthol AS is an organic compound with the formula C10H6(OH)C(O)NHC6H5. It is the anilide of 3-hydroxy-2-carboxynaphthalene. Many analogous compounds are known, designated with a differing suffix. For example, in Naphthol AS-OL, the aryl substituent on nitrogen is C6H4-2-OCH3. These compounds are used as coupling partners in the preparation of some azo dyes.

<span class="mw-page-title-main">3-Hydroxy-2-naphthoic acid</span> Chemical compound

3-Hydroxy-2-naphthoic acid is an organic compound with the formula C10H6(OH)(CO2H). It is one of the several hydroxynaphthoic acids. It is a precursor to some azo dyes and pigments. It is prepared by carboxylation of 2-naphthol by the Kolbe–Schmitt reaction.

<span class="mw-page-title-main">2-Hydroxy-1-naphthoic acid</span> Chemical compound

2-Hydroxy-1-naphthoic acid is an organic compound with the formula C10H6(OH)(CO2H). It is prepared by carboxylation of 2-naphthol by the Kolbe–Schmitt reaction. It is one of several hydroxynaphthoic acids.

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.