132-53-6

Basic information

• Product Name: 2-Nitroso-1-naphthol
• Synonyms: 2-nitroso-1-Naphthalenol;2-nitroso-1-naphtho;2-Nitrosonaphthol;beta-Nitrosonaphthol;C.I. 76610;ci76610;2-NITROSO-1-NAPHTHOL;1,2-NAPHTHOQUINONE 2-OXIME
• CAS NO: 132-53-6
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.17
• EINECS: 205-064-5
• Product Categories: Intermediates of Dyes and Pigments;Piperazine derivates;Nitroso Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 132-53-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 150-155 °C (dec.)(lit.)
• Boiling Point: 303.81°C (rough estimate)
• Flash Point: 170.1 °C
• Appearance: purple-yellow solid.
• Density: 1.2427 (rough estimate)
• Vapor Pressure: 1.31E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• PKA: 7.47±0.10(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 1867919
• CAS DataBase Reference: 2-Nitroso-1-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitroso-1-naphthol(132-53-6)
• EPA Substance Registry System: 2-Nitroso-1-naphthol(132-53-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: QL4550000
• F: 8
• Hazardous Substances Data: 132-53-6(Hazardous Substances Data)

Usage

Description

2-Nitroso-1-naphthol is a chemical compound characterized by its yellow-greenish to yellow-brownish powder form. It is primarily recognized for its role as a selective complexing agent in the extraction of cobalt ions and is also utilized in the separation and preconcentration of various metal ions through solid phase extraction techniques.

Uses

Used in Chemical Analysis:
2-Nitroso-1-naphthol is used as a selective complexing agent for the extraction of cobalt ions. Its application in this field is crucial for accurate and efficient analysis of cobalt ion concentrations in various samples.
Used in Metal Ion Separation and Preconcentration:
In the field of metal ion separation and preconcentration, 2-Nitroso-1-naphthol is employed as a complexing agent to facilitate the separation and concentration of Th(IV), Ti(IV), Fe(III), Pb(II), and Cr(III) ions. This application is vital for enhancing the efficiency of metal ion analysis and detection in various industries, including environmental monitoring, mining, and metallurgy.
Used in Environmental Monitoring:
2-Nitroso-1-naphthol plays a significant role in environmental monitoring as it aids in the detection and analysis of metal ion contaminants. Its use in this industry helps to ensure the safety and quality of environmental samples, contributing to the protection of ecosystems and human health.
Used in Mining and Metallurgy:
In the mining and metallurgy industries, 2-Nitroso-1-naphthol is utilized for the separation and preconcentration of valuable metal ions. Its application in these industries aids in the efficient extraction and processing of metals, ultimately contributing to the overall productivity and profitability of mining and metallurgical operations.

Safety Profile

Moderately toxic by ingestion. Many nitroso compounds are carcinogens. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NOx. See also NITROSO COMPOUNDS.

Purification Methods

Purify the naphthol by recrystallisation from pet ether (b 60-80o) or by dissolving it in hot EtOH, followed by successive addition of small volumes of water (m 158o dec). It also crystallises from *C6H6 or H2O. Crystallisation from *C6H6/pet ether gives m (106-109 o, also 109.5o). It has max at 274.5 and 382nm (CHCl3). It complexes with metals. [Beilstein 7 H 712, 7 I 385, 7 II 647, 7 III 3688, 7 IV 2419.]

InChI:InChI=1/C10H7NO2/c12-10-8-4-2-1-3-7(8)5-6-9(10)11-13/h1-6,12H/p-1

Synthetic route

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6) + 4-nitroso-1-naphthol (605-60-7)

Conditions	Yield
With 1-butyl-3-methylimidazolium nitrite; boric acid for 0.0416667h; Microwave irradiation; Neat (no solvent); regioselective reaction;	A 72% B n/a

1-hydroxy-2-naphthoic acid (86-48-6) → 2-Nitroso-1-naphthol (132-53-6)

Conditions	Yield
With sulfuric acid; sodium hydroxide; sodium nitrite In water for 5h;	70%
With sodium hydroxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sodium nitrite anschl. Ansaeuern mit verd. Schwefelsaeure;

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6) + 1,4-naphthoquinone 1-oxime (4965-30-4)

Conditions	Yield
With sodium nitrite In water; propionic acid at -5℃;	A 63% B 22%
With i-AmNO2; potassium carbonate In N,N-dimethyl-formamide Ambient temperature;	A 26% B 59%

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6) + 4-nitroso-2-naphthol

Conditions	Yield
With hydrogenchloride In water at 0 - 5℃; for 0.916667h;	A 56% B 35%

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6) + 4-nitroso-1-naphthol (605-60-7) + 2-nitro-1-naphthol (607-24-9)

Conditions	Yield
With acetic acid; sodium nitrite In ethanol for 0.0833333h; Nitrosation; nitration;	A 17% B 42% C 8%

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6)

Conditions	Yield
With zinc(II) chloride; sodium nitrite In ethanol for 3h; Nitrosation; Heating;	36%
With zinc(II) chloride; sodium nitrite
With potassium hydroxide; potassium nitrite; water anschliessend Hinzugeben von konz. Schwefelsaeure;
With sodium nitrite Reaktion ueber mehrere Stufen;
With acetic acid; sodium hydroxide; sodium nitrite In water for 1h;

α-naphthol (90-15-3) + Cyclopropylamine (765-30-0) → 2-Nitroso-1-naphthol (132-53-6) + 4-nitroso-1-naphthol (605-60-7) + 4-(cyclopropylazo)-1-naphthol + 2-(cyclopropylazo)-1-naphthol

Conditions	Yield
With isopentyl nitrite In chloroform at 5℃; for 16h; Further byproducts given;	A 3% B 7% C 30% D n/a

α-naphthol (90-15-3) → 2-Nitroso-1-naphthol (132-53-6) + [1,4]naphthoquinone monooxime (4965-30-4)

Conditions	Yield
With potassium nitrite; sulfuric acid
With nitrosylsulfuric acid

2-nitronaphthalene (581-89-5) → 2-Nitroso-1-naphthol (132-53-6)

Conditions	Yield
With potassium carbonate at 55℃;

1,2-naphthoquinone (524-42-5) → 2-Nitroso-1-naphthol (132-53-6)

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

naphthalen-2-ylamine (91-59-8) → 2-Nitroso-1-naphthol (132-53-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / Behandeln der Loesung mit NaNO2 und Wasser bei 0grad, anschliessend mit Kupferoxydul 2: methanolic potash / 55 °C View Scheme

sodium hexanitrocobaltate(III) + 2-Nitroso-1-naphthol (132-53-6) → {Co(β.α-C10H6NO2)3}

Conditions	Yield
In methanol; water a soln. of ligand in MeOH was added to a soln. of salt in water, the mixt. was stirred for 2 h; ppt. was filtered off; elem.anal.;	98%

cobalt(II) chloride hexahydrate + 2-Nitroso-1-naphthol (132-53-6) → {Co(β.α-C10H6NO2)3}

Conditions	Yield
In methanol under N2, a soln. of salt was added to a soln. of ligand (1:3.5 molar ratio) and the mixt. was stirred for 3 h; ppt. was filtered off, washed with MeOH and dried at 100°C, chromd; elem.anal.;	97%
In methanol under N2, a soln. of salt was added to a soln. of ligand (1:5 molar ratio) and the mixt. was stirred for 3 h; ppt. was filtered off, washed with MeOH and dried at 100°C, chromd; elem.anal.;	97%
In methanol in air, a soln. of salt was added to a soln. of ligand (1:3.5 molar ratio) and the mixt. was stirred for 3 h; ppt. was filtered off, washed with MeOH and dried at 100°C, chromd; elem.anal.;	95%
In methanol in air, a soln. of salt was added to a soln. of ligand (1:3.0 molar ratio) and the mixt. was stirred for 3 h; ppt. was filtered off, washed with MeOH and dried at 100°C, chromd; elem.anal.;	83%
In methanol under N2, a soln. of salt was added to a soln. of ligand (1:2.5 molar ratio) and the mixt. was stirred for 3 h; ppt. was filtered off, washed with MeOH and dried at 100°C, chromd; elem.anal.;	69%

2-Nitroso-1-naphthol (132-53-6) → 2-nitro-1-naphthol (607-24-9)

Conditions	Yield
With nitrogen(II) oxide In benzene at 20℃; for 2h;	96%
With dihydrogen peroxide; nitric acid In acetic acid

sodium hexanitrocobaltate(III) + 2-Nitroso-1-naphthol (132-53-6) → sodium dinitrobis(1,2-naphthoquinone-1-oximato)cobaltate(III)

Conditions	Yield
With NaNO2 In methanol; water a soln. of ligand in MeOH was added to a stirred soln. of salt and NaNO2 in water, mixt. was stirred for 2 h; mixt. was dried and then extd. with acetone, solvent was removed;elem.anal.;	95%

copper(ll) sulfate pentahydrate + 2-Nitroso-1-naphthol (132-53-6) → bis(2-nitroso-1-naphtholato)copper(II) monohydrate

Conditions	Yield
With acetic acid In water for 16h;	90%

2-Nitroso-1-naphthol (132-53-6) + 2-methylnaphtho<2,3-d>thiazole-4,9-dione 3-methiodides → 2-{[(E)-1-Hydroxy-naphthalen-2-ylimino]-methyl}-3-methyl-4,9-dioxo-4,9-dihydro-naphtho[2,3-d]thiazol-3-ium; iodide

Conditions	Yield
With piperidine In ethanol for 8h; Heating;	88%

nickel(II) chloride hexahydrate + 2-Nitroso-1-naphthol (132-53-6) → bis(1-naphthoquinone-2-oximato)nickel(II)

Conditions	Yield
With NH3 In ethanol; water dropwise addn. of 20 % stoich. excess of ligand (in EtOH/H2O=1:1) to NiCl2 and concd. NH3 (in H2O); filtration (after 48 h), washing (H2O, EtOH), extn. (MeOH), drying of residue (20°C, 0.1 Torr); elem. anal.;	86%

2-Nitroso-1-naphthol (132-53-6) + 3,9-dimethyl-5,11-dioxo-1,7-diphenyl-2,8-diethyl-5,11-dihydrobenzo[2,3-b;2',3'-b']bis(pyrazolo[4,5-b]-1,4-oxazinium iodide) → C40H33N7O5(2+)*2I(1-)

Conditions	Yield
With piperidine In ethanol for 7h; Reflux;	85%

2-Nitroso-1-naphthol (132-53-6) + N,N'-(1,4-phenylene)bis(2-cyano-3-(dimethylamino)acrylamide) → N,N'-(1,4-phenylene)bis(2-oxo-2,5-dihydronaphtho[1,2-b][1,4]oxazepine-3-carboxamide)

Conditions	Yield
With acetic acid; zinc Reflux;	85%

2-Nitroso-1-naphthol (132-53-6) + (Benzoylmethylene)triphenylphosphorane (20913-05-7) → 2,2'-Azodi-1-naphthol (111796-66-8) + 1,4-diphenylbut-2-ene-1,4-dione (959-28-4) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
In benzene for 40h; Heating;	A 61.81% B 52.8% C 84.7%

2-Nitroso-1-naphthol (132-53-6) + 5-amino-2,4-diethyl iodide-3-methyl-1-phenyl-1H-pyrazolum[4,5-d][1,3]thiazolum → C35H30N6O2S(2+)*2I(1-)

Conditions	Yield
With piperidine In ethanol for 9h; Condensation; Heating;	84%

2-Nitroso-1-naphthol (132-53-6) + 5-acetylamino-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester (481704-89-6) → 5-[2-(1-hydroxy-naphthalen-2-ylimino)-acetylamino]-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester (481705-21-9)

Conditions	Yield
With piperidine In ethanol Heating;	80%

2-Nitroso-1-naphthol (132-53-6) → 2-nitroso-1-amino-naphthalene (501361-38-2)

Conditions	Yield
With ammonium acetate; ammonium chloride at 115 - 120℃; for 0.666667h;	80%

2-Nitroso-1-naphthol (132-53-6) + N-(5-(cyanomethyl)-1,3,4-oxadiazol-2-yl)benzamide (1357598-10-7) → N-(5-(2-oxo-2H-naphtho[1,2-b][1,4]oxazin-3-yl)-1,3,4-oxadiazol-2-yl)benzamide (1357598-08-3)

Conditions	Yield
Stage #1: 2-Nitroso-1-naphthol; N-(5-(cyanomethyl)-1,3,4-oxadiazol-2-yl)benzamide With piperidine In ethanol for 4h; Reflux; Stage #2: With hydrogenchloride; water In ethanol Cooling with ice;	78%

2-Nitroso-1-naphthol (132-53-6) + N-(5-amino-2-methylthieno[3,4-d]pyrimidin-4-yl)acetamide → N-(5-amino-2-methylthieno[3,4-d]pyrimidin-4-yl)-2-(1-hydroxynaphthalen-2-ylimino)acetamide

Conditions	Yield
With piperidine In ethanol for 8h; Reflux;	76%

3-acetyl benzpyrid-4-imino-2-oxime (870784-48-8) + 2-Nitroso-1-naphthol (132-53-6) → 3-[(1-hydroxy-naphthalen-2-ylimino)-acetyl]-4-imino-3,4-dihydro-1H-quinolin-2-one oxime (870784-80-8)

Conditions	Yield
With piperidine In ethanol for 10h; Heating;	75%

2-acetamido-2-methyl-2H-naphtho[2,3-b][1,4]thiazine-5,10-dione-3-carboxylic acid (1023271-65-9) + 2-Nitroso-1-naphthol (132-53-6) → C26H19N3O6S (1023271-66-0)

Conditions	Yield
With piperidine In ethanol; N,N-dimethyl-formamide for 9h; Heating;	75%

2-Nitroso-1-naphthol (132-53-6) + ethyl acetoacetate (141-97-9) → 3-acetyl-2H-naphtho[1,2-b][1,4]oxazin-2-one

Conditions	Yield
With piperidine In ethanol for 8h; Reflux;	75%

2-Nitroso-1-naphthol (132-53-6) + 2-cyano-N-(naphthalen-1-yl)acetamide (22302-63-2) → N-(naphthalen-1-yl)-2-oxo-2H-naphtho[1,2-b][1,4]oxazine-3-carboxamide

Conditions	Yield
Stage #1: 2-Nitroso-1-naphthol; 2-cyano-N-(naphthalen-1-yl)acetamide With piperidine In ethanol for 4h; Reflux; Stage #2: With hydrogenchloride In water	75%

2-Nitroso-1-naphthol (132-53-6) + chloro(diphenyl)-λ3-iodane → 2-nitroso-2-phenyl-2H-naphthalen-1-one

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 20℃; for 20h;	74%

3a,11a-dihydro-3H,4H-1-thia-4-aza-cyclopenta[b]anthracene-2,5,10,11-tetraone (947313-46-4) + 2-Nitroso-1-naphthol (132-53-6) → 3-(1-hydroxy-naphthalen-2-ylimino)-3a,11a-dihydro-3H,4H-1-thia-4-aza-cyclopenta[b]anthracene-2,5,10,11-tetraone (947313-48-6)

Conditions	Yield
With piperidine In ethanol Heating;	73%

iron(III) chloride hexahydrate + 2-Nitroso-1-naphthol (132-53-6) → tris(1,2-naphthoquinone-2-oximato)iron(III)

Conditions	Yield
In methanol stirring FeCl3 with 3 equiv. of ligand; filtration, washing (MeOH), drying (20°C, 0.5 Torr); elem. anal.;	73%

C18H17N4O3(1+)*I(1-) + 2-Nitroso-1-naphthol (132-53-6) → C28H22N5O4(1+)*I(1-)

Conditions	Yield
With piperidine In ethanol; N,N-dimethyl-formamide Heating;	73%

2-Nitroso-1-naphthol (132-53-6) → 1-hydroxy-2,4-dinitronaphthalene (605-69-6)

Conditions	Yield
With Nitrogen dioxide In benzene at 20℃; for 2h;	70%

2-Nitroso-1-naphthol (132-53-6) → quinoline (91-22-5) + isoquinoline (119-65-3) + α-naphthol (90-15-3) + 1-indene (95-13-6)

Conditions	Yield
at 700℃; under 0.02 Torr;	A 5% B 8% C 70% D 12%

2-Nitroso-1-naphthol (132-53-6) + 5-amino-2,6,7,12-tetraoxo-1,2,3,5,5a,6,7,12,13,13a-decahydro-13,13b-diazacyclopenta[a]naphthacene-4-carbonitrile (497833-40-6) → 5-amino-3-(1-hydroxy-naphthalen-2-ylimino)-2,6,7,12-tetraoxo-1,2,3,5,5a,6,7,12,13,13a-decahydro-13,13b-diaza-cyclopenta[a]naphthacene-4-carbonitrile (497833-83-7)

Conditions	Yield
With piperidine In ethanol Heating;	68%

C16H11NO4S (1019922-37-2) + 2-Nitroso-1-naphthol (132-53-6) → C26H16N2O5S

Conditions	Yield
With piperidine In ethanol Heating;	68%

2-Nitroso-1-naphthol (132-53-6) + 3,9-dimethyl-5,11-dioxo-1,7-diphenyl-2,8-diethyl-5,11-dihydrobenzo[2,3-b;2',3'-b']bis(pyrazolo[4,5-b]-1,4-oxazinium iodide) → C50H38N8O6(2+)*2I(1-)

Conditions	Yield
With piperidine In ethanol for 7h; Reflux;	68%
Multi-step reaction with 2 steps 1: piperidine / ethanol / 7 h / Reflux 2: piperidine / ethanol / 7 h / Reflux View Scheme

Upstream product

• 90-15-3 α-naphthol 
• 524-42-5 1,2-naphthoquinone 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 91-59-8 naphthalen-2-ylamine 
• 765-30-0 Cyclopropylamine 
• 581-89-5 2-nitronaphthalene 

Downstream Products

• 791-28-6 Triphenylphosphine oxide 
• 607-24-9 2-nitro-1-naphthol 
• 481705-21-9 5-[2-(1-hydroxy-naphthalen-2-ylimino)-acetylamino]-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 91-22-5 quinoline 
• 119-65-3 isoquinoline 
• 90-15-3 α-naphthol 
• 95-13-6 1-indene 

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Reactions of the aquapentacyanoferrate(II) ion with 2-Nitroso-1-naphthol (cas 132-53-6) and 2-Nitroso-1-naphthol (cas 132-53-6)-4-sulphonic acid09/30/2019

The aqua ligand of the aquapentacyanoferrate(II) ion was replaced by 2-nitroso-1-naphthol and its sulphonate derivative giving the analogous mononuclear nitrosonaphtholpentacyanoferrate(II) complex in the first stage of the reaction. In the second stage, a cyano-bridged binuclear product was ob...detailed

2-Nitroso-1-naphthol (cas 132-53-6) as a selective reagent for preconcentration of cobalt by vortex assisted combined with solidification of organic droplet and its determination by flame atomic absorption spectrometry09/29/2019

Highly rapid and selective vortex-assisted liquid–liquid microextraction based on solidification of organic drop has been used for determination of cobalt ion. 2-Nitroso-1-naphthol (2N1N) was used as a selective complexing agent to form stable cobalt–2N1N complex which can be extracted with 1-...detailed

Separation, preconcentration and inductively coupled plasma-mass spectrometric (ICP-MS) determination of thorium(IV), titanium(IV), iron(III), lead(II) and chromium(III) on 2-Nitroso-1-naphthol (cas 132-53-6) impregnated MCI GEL CHP20P resin10/01/2019

A simple and effective method is presented for the separation and preconcentration of Th(IV), Ti(IV), Fe(III), Pb(II) and Cr(III) by solid phase extraction on 2-nitroso-1-naphthol impregnated MCI GEL CHP20P resin prior to their inductively coupled plasma-mass spectrometric determinations. The in...detailed

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