2-NITROSO-1-NAPHTHOL supplier

Name
2-Nitroso-1-naphthol
EINECS 205-064-5
CAS No. 132-53-6
Article Data20
CAS DataBase
Density 1.27 g/cm³
Solubility SLIGHTLY SOLUBLE
Melting Point 150-155 °C (dec.)(lit.)
Formula C10H7 N O2
Boiling Point 357.6 °C at 760 mmHg
Molecular Weight 173.171
Flash Point 170.1 °C
Transport Information
Appearance purple-yellow solid.
Safety Moderately toxic by ingestion. Many nitroso compounds are carcinogens. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NO_x. See also NITROSO COMPOUNDS.
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms 1-Naphthol,2-nitroso- (7CI,8CI); 2-Nitroso-1-hydroxynaphthalene; 2-Nitroso-1-naphthalenol;2-Nitroso-1-naphthol; 2-Nitrosonaphthol; C.I. 76610; NSC 5034; b-Nitroso-a-naphthol; b-Nitrosonaphthol
PSA 49.66000
LogP 2.94330

Synthetic route

: 90-15-3
α-naphthol

A: 132-53-6
2-Nitroso-1-naphthol

B: 605-60-7
4-nitroso-1-naphthol

Conditions

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

: 86-48-6
1-hydroxy-2-naphthoic acid

: 132-53-6
2-Nitroso-1-naphthol

Conditions

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;

: 90-15-3
α-naphthol

A: 132-53-6
2-Nitroso-1-naphthol

B: 4965-30-4
1,4-naphthoquinone 1-oxime

Conditions

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%

: 90-15-3
α-naphthol

A: 132-53-6
2-Nitroso-1-naphthol

B: 4-nitroso-2-naphthol

Conditions

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

: 90-15-3
α-naphthol

A: 132-53-6
2-Nitroso-1-naphthol

B: 605-60-7
4-nitroso-1-naphthol

C: 607-24-9
2-nitro-1-naphthol

Conditions

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

...Expand

: 90-15-3
α-naphthol

: 132-53-6
2-Nitroso-1-naphthol

Conditions

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;

: 90-15-3
α-naphthol

: 765-30-0
Cyclopropylamine

A: 132-53-6
2-Nitroso-1-naphthol

B: 605-60-7
4-nitroso-1-naphthol

C: 4-(cyclopropylazo)-1-naphthol

D: 2-(cyclopropylazo)-1-naphthol

Conditions

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

...Expand

: 90-15-3
α-naphthol

A: 132-53-6
2-Nitroso-1-naphthol

B: 4965-30-4
[1,4]naphthoquinone monooxime

Conditions

Conditions	Yield
With potassium nitrite; sulfuric acid
With nitrosylsulfuric acid

: 581-89-5
2-nitronaphthalene

: 132-53-6
2-Nitroso-1-naphthol

Conditions

Conditions	Yield
With potassium carbonate at 55℃;

: 524-42-5
1,2-naphthoquinone

: 132-53-6
2-Nitroso-1-naphthol

Conditions

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

: 91-59-8
naphthalen-2-ylamine

: 132-53-6
2-Nitroso-1-naphthol

Conditions

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)

: 132-53-6
2-Nitroso-1-naphthol

: {Co(β.α-C10H6NO2)3}

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: {Co(β.α-C10H6NO2)3}

Conditions

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%

: 132-53-6
2-Nitroso-1-naphthol

: 607-24-9
2-nitro-1-naphthol

Conditions

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

: sodium hexanitrocobaltate(III)

: 132-53-6
2-Nitroso-1-naphthol

: sodium dinitrobis(1,2-naphthoquinone-1-oximato)cobaltate(III)

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: bis(2-nitroso-1-naphtholato)copper(II) monohydrate

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 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

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

: nickel(II) chloride hexahydrate

: 132-53-6
2-Nitroso-1-naphthol

: bis(1-naphthoquinone-2-oximato)nickel(II)

Conditions

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%

: 132-53-6
2-Nitroso-1-naphthol

: 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

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

: 132-53-6
2-Nitroso-1-naphthol

: 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

Conditions	Yield
With acetic acid; zinc Reflux;	85%

: 132-53-6
2-Nitroso-1-naphthol

: 20913-05-7
(Benzoylmethylene)triphenylphosphorane

A: 111796-66-8
2,2'-Azodi-1-naphthol

B: 959-28-4
1,4-diphenylbut-2-ene-1,4-dione

C: 791-28-6
Triphenylphosphine oxide

Conditions

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

...Expand

: 132-53-6
2-Nitroso-1-naphthol

: 5-amino-2,4-diethyl iodide-3-methyl-1-phenyl-1H-pyrazolum[4,5-d][1,3]thiazolum

: C35H30N6O2S(2+)*2I(1-)

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 481704-89-6
5-acetylamino-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester

: 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

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	80%

: 132-53-6
2-Nitroso-1-naphthol

: 501361-38-2
2-nitroso-1-amino-naphthalene

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 1357598-10-7
N-(5-(cyanomethyl)-1,3,4-oxadiazol-2-yl)benzamide

: 1357598-08-3
N-(5-(2-oxo-2H-naphtho[1,2-b][1,4]oxazin-3-yl)-1,3,4-oxadiazol-2-yl)benzamide

Conditions

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%

: 132-53-6
2-Nitroso-1-naphthol

: 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

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

: 870784-48-8
3-acetyl benzpyrid-4-imino-2-oxime

: 132-53-6
2-Nitroso-1-naphthol

: 870784-80-8
3-[(1-hydroxy-naphthalen-2-ylimino)-acetyl]-4-imino-3,4-dihydro-1H-quinolin-2-one oxime

Conditions

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

: 1023271-65-9
2-acetamido-2-methyl-2H-naphtho[2,3-b][1,4]thiazine-5,10-dione-3-carboxylic acid

: 132-53-6
2-Nitroso-1-naphthol

: 1023271-66-0
C26H19N3O6S

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 141-97-9
ethyl acetoacetate

: 3-acetyl-2H-naphtho[1,2-b][1,4]oxazin-2-one

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 22302-63-2
2-cyano-N-(naphthalen-1-yl)acetamide

: N-(naphthalen-1-yl)-2-oxo-2H-naphtho[1,2-b][1,4]oxazine-3-carboxamide

Conditions

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%

: 132-53-6
2-Nitroso-1-naphthol

: chloro(diphenyl)-λ3-iodane

: 2-nitroso-2-phenyl-2H-naphthalen-1-one

Conditions

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

: 947313-46-4
3a,11a-dihydro-3H,4H-1-thia-4-aza-cyclopenta[b]anthracene-2,5,10,11-tetraone

: 132-53-6
2-Nitroso-1-naphthol

: 947313-48-6
3-(1-hydroxy-naphthalen-2-ylimino)-3a,11a-dihydro-3H,4H-1-thia-4-aza-cyclopenta[b]anthracene-2,5,10,11-tetraone

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	73%

: iron(III) chloride hexahydrate

: 132-53-6
2-Nitroso-1-naphthol

: tris(1,2-naphthoquinone-2-oximato)iron(III)

Conditions

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-)

: 132-53-6
2-Nitroso-1-naphthol

: C28H22N5O4(1+)*I(1-)

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

: 605-69-6
1-hydroxy-2,4-dinitronaphthalene

Conditions

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

: 132-53-6
2-Nitroso-1-naphthol

A: 91-22-5
quinoline

B: 119-65-3
isoquinoline

C: 90-15-3
α-naphthol

D: 95-13-6
1-indene

Conditions

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

...Expand

: 132-53-6
2-Nitroso-1-naphthol

: 497833-40-6
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

: 497833-83-7
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

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	68%

: 1019922-37-2
C16H11NO4S

: 132-53-6
2-Nitroso-1-naphthol

: C26H16N2O5S

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	68%

: 132-53-6
2-Nitroso-1-naphthol

: 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

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

2-NITROSO-1-NAPHTHOL Chemical Properties

IUPAC Name: 2-Nitroso-1-naphthol
The MF of 2-Nitroso-1-naphthol (132-53-6) is C₁₀H₇NO₂.

The MW of 2-Nitroso-1-naphthol (132-53-6) is 173.17.
Synonyms of 2-Nitroso-1-naphthol (132-53-6): 2-Nitroso-1-naphthol ; 1-Hydroxy-2-nitrosonaphthalene ; 1-Naphthalenol, 2-nitroso- ; 1-Naphthol, 2-nitroso-
Product Categories: Intermediates of Dyes and Pigments;Piperazine derivates;Nitroso Compounds;Nitrogen Compounds;Organic Building Blocks
Form: yellow-greenish to yellow-brownish powder
Index of Refraction: 1.629
EINECS: 205-064-5
Density: 1.27 g/ml
Flash Point: 170.1 °C
Boiling Point: 357.6 °C
Melting Point: 156-158 °C
Water Solubility: slightly soluble
BRN: 1867919

2-NITROSO-1-NAPHTHOL Uses

2-Nitroso-1-naphthol (132-53-6) is used for the determination of cobalt, zirconium, copper, iron and palladium. Can also be used in organic synthesis.

2-NITROSO-1-NAPHTHOL Production

From 1 - naphthol derived by nitrosation. 1. Nitrosation will be sodium hydroxide dissolve in water after the stirring stopped by adding 1 - naphthol. Filtration, the filtrate kept at 0-5 ℃, the Canadian drought sodium nitrite solution, and then slowly adding acetic acid plus end. And then 1:4 diluted hydrochloric acid to adjust pH, so that until the Congo red test paper blue. Control points with the starch iodide test paper and continue to stir for half an hour, filter out the nitration objects to a non-acidic washing up, dry. 2. Remove isomers nitrosation also generates 4 - nitroso--1 - naphthol, can be used to remove non-viable given that the potassium hydroxide dissolved in alcohol after stirring slowly adding the dry Nitrate, this time the reaction temperature maintained at 60 ℃, plus complete, continue stirring 10min. Cooling, filter out the crude, soaked in ethanol, filtering. Finally refined derived products.

2-NITROSO-1-NAPHTHOL Toxicity Data With Reference

orl-rat LD:>500 mg/kg

NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),35.

2-NITROSO-1-NAPHTHOL Consensus Reports

Reported in EPA TSCA Inventory.

2-NITROSO-1-NAPHTHOL 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 NO_x. See also NITROSO COMPOUNDS.
Safety information of 2-Nitroso-1-naphthol (132-53-6):
Hazard Codes Xi
Risk Statements
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany 3
RTECS QL4550000
F 8

Product Name

2-Nitroso-1-naphthol

Synthetic route

2-NITROSO-1-NAPHTHOL Chemical Properties

2-NITROSO-1-NAPHTHOL Uses

2-NITROSO-1-NAPHTHOL Production

2-NITROSO-1-NAPHTHOL Toxicity Data With Reference

2-NITROSO-1-NAPHTHOL Consensus Reports

2-NITROSO-1-NAPHTHOL Safety Profile

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