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1-HYDROXYNAPHTHALENE

1-Hydroxynaphthalene, with the formula C10H7OH, is a fluorescent white solid used primarily as a precursor in the manufacture of various dyes, pharmaceuticals, and agrochemicals.
1-Hydroxynaphthalene serves as a reagent in several chemical tests, such as Molisch’s test for detecting carbohydrates and the Sakaguchi test for identifying arginine in proteins.
In scientific research, 1-hydroxynaphthalene has been studied for its selective toxicity towards human colorectal tumors and its potential use as an antitumor agent, with its toxicity partially mediated through the accumulation of the compound in tumor tissue.

CAS Number: 90-15-3
EC Number: 201-969-4
Chemical Formula: C10H8O
Molar Mass: 144.17 g/mol

Synonyms: 1-NAPHTHOL, 90-15-3, naphthalen-1-ol, alpha-naphthol, 1-Naphthalenol, 1-Hydroxynaphthalene, NAPHTHOL, Furro ER, Fouramine ERN, Fourrine ERN, Tertral ERN, Basf Ursol ERN, Ursol ERN, Fourrine 99, Nako TRB, Zoba ERN, Durafur developer D, Naphthalenol, alpha-Hydroxynaphthalene, C.I. Oxidation Base 33, .alpha.-Naphthol, 1321-67-1, 1-Naphthyl alcohol, NSC 9586, C.I. 76605, CCRIS 1172, HSDB 2650, .alpha.-Hydroxynaphthalene, 1-napthol, EINECS 201-969-4, CI 76605, CHEBI:10319, AI3-00106, MFCD00003930, WLN: L66J BQ, CHEMBL122617, SGCUT00118, DTXSID6021793, NSC9586, 2A71EAQ389, NSC-9586, to_000072, C11714, AB-131/40232333, DTXCID401793, CI Oxidation Base 33, hydroxynaphthalene, Naphthol-1, Naphthyl-1-ol, CAS-90-15-3, Naphthol, 1-, alpha-Naphthyl alcohol, napthalenol, alpha-napthol, napthyl alcohol, UNII-2A71EAQ389, 1-Naphtyol, naphthalene-1-ol, Naphthol 1, 1-Naphtol, 8 -naphthol, hydroxy naphthalene, (+)-naphthol, 1NP, nchembio791-comp4, 1-Naphthol, Reagent, 1-Naphthol, Purified, Naphth-1-ol, 9, LS-95401, 1-NAPHTOL-, 1-NAPHTHOL [MI], SCHEMBL3416, 1-NAPHTHOL [HSDB], alpha-Naphthol, 1-Naphthol, DULOXETINE IMPURITY D, 33420_RIEDEL, 35825_RIEDEL, N1000_SIAL, N2780_SIAL, 1-Naphthol, Pure PA, 99%, 1-Naphthol, LR, >=99%, 70438_FLUKA, 70442_FLUKA, BDBM23450, 1-Naphthol, BioXtra, >=99%, 4b33, 1-Naphthol, p.a., 99.0%, HY-Y1309, Tox21_202120, Tox21_302768, 1-Naphthol, >=98.0% (GC), BBL011611, STL163337, ZINC00967929, AKOS000118822, CS-W020125, GS-6917, 1-Naphthol, ReagentPlus(R), >=99%, Duloxetine EP Impurity D (1-Naphthol), NCGC00249169-01, NCGC00256563-01, NCGC00259669-01, 1ST000684, DB-259778, ST5214429, 1-Naphthol, SAJ special grade, >=99.0%, 1-Naphthol, Vetec(TM) reagent grade, 98%, DULOXETINE IMPURITY D [USP IMPURITY], N0026, N0864, NS00005331, EN300-19501, 1-Naphthol, PESTANAL(R), analytical standard, A843458, Q408876, J-610055, 1-Naphthol, certified reference material, TraceCERT(R), 1-Naphthol, puriss., for fluorescence, >=99.0% (GC), DULOXETINE HYDROCHLORIDE IMPURITY D [EP IMPURITY], F1908-0108, Z104474036, 1-Naphthol, puriss. p.a., Reag. Ph. Eur., >=99% (GC), InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11, 50356-21-3

1-Hydroxynaphthalene is a organic compound with the formula C10H7OH.
1-Hydroxynaphthalene is a fluorescent white solid.

1-Hydroxynaphthalene differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring.
The naphthols are naphthalene homologues of phenol.

Both isomers are soluble in simple organic solvents.
They are precursors to a variety of useful compounds.

1-Hydroxynaphthalene is a hydroxyl-aromatic compound.
1-Hydroxynaphthalene's thermodynamic properties such as heat capacity, sublimation pressure, vapor pressure, enthalpies of combustion, formation and fusion have been estimated.
The decomposition of 1-Hydroxynaphthalene in aqueous solutions on exposure to gamma radiation has been studied.

The ability of biochar of orange peels in adsorbing 1-Hydroxynaphthalene from water has been investigated.
The activation energy and the reaction rate constant of the enzymatic polymerization of 1-Hydroxynaphthalene using laccase have been reported.

1-Hydroxynaphthalene undergoes hydrogenation in the presence of a rhodium catalyst to form cis,cis 1-decalol.
1-Hydroxynaphthalene is a certified reference material (CRM) certified to International Standards BS EN ISO / IEC 17025 and ISO 17034 under UKAS accreditation.

1-Hydroxynaphthalene is a naphthalene homologue of phenol.
1-Hydroxynaphthalene's most common use is as a precursor to various pesticides and pharmaceuticals.

1-Hydroxynaphthalene is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol.
1-Hydroxynaphthalene is used as biomarkers.

1-Hydroxynaphthalene is used in analytical chemistry as Molisch’s reagent (1-Hydroxynaphthalene dissolved in ethanol) for checking the presence of carbohydrates.
1-Hydroxynaphthalene plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.

The decomposition of 1-Hydroxynaphthalene in aqueous solutions on exposure to gamma radiation has been studied.
The ability of biochar of orange peels in adsorbing 1-Hydroxynaphthalene from water has been investigated.

The activation energy and the reaction rate constant of the enzymatic polymerization of 1-Hydroxynaphthalene using laccase have been reported.
1-Hydroxynaphthalene undergoes hydrogenation in the presence of a rhodium catalyst to form cis,cis 1-decalol.

1-Hydroxynaphthalene, also referred to as 1-hydroxy-naphthalene, is an organic compound obtained from the aromatic hydrocarbon naphthalene.
1-Hydroxynaphthalene exists as a white crystalline solid with a subtle odor and displays high solubility in organic solvents.

Scientific research extensively employs 1-Hydroxynaphthalene across multiple applications.
1-Hydroxynaphthalene serves as a reagent in the synthesis of organic compounds, encompassing polymers, and dyes.

Additionally, 1-Hydroxynaphthalene acts as a catalyst in the polymerization process of vinyl monomers.
Notably, 1-Hydroxynaphthalene plays a vital role as a reactant in the synthesis of 1-naphthylacetic acid and its derivatives.

1-Hydroxynaphthalene is a hydroxyl-aromatic compound.
1-Hydroxynaphthalene is a naphthol carrying a hydroxy group at position.

1-Hydroxynaphthalene's thermodynamic properties such as heat capacity, sublimation pressure, vapor pressure, enthalpies of combustion, formation and fusion have been estimated.
The decomposition of 1-Hydroxynaphthalene in aqueous solutions on exposure to gamma radiation has been studied.

1-Hydroxynaphthalene is a organic compound with the formula C10H7OH.
1-Hydroxynaphthalene is a fluorescent white solid.

1-Hydroxynaphthalene differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring.
The naphthols are naphthalene homologues of phenol.

Both isomers are soluble in simple organic solvents.
They are precursors to a variety of useful compounds.

Derivative of 1-Hydroxynaphthalene; used in the synthesis of various chemicals and as a precursor in the production of dyes, pigments, and pharmaceuticals.
1-Hydroxynaphthalene is particularly important in the manufacture of azo dyes, where it serves as a coupling agent in the diazo coupling reaction to produce colored compounds.

Uses of 1-Hydroxynaphthalene:
1-Hydroxynaphthalene is used to make dyes, intermediates, synthetic perfumes, agrochemicals, drugs, and rubber antioxidants.
1-Hydroxynaphthalene is used in organic synthesis.
1-Hydroxynaphthalene is used in photography; in the hide tanning process; in pyrotechnics for black smoke.

1-Hydroxynaphthalene is used as the sulfate monohydrate salt in oxidation hair dyes to a maximum concentration of 2.0%.
The in-use concentration upon application is 1.0%.

Industry Uses:
Intermediate

Therapeutic Uses:
1-Hydroxynaphthalene was selectively toxic to human colorectal tumors compared to corresponding normal colonic tissue removed at surgery and maintained in short-term organ culture.
Nineteen of 24 tumors studied have shown a significant differential response.

Three human colonic adenocarcinoma xenografts, in the short-term organ culture system, displayed the same response to 1-Hydroxynaphthalene as primary tumors removed at surgery.
1-Hydroxynaphthalene, 1,2- and 1,4-naphthoquinone were also toxic to two human colonic adenocarcinoma cell lines, LoVo and COLO 206.

The selective toxicity of 1-Hydroxynaphthalene is mediated in part through an accumulation of 1-Hydroxynaphthalene in the tumor tissue due to impaired conjugation by the tumor.
The higher concentrations of 1-Hydroxynaphthalene may then exert their toxicity either directly or by formation of naphthoquinones.

Some indirect evidence was obtained for the possible involvement of 1,2- or 1,4-naphthoquinone in the cytotoxicity of 1-Hydroxynaphthalene.
Our studies suggest that further studies are warranted of the possible use of 1-Hydroxynaphthalene or related compounds as antitumor agents.

Other uses:
1-Hydroxynaphthalene is used in each of the following chemical tests, which predate the use of spectroscopic and chromatographic methods:
Molisch's test gives a red- or purple-colored compound to indicate the presence of carbohydrate.
Rapid furfural test turns purple quickly (<30s) if fructose is present, distinguishing 1-Hydroxynaphthalene from glucose.

Sakaguchi test turns red to indicate the presence of arginine in proteins.
Voges–Proskauer test changes color from yellow to red to indicate that glucose is being broken down into acetoin which is used by bacteria for external energy storage.

Applications of 1-Hydroxynaphthalene:
1-Hydroxynaphthalene has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.

1-Hydroxynaphthalene is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol.
1-Hydroxynaphthalene is used as biomarkers.

1-Hydroxynaphthalene has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.

Applications and occurrence:
1-Hydroxynaphthalene is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadolol as well as for the antidepressant sertraline and the anti-protozoan therapeutic atovaquone.
1-Hydroxynaphthalene undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.

1-Hydroxynaphthalene is a metabolite of the insecticide carbaryl and naphthalene.
Along with TCPy, 1-Hydroxynaphthalene has been shown to decrease testosterone levels in adult men.

Action Mechanism of 1-Hydroxynaphthalene:
The mechanism(s) of toxicity of 1-Hydroxynaphthalene and two of 1-Hydroxynaphthalene's possible metabolites, 1,2- and 1,4-naphthoquinone, to freshly isolated rat hepatocytes has been studied.
1-Hydroxynaphthalene and both naphthoquinones exhibited a dose-dependent toxicity to hepatocytes.

1-Hydroxynaphthalene was metabolised by hepatocytes predominantly to its glucuronic acid and sulphate ester conjugates, but small amounts of covalently bound products were also formed. Blebbing on the surface of the hepatocytes was observed following exposure to 1-Hydroxynaphthalene and the naphthoquinones, together with a dose-dependent decrease in intracellular glutathione (GSH), which preceded the onset of cytotoxicity.

The toxicity of 1-Hydroxynaphthalene and the naphthoquinones was potentiated by dicoumarol, an inhibitor of DT-diaphorase (NAD(P)H:quinone oxidoreductase).
This enhanced toxicity was accompanied by a greater amount of surface blebbing, an increased depletion of intracellular GSH, particularly in the case of 1-Hydroxynaphthalene and 1,4-naphthoquinone, and a decreased metabolism of 1-Hydroxynaphthalene to its conjugates with variable effects on the amount of covalently bound products formed.

These results support the suggestion that the toxicity of 1-Hydroxynaphthalene may be mediated by the formation of 1,2-naphthoquinone and/or 1,4-naphthoquinone, which may then be metabolised by one electron reduction to naphthosemiquinone radicals.
These, in turn, may covalently bind to important cellular macromolecules or enter a redox cycle with molecular oxygen thereby generating active oxygen species.
Both of these processes appear to play a role in producing the cytotoxic effects of 1-Hydroxynaphthalene.

Production of 1-Hydroxynaphthalene:
1-Hydroxynaphthalene is prepared by two main routes.

In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysis:
C10H8 + HNO3 → C10H7NO2 + H2O
C10H7NO2 + 3H2 → C10H7NH2 + 2H2O
C10H7NH2 + H2O → C10H7OH + NH3

Alternatively, naphthalene is hydrogenated to tetralin, which is oxidized to 1-tetralone, which undergoes dehydrogenation.

General Manufacturing Information of 1-Hydroxynaphthalene:

Industry Processing Sectors:
All Other Basic Organic Chemical Manufacturing

Reactions of 1-Hydroxynaphthalene:
Some reactions of 1-Hydroxynaphthalene are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.
One consequence of this tautomerism is the Bucherer reaction, the ammonolysis of 1-Hydroxynaphthalene to give 1-aminonaphthalene.

1-Hydroxynaphthalene biodegrades via formation of 1-Hydroxynaphthalene-3,4-oxide, which converts to 1,4-naphthoquinone.

The 4-position of 1-Hydroxynaphthalene is susceptible to electrophilic attack.
This regioselective reaction is exploited in the preparation of diazo dyes, which are form using diazonium salts.
Reduction of the diazo derivatives gives 4-amino-1-Hydroxynaphthalene.

Partial reduction of 1-Hydroxynaphthalene gives the tetrahydro derivative, leaving intact the phenol ring.
Full hydrogenation is catalyzed by rhodium.

Handling and Storage of 1-Hydroxynaphthalene:

Handling:

Personal Protective Equipment (PPE):
Wear appropriate PPE, including gloves, safety goggles, and a lab coat.
Avoid direct contact with skin and eyes.

Ventilation:
Use in a well-ventilated area or fume hood to avoid inhalation of dust or vapors.

Avoidance of Inhalation and Ingestion:
Do not eat, drink, or smoke while handling.
Ensure that handling occurs in a designated area away from food and drink.

Storage:

Containers:
Store in tightly closed containers.

Conditions:
Keep in a cool, dry place, away from heat and direct sunlight.

Compatibility:
Avoid contact with strong oxidizers and acids.

Stability and Reactivity of 1-Hydroxynaphthalene:

Stability:

1-Hydroxynaphthalene is generally stable under recommended storage conditions.
Reactivity:

Chemical Incompatibilities:
Reacts with strong acids, bases, and oxidizing agents.

Decomposition Products:
Decomposition may produce irritating or toxic fumes, such as carbon monoxide and carbon dioxide.

First Aid Measures of 1-Hydroxynaphthalene:

Inhalation:
Move the person to fresh air immediately.
If symptoms persist, seek medical attention.

Skin Contact:
Wash affected area with plenty of water and soap.
Remove contaminated clothing.
If irritation persists, seek medical attention.

Eye Contact:
Rinse eyes immediately with plenty of water for at least 15 minutes, holding the eyelids open.
Seek medical attention if irritation persists.

Ingestion:
Do not induce vomiting.
Rinse mouth with water.

If the person is conscious and alert, give small sips of water.
Seek medical attention immediately.

Firefighting Measures of 1-Hydroxynaphthalene:

Firefighting:

Extinguishing Media:
Use dry chemical, foam, or carbon dioxide (CO2).
Water spray can be used to cool containers.

Firefighting Procedures:
Wear self-contained breathing apparatus and protective clothing.
Avoid inhaling fumes.

Fire and Explosion Hazards:
May produce toxic fumes during combustion.
Keep containers cool to prevent pressure build-up and explosions.

Accidental Release Measures of 1-Hydroxynaphthalene:

Personal Precautions:

Wear appropriate PPE including gloves and a respirator if needed.
Avoid generating dust.

Environmental Precautions:
Prevent the chemical from entering sewers or water sources.

Cleanup Methods:
Use suitable absorbent materials to contain and clean up spills.
Dispose of the waste according to local regulations.

Exposure Controls/Personal Protection of 1-Hydroxynaphthalene:

Exposure Limits:
Check local regulations for specific exposure limits.
Generally, minimize exposure by following standard industrial hygiene practices.

Engineering Controls:
Use local exhaust ventilation or fume hoods.

Personal Protective Equipment:

Respiratory Protection:
Use a dust mask or respirator if necessary.

Hand Protection:
Wear gloves that are resistant to the chemical.

Eye Protection:
Use safety goggles or face shields.

Skin Protection:
Wear protective clothing as needed.

Identifiers of 1-Hydroxynaphthalene:
CAS Number: 90-15-3
Beilstein Reference: 1817321
ChEBI: CHEBI:10319
ChEMBL: ChEMBL122617
ChemSpider: 6739
ECHA InfoCard: 100.001.791
EC Number: 201-969-4
Gmelin Reference: 69192
KEGG: C11714
PubChem CID: 7005
UNII: 2A71EAQ389
CompTox Dashboard (EPA): DTXSID6021793
InChI: InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
Key: KJCVRFUGPWSIIH-UHFFFAOYSA-N
InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
Key: KJCVRFUGPWSIIH-UHFFFAOYAZ
SMILES: Oc2cccc1ccccc12

Linear Formula: C10H7OH
CAS Number: 90-15-3
Molecular Weight: 144.17

CAS number: 90-15-3
EC index number: 604-029-00-5
EC number: 201-969-4
Hill Formula: C₁₀H₈O
Chemical formula: C₁₀H₇OH
Molar Mass: 144.17 g/mol
HS Code: 2907 15 10

Properties of 1-Hydroxynaphthalene:
Chemical formula: C10H8O
Molar mass: 144.17 g/mol
Appearance: Colorless or white solid
Density: 1.10 g/cm3
Melting point: 95 to 96 °C (203 to 205 °F; 368 to 369 K)
Boiling point: 278 to 280 °C (532 to 536 °F; 551 to 553 K)
Magnetic susceptibility (χ): -98.2·10−6 cm3/mol

Molecular Weight: 144.17 g/mol
XLogP3: 2.8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 144.057514874 g/mol
Monoisotopic Mass: 144.057514874 g/mol
Topological Polar Surface Area: 20.2Å²
Heavy Atom Count: 11
Complexity: 133
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Boiling point: 288 °C (1013 hPa)
Density: 1.28 g/cm3 (20 °C)
Flash point: 125 °C
Ignition temperature: 510 °C
Melting Point: 95 - 96 °C
Vapor pressure: 2.3 hPa (100 °C)
Bulk density: 450 kg/m3
Solubility: 0.1 g/l

vapor density: 4.5 (120 °C, vs air)
Quality Level: 200
vapor pressure: 1 mmHg ( 94 °C)
product line: ReagentPlus®
Assay: ≥99%
autoignition temp.: 1007 °F
expl. lim.: 5 %
color: white to off-white
bp: 278-280 °C (lit.)
mp: 94-96 °C (lit.)
fluorescence: λex 300 nm; λem 472 nm (Borax buffer)
SMILES string: Oc1cccc2ccccc12
InChI: 1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
InChI key: KJCVRFUGPWSIIH-UHFFFAOYSA-N

Specifications of 1-Hydroxynaphthalene:
Assay (GC, area%): ≥ 99.0 % (a/a)
Melting range (lower value): ≥ 94 °C
Melting range (upper value): ≤ 96 °C
Identity (IR): passes test

Names of 1-Hydroxynaphthalene:

Preferred IUPAC name:
Naphthalen-1-ol

Other names:
1-Hydroxynaphthalene
1-Naphthalenol
α-Naphthol