PRODUCTS

1-NAPHTHOL

1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals, including nadolol and the antidepressant sertraline.
1-Naphthol is employed in analytical chemistry as Molisch's reagent for detecting carbohydrates and in the Sakaguchi test for identifying arginine in proteins.
1-Naphthol undergoes various chemical reactions, including hydrogenation to form cis,cis-1-decalol and azo coupling to produce dyes, demonstrating its versatility in organic synthesis.

CAS Number: 90-15-3
EC Number: 201-969-4
IUPAC Name: naphthalen-1-ol
Chemical Formula: C10H8O

Other names: 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-Naphthol is a organic compound with the formula C10H7OH.
1-Naphthol is a fluorescent white solid.
1-Naphthol 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-Naphthol is a hydroxyl-aromatic compound.
1-Naphthol's thermodynamic properties such as heat capacity, sublimation pressure, vapor pressure, enthalpies of combustion, formation and fusion have been estimated.
The decomposition of 1-naphthol in aqueous solutions on exposure to gamma radiation has been studied.

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

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

1-Naphthol's most common use is as a precursor to various pesticides and pharmaceuticals.
1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol.
1-Naphthol is used as biomarkers.

1-Naphthol is used in analytical chemistry as Molisch’s reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates.
1-Naphthol 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-naphthol in aqueous solutions on exposure to gamma radiation has been studied.
The ability of biochar of orange peels in adsorbing 1-naphthol from water has been investigated.

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

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

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

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

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

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

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

1-Naphthol 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-Naphthol; used in the synthesis of various chemicals and as a precursor in the production of dyes, pigments, and pharmaceuticals.
1-Naphthol 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-Naphthol:
1-Naphthol is used to make dyes, intermediates, synthetic perfumes, agrochemicals, drugs, and rubber antioxidants.
1-Naphthol is used in organic synthesis.
1-Naphthol is used in photography; in the hide tanning process; in pyrotechnics for black smoke.

1-Naphthol 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%.

Therapeutic Uses:
1-Naphthol 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-naphthol as primary tumors removed at surgery.
1-Naphthol, 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-naphthol is mediated in part through an accumulation of 1-naphthol in the tumor tissue due to impaired conjugation by the tumor.
The higher concentrations of 1-naphthol 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-naphthol.
Our studies suggest that further studies are warranted of the possible use of 1-naphthol or related compounds as antitumor agents.

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

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

1-Naphthol 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-Naphthol 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-Naphthol undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.

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

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

1-Naphthol 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-naphthol and the naphthoquinones, together with a dose-dependent decrease in intracellular glutathione (GSH), which preceded the onset of cytotoxicity.

The toxicity of 1-naphthol 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-naphthol and 1,4-naphthoquinone, and a decreased metabolism of 1-naphthol to its conjugates with variable effects on the amount of covalently bound products formed.

These results support the suggestion that the toxicity of 1-naphthol 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-naphthol.

Production of 1-Naphthol:
1-Naphthol 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-Naphthol:
Industry Processing Sectors:
All Other Basic Organic Chemical Manufacturing

Reactions of 1-Naphthol:
Some reactions of 1-naphthol 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-naphthol to give 1-aminonaphthalene.

1-Naphthol biodegrades via formation of 1-naphthol-3,4-oxide, which converts to 1,4-naphthoquinone.
The 4-position of 1-naphthol 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-naphthol.

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