| Identification | More | [Name]
1-Naphthol | [CAS]
90-15-3 | [Synonyms]
1-HYDROXYNAPHTHALENE
1-naphthalenol
1-NAPHTHOL
AKOS BBS-00004307
ALPHA-HYDROXYNAPHTHALENE
ALPHA-NAPHTHOL
ALPHA-NAPTHOL
a-Naphthol
C.I. 76605
durafur developer d
Fourrine 99
furro er
α-Naphthol
Oxidation base 33
1-naphtol
alpha-naphtol
Basf Ursol ERN
basfursolern
C.I. Oxidation Base 33
c.i.oxidationbase33 | [EINECS(EC#)]
201-969-4 | [Molecular Formula]
C10H8O | [MDL Number]
MFCD00003930 | [Molecular Weight]
144.17 | [MOL File]
90-15-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale grey to brown solid | [Melting point ]
94-96 °C(lit.)
| [Boiling point ]
278-280 °C(lit.)
| [density ]
1.224 | [vapor density ]
4.5 (120 °C, vs air)
| [vapor pressure ]
1 mm Hg ( 94 °C)
| [refractive index ]
1.6224 | [Fp ]
125 °C
| [storage temp. ]
Store in dark! | [solubility ]
Soluble in benzene, chloroform, ether and ethanol. | [form ]
Crystalline Flakes | [pka]
9.34(at 25℃) | [color ]
white to off-white | [Odor]
Slight phenolic odor | [Stability:]
Stable, but air and light sensitive-store under inert gas. Incompatible with strong bases, strong oxidizing agents. | [explosive limit]
5% | [Water Solubility ]
436.7mg/L(25 ºC) | [Sensitive ]
Air & Light Sensitive | [λmax]
324nm(MeOH)(lit.) | [Merck ]
14,6383 | [BRN ]
1817321 | [Contact allergens]
Alpha-naphthol can be used in dye manufacture and is
classified as a hair dye. Combined with epichlorhydrin
and NaOH to form alpha-naphthyl glycidyl ether, it caused
sensitization in one of three workers in a chemical plant. | [InChIKey]
KJCVRFUGPWSIIH-UHFFFAOYSA-N | [LogP]
2.84 at 25℃ | [CAS DataBase Reference]
90-15-3(CAS DataBase Reference) | [NIST Chemistry Reference]
1-Naphthalenol(90-15-3) | [EPA Substance Registry System]
90-15-3(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale grey to brown solid | [Uses]
Used in the manufacturing of dyes, intermediates, synthetic perfumes. | [Definition]
ChEBI: A naphthol carrying a hydroxy group at position 1. | [Hazard]
Toxic by ingestion and skin absorption. | [Description]
Alpha-naphtol, combined with epichlorhydrine and
sodium hydroxide to form alpha-naphtyl glycidyl
ether, caused sensitization in one of three workers in
a chemical plant.
| [Application]
1-Naphthol is a hydroxyl-aromatic compound. It has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model. | [Preparation]
2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%. | [Reactions]
1-Naphthol is reduced by sodium in liquid ammonia to give 5,6,7,8-tetrahydro-1-naphthol; oxidised by NaOCl - FeCl3 or I2-KI to give a purple colour. Phosphorus pentachloride is chlorinated at 150 °C to give 1-chloronaphthalene, thionyl chloride to give 4-chloro-1-naphthol, or Cl2-CH3COOH to give 2,4-dichloro-1-naphthol. Similarly, bromine produces 2,4-dibromo-1-naphthol, a reaction that can be used in quantitative titrations. Its nitration reaction produces a complex mixture. The crude 2,4-dinitro derivative is used as an acidic yellow dye, comparable to picric acid. Sulfonation at 50 °C readily produced 1-naphthol-2,4-disulfonic acid. | [Synthesis Reference(s)]
Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759
Journal of the American Chemical Society, 107, p. 493, 1985 DOI: 10.1021/ja00288a037 | [General Description]
1-Naphthol, a metabolite of carbaryl and naphthanlene. It is formed by spontaneous reaction from (1R, 2S)-Naphthalene epoxide followed to form 1, 4-Dihydroxynaphthalene. | [Flammability and Explosibility]
Notclassified(100%) | [Synthesis]
To a 10 mL pressure vessel, aryl halide (1.00 mmol), copper (I) oxide (0.05 mol), ligand (0.05 mol), 3 M sodium hydroxide (2 mL), and organic solvent (2 mL) were added. The reaction mixture was irradiated at 160 °C for 10 min with strong stirring. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a plug of celite in a fritted filter funnel and washed with ethyl acetate. The product was extracted using 30 mL of ethyl acetate for three times. The organic extract is washed three times with 10 mL water and two times with 10 mL of brine. The combined organic phases were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to afford 1-naphthol. | [storage]
Store at -20°C | [Purification Methods]
Sublime 1-naphthol, then crystallise it from aqueous MeOH (charcoal), aqueous 25% or 50% EtOH, *C6H6, cyclohexane, heptane, CCl4 or H2O. Dry it over P2O5 in vacuo. The 4-nitrobenzoate has m 143o (from EtOH). [Shizuka et al. J Am Chem Soc 107 7816 1985, Beilstein 8 H 596, 6 IV 4208.] |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S2:Keep out of the reach of children . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
1
| [RTECS ]
QL2800000
| [F ]
8-23 | [Autoignition Temperature]
510 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29071510 | [Safety Profile]
Poison by ingestion and
intraperitoneal routes. Moderately toxic by
skin contact. An experimental teratogen.
Experimental reproductive effects. A severe
eye and skin irritant. Mutation data reported.
Ingestion of large amounts can cause
nephritis, vomiting, diarrhea, circulatory
collapse, anemia, convulsions, and death.
Can cause kidney irritation and injury to
cornea and lens of the eye. Combustible
when exposed to heat or flame. When
heated to decomposition it emits acrid
smoke and irritating fumes. | [Hazardous Substances Data]
90-15-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1870 mg/kg LD50 dermal Rabbit 880 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sulfuric acid-->Naphthalene-->1-Naphthylamine-->Naphthalene-2-sulfonic acid-->1,2,3,4-Tetrahydronaphthalene-->2-Ethylnitrobenzene-->Ammonium bisulfate-->1-Chloronaphthalene-->1-Naphthalenesulfonic acid-->Molybdic acid | [Preparation Products]
NAPROANILIDE-->1,4-Naphthoquinone-->Eriochrome Black T-->Napropamide-->2-Ethoxynaphthalene-1-carbonyl chloride-->17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal-->ETHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE-->2-Nitroso-1-naphthol-->METHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE-->3-Methoxy-18-methylestra-2,5(10)dien-17-one 17-ethylene ketal-->6-methoxy-alpha-methylnaphthalen-1-acetaldehyde-->17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methylether-->3-Methoxy-18-methylestra-1,3,5(10),8-tetraen-17-ethylene ketal-->1-Hydroxy-2-naphthoic acid-->sodium 2-[(2-hydroxynaphthyl)azo]naphthalenesulphonate-->fluorescent whitening agent OM-->1-Ethenyl-1,2,3,4-tetrahydro-6-methoxy-1-naphthalenol-->13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one-->N,N'-Di-2-naphthyl-p-phenylenediamine-->6-Methoxy-2-Acetyl Naphthalene-->2-BROMO-1-(6-METHOXY-2-NAPHTHALENYL)-1-PROPANONE-->FLAVIANIC ACID-->N-(1-Naphthyl)ethylenediamine dihydrochloride-->17-Ethynyl-18-methylestra-5(10),9(11)-dien-17-ol-3-one-->ACID RED 1-->1-NAPHTHOXYACETIC ACID-->2-[(1-Naphthyloxy)methyl]oxirane-->2-(1-Naphthalenyloxy)propanoic acid-->1-ETHOXYNAPHTHALENE-->Mordant Black 3-->5,8-Dihydronaphthol-->calcium disodium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]-4-sulphonatobenzoate]-->1-NAPHTHYL CHLOROFORMATE-->1-Nitroso-2-naphthol-->1,6-DIBROMO-2-METHOXYNAPHTHALENE-->4-Amino-1-naphthol hydrochloride-->1,6-Dibromo-2-naphthol-->O-2-Naphthyl chlorothioformate-->1-(6-hydroxy-2-naphthyl)ethan-1-one |
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