1-Naphthol

Bezeichnung:1-Naphthol

CAS-Nr90-15-3

Englisch Name:1-Naphthol

CBNumberCB0279325

SummenformelC10H8O

Molgewicht144.17

MOL-Datei90-15-3.mol

Synonyma

1-Naphthol

1-Naphthol physikalisch-chemischer Eigenschaften

Schmelzpunkt	94-96 °C(lit.)
Siedepunkt	278-280 °C(lit.)
Dichte	1.224
Dampfdichte	4.5 (120 °C, vs air)
Dampfdruck	1 mm Hg ( 94 °C)
Brechungsindex	1.6224
Flammpunkt	125 °C
storage temp.	Store below +30°C.
Löslichkeit	Soluble in benzene, chloroform, ether and ethanol.
pka	9.34(at 25℃)
Aggregatzustand	Crystalline Flakes
Farbe	white to off-white
Geruch (Odor)	Slight phenolic odor
Explosionsgrenze	5%
Wasserlöslichkeit	436.7mg/L(25 ºC)
maximale Wellenlänge (λmax)	324nm(MeOH)(lit.)
Sensitive	Air & Light Sensitive
Merck	14,6383
BRN	1817321
Stabilität	Stable, but air and light sensitive - store under inert gas. Incompatible with strong bases, strong oxidizing agents.
InChIKey	KJCVRFUGPWSIIH-UHFFFAOYSA-N
LogP	2.84 at 25℃
CAS Datenbank	90-15-3(CAS DataBase Reference)
NIST chemische Informationen	1-Naphthalenol(90-15-3)
EPA chemische Informationen	1-Naphthol (90-15-3)

Sicherheit

Kennzeichnung gefährlicher	Xn,N
R-Sätze:	21/22-37/38-41-51/53
S-Sätze:	22-26-37/39-2-61
RIDADR	UN 2811 6.1/PG 3
WGK Germany	1
RTECS-Nr.	QL2800000
F	8-23
Selbstentzündungstemperatur	510 °C
TSCA	Yes
HazardClass	6.1
PackingGroup	III
HS Code	29071510
Giftige Stoffe Daten	90-15-3(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 1870 mg/kg LD50 dermal Rabbit 880 mg/kg

Gefahreninformationscode (GHS)

1-Naphthol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S2:Darf nicht in die Hände von Kindern gelangen.
Aussehen Eigenschaften
C10H8O; 1-Hydroxynaphtalin. Farbloser Feststoff mit charakteristischem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken. Reizt die Atmungsorgane und die Haut. Gefahr ernster Augenschäden. Schädigt die Leber.
Nicht mit starken Oxidationsmitteln, starken Laugen, Säurehalogeniden und Anhydriden in Berührung bringen.
LD₅₀(oral, Ratte): 1780 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Stäube nicht einatmen.
Trocken aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Schaum, Pulver.
Brennbar. Im Brandfall können gefährliche Brandgase freigesetzt werden.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Gelöst in z.B. Aceton als halogenfreie, organische Lösemittelabfälle.
Beschreibung
1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant.
Chemische Eigenschaften
1-Naphthol is a light grey to brown solid with an unpleasant phenol odour, vapour volatility and sublimation. The compound darkens on exposure to air or light and evaporates with water vapour. Soluble in ethanol, ether, benzene, chloroform and alkali solutions, insoluble in water. In contact with ferric chloride produces a purple precipitate.
Verwenden
1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.
synthetische
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%.
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.
Definition
ChEBI: 1-naphthol is a naphthol carrying a hydroxy group at position 1. It has a role as a genotoxin and a human xenobiotic metabolite.
Reaktionen
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
Allgemeine Beschreibung
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.
Hazard
Toxic by ingestion and skin absorption.
Flammability and Explosibility
Not classified
Kontakt-Allergie
1-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.
Sicherheitsprofil
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.
Synthese
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.
läuterung methode
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.]

1-Naphthol Upstream-Materialien And Downstream Produkte

1-Naphthol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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