2-Naphthol

2-Naphthol Struktur
135-19-3
CAS-Nr.
135-19-3
Bezeichnung:
2-Naphthol
Englisch Name:
2-Naphthol
Synonyma:
naphthalen-2-ol;2-naphthalenol;2-HYDROXYNAPHTHALENE;BETA NAPTHOL;BETA-NAPHTHOL;2-Naphtol;β-Naphthol;B-NAPHTHOL;2-Naftol;BETA NAPHTHO
CBNumber:
CB9336283
Summenformel:
C10H8O
Molgewicht:
144.17
MOL-Datei:
135-19-3.mol

2-Naphthol Eigenschaften

Schmelzpunkt:
120-122 °C(lit.)
Siedepunkt:
285-286 °C(lit.)
Dichte
1,28 g/cm3
Dampfdichte
4.97 (vs air)
Dampfdruck
10 mm Hg ( 145.5 °C)
Brechungsindex
1.5762 (estimate)
Flammpunkt:
153 °C
storage temp. 
Store below +30°C.
Löslichkeit
methanol: soluble1g/10 mL, clear, colorless to light yellow
pka
9.51(at 25℃)
Aggregatzustand
Powder, Crystals or Granules
Farbe
White
Säure-Base-Indikators(pH-Indikatoren)
Non& uorescence (8.5) to blue & uorescence (9.5)
Geruch (Odor)
faint phenol-like odor
Wasserlöslichkeit
1 g/L (20 ºC)
maximale Wellenlänge (λmax)
226nm, 265nm, 275nm, 286nm, 320nm, 331nm
Merck 
14,6384
BRN 
742134
Stabilität:
Stable. Combustible. Dust may form explosive mixture with air. Incompatible with strong oxidizing agents, phenol.
Major Application
Display device, semiconductors, photoimaging materials, inks, toner, chalk, security paper, molding materials, tin plating method, rubber, adhesive, leather, detergent, hair dyes, antimitotic drug, anticancer agent, antiinflammatory agent, treatment of acne vulgaris (pimples) and other dermal ailments (rashes, scratches, blemishes, hair loss), disorders
InChIKey
JWAZRIHNYRIHIV-UHFFFAOYSA-N
LogP
1.89 at 20℃
CAS Datenbank
135-19-3(CAS DataBase Reference)
NIST chemische Informationen
2-Naphthalenol(135-19-3)
EPA chemische Informationen
2-Naphthalenol (135-19-3)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,N
R-Sätze: 20/22-50
S-Sätze: 24/25-61
RIDADR  UN 3077 9/PG 3
WGK Germany  2
RTECS-Nr. QL2975000
8
Selbstentzündungstemperatur 430 °C
TSCA  Yes
HazardClass  9
PackingGroup  III
HS Code  29071590
Giftige Stoffe Daten 135-19-3(Hazardous Substances Data)
Toxizität LD50 orally in Rabbit: 1960 mg/kg LD50 dermal Rabbit > 10000 mg/kg
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 Verursacht schwere Augenschäden. Schwere Augenschädigung Kategorie 1 Achtung P280, P305+P351+P338, P310
H400 Sehr giftig für Wasserorganismen. Kurzfristig (akut) gewässergefährdend Kategorie 1 Warnung P273, P391, P501
Sicherheit
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

2-Naphthol Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD

WEISSE BIS GELBLICHWEISSE KRISTALLE MIT CHARAKTERISTISCHEM GERUCH.

PHYSIKALISCHE GEFAHREN

Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.

ARBEITSPLATZGRENZWERTE

TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).

AUFNAHMEWEGE

Aufnahme in den Körper durch Inhalation des Aerosols, über die Haut und durch Verschlucken.

INHALATIONSGEFAHREN

Eine gesundheitsschädliche Partikelkonzentration in der Luft kann beim Dispergieren schnell erreicht werden.

WIRKUNGEN BEI KURZZEITEXPOSITION

WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt stark die Augen.

WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Möglich sind Auswirkungen auf Nieren, Blut und Augen mit nachfolgenden Nierenschäden, Blutarmut und Linsentrübungen.

LECKAGE

Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. NICHT in die Umwelt gelangen lassen.

R-Sätze Betriebsanweisung:

R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
R50:Sehr giftig für Wasserorganismen.

S-Sätze Betriebsanweisung:

S24/25:Berührung mit den Augen und der Haut vermeiden.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.

Aussehen Eigenschaften

C10H7O. Hellgraues Pulver mit aromatischem Geruch, dunkelt beim Lagern nach.

Gefahren für Mensch und Umwelt

Gesundheitsschädlich beim Einatmen und Verschlucken.
LD50 (oral, Ratte): 1960mg/kg

Schutzmaßnahmen und Verhaltensregeln

Schutzhandschuhe aus Neopren als kurzzeitiger Staubschutz.

Verhalten im Gefahrfall

Trocken aufnehmen, dabei Staubentwicklung vermeiden. In gut verschließbaren Behältern der Entsorgung zuführen.
Wassernebel, Kohlendioxid, Schaum, Pulver.

Erste Hilfe

Nach Hautkontakt: Sofort mit Wasser und Seife abwaschen.
Nach Augenkontakt: Gründlich mit viel Wasser und geöffnetem Lidspalt mindesten 10 Minuten spülen und Arzt konsultieren.
Nach Einatmen: Den Betroffenen an die frische Luft bringen und ruhig lagern.
Nach Verschlucken: Wasser trinken lassen. Kein Erbrechen einleiten. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Verunreinigte Kleidung sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag

Sachgerechte Entsorgung

Laborchemikalienabfälle.

Chemische Eigenschaften

2-Naphthol is a white, crystalline solid. Slight phenolic odor. Darkens in air and on exposure to light. 2-Naphthol [135-19-3] b-naphthol, 2- naphthalenol, 2-hydroxynaphthalene, C10H8O, Mr 144.16, forms colorless plates upon sublimation, which darken on exposure to air or light. Unlike 1-naphthol it is nonvolatile in steam. 2-Naphthol is reduced with sodium or with hydrogen in the presence of a catalyst to give mainly 1,2,3,4-tetrahydro-2-naphthol (unlike 1- naphthol which gives the arylphenol under the same conditions). Oxidation with ferric chloride forms 2,20 -dihydroxy-1,10 -binaphthyl, with any blue coloration indicating the presence of 1- naphthol. Air oxidation at 300℃ with a vanadium pentoxide catalyst also yields 1,10 -bi-2-naphthol, which dehydrates at higher temperature to the oxide and finally decomposes to give benzoic acid. Treatment with sulfuryl chloride in carbon disulfide or with NaOCl – NaOH leads to 1- chloro-2-naphthol, whereas chlorine in sodium carbonate gives 8-chloro-2-naphthol ( plus 1, 10 - bi-2-naphthol). Reaction with phosphorus pentachloride at 150℃ gives 2-chloronaphthalene or at lower temperature, tri-2-naphthyl phosphate (mp 111℃), which can be isolated after treatment of the reaction mixture with alkali. Reaction with one equivalent of bromine in acetic acid gives 1-bromo-2-naphthol, whereas excess bromine yields 1,6-dibromo-2-naphthol. The latter is readily debrominated in dilute mineral acid to yield 6-bromo-2-naphthol. Excess bromine reacts with 2-naphthol at 100℃ to form 1,5,6- tribromo- and 1,3,5,6-tetrabromo-2-naphthol.

Verwenden

2-Naphthol is used in the manufacture of dyes, perfumes, and medicinal organics, and in the production of antioxidants for synthetic rubber.

synthetische

2-Naphthol is produced by caustic fusion of naphthalene-2-sulfonic acid. Typically, the sodium salt of the sulfonic acid is added gradually to 50 % sodium hydroxide liquor at 300℃; the melt is then heated further at 320℃ in a gas-fired iron vessel with vigorous agitation. After completion of the reaction, the melt is run into excess water, possibly including filtrate from the previous batch at a proven tolerable level, and the naphtholate solution is neutralized to pH 8 with dilute sulfuric acid. If the temperature is maintained at >100℃ during neutralization, the crude product comes out of solution as an oil, which is separated, washed with hot water, and distilled under vacuum to give pure 2-naphthol. The molten material is processed through a flaker to give the final product for packaging. The fusion yield is about 80 % of the theoretical value, resulting in an overall yield of 70 % based on naphthalene. Typical specifications for 2-naphthol are clear solution in dilute caustic soda,  mp 120.5℃, and 1-naphthol content<0.3 %.
The newer method of manufacture is economically and environmentally favored in the United States, because despite requiring three stages, it is more amenable to continuous operation with recycle streams. The alkylation and isomerization are carried out up to 240℃ with a phosphoric acid catalyst. Final catalytic oxidation at 90 – 110℃ gives the hydroperoxide, which is cleaved with dilute sulfuric acid to give 2-naphthol in high overall yield in spite of modest oxidation conversion.

Definition

ChEBI: 2-naphthol is a naphthol carrying a hydroxy group at position 2. It has a role as an antinematodal drug, a genotoxin, a human xenobiotic metabolite, a mouse metabolite, a human urinary metabolite and a radical scavenger.

Application

It is used to produce Tobias acid, J acid, 2-hydroxy-3-naphthoic acid and azo dyes, and it is the raw material for rubber antioxidants, mineral dressing agents, fungicides, antiseptics, preservatives, etc.
As feed preservative. In China, it can be used for citrus preservation, the maximum dosage amount is 0.1 g/kg and the residue amount should be no more than 70 mg/kg.
2-Naphthol, also called ?-naphthol, 2-naphthalenol, is the intermediate for plant growth regulator, 2-naphthoxyacetic acid.
As analytic agent, absorbent of ethylene and carbon monoxide, and fluorescence indicator.
Important organic raw material and dye intermediate, used to produce Tobias acid, butyric acid, β-hydroxynaphthoic acid and used to produce N-phenyl-2-naphthylamine, Diafen NN and other antioxidant, organic pigments, and fungicides.
For the detection of bromine, chlorine, chlorate, niobium, copper, nitrite, and potassium. Substrate for fluorometric assay of phenol sulfotransferase. Acid and alkali indicator, dyes, organic synthesis, qualitative determination of allyl alcohol, methanol, chloroform, etc. Absorbent of carbon monoxide, ethanol, and fluorescence indicator. Determination of carbon monoxide, copper, nitrite, and potassium. Ethylene absorbent.

Reaktionen

2-Naphthol is naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols.2-Naphthol converts to 2-naphthalenethiol by reaction with dimethylthiocarbamoyl chloride via the Newman–Kwart rearrangement.

Allgemeine Beschreibung

2-Naphthol (2OH) is a hydroxyarene molecule, which when electronically excited forms strong acid. Excited 2OH dissociates only in water. It has a slight phenolic odor. It is incompatible with strong oxidizing agents, strong bases, acid chlorides and acid anhydrides. It is one of the most commonly used fluorescence dye.

Hazard

See α-naphthol

Health Hazard

Although the toxicity of 2-naphthol is of low order in test animals, ingestion of large amounts may result in nausea, vomiting, diarrhea, abdominal pain, convulsions, and hemolytic anemia. Death may result from respiratory failure. The oral LD50 value in rats is in the range 2000 mg/kg. 2-Naphthol is slightly more toxic than 1-naphthol [9015-3], the oral LD50 value of which is in the range 2500 mg/kg.
Skin contact can produce peeling of the skin and pigmentation.

Brandgefahr

Noncombustible solid.

Sicherheitsprofil

Poison by ingestion, inhalation, and subcutaneous routes. Mutation data reported. A skin and eye irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical. Incompatible with antipyrine, camphor, phenol, ferric salts, menthol, potassium permanganate and other oxidzing materials, urethane.

mögliche Exposition

A potential danger to those involved in rubber antioxidant production, synthesis of dyes; leather processing; fungicides, pharmaceuticals, and perfumes. Used as an antioxidant for fats, oils; as an antiseptic; in insecticides.

Versand/Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

läuterung methode

Crystallise 2-naphthol from aqueous 25% EtOH (charcoal), H2O, *benzene, toluene or CCl4. Alternatively, extract it repeatedly with small amounts of EtOH, followed by dissolution in a minimum volume of EtOH and precipitation with distilled water, then drying over P2O5 under vacuum. It has also been dissolved in aqueous NaOH and precipitated by adding acid (repeat several times), then precipitated from *benzene by addition of heptane. Final purification can be by zone melting or sublimation in vacuo. The 4-nitrobenzoate has m 104o (from EtOH). [Bardez et al. J Phys Chem 89 5031 1985, Kikuchi et al. J Phys Chem 91 574 1987, Beilstein 6 IV 4253.]

Inkompatibilitäten

Dust or powder may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, iron salts; 2,3-dimethyl-1- phenyl-3-pyrazolin-5-one (antipyrine); camphor, phenol, menthol, urethane.

Waste disposal

Mix with flammable solvent and atomize into an incinerator.

2-Naphthol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


2-Naphthol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 785)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
SIMAGCHEM CORP
+86-13806087780
sale@simagchem.com China 17368 58
Hebei Mojin Biotechnology Co., Ltd
+8613288715578
sales@hbmojin.com China 12452 58
Hebei Dangtong Import and export Co LTD
+8615632927689
admin@hbdangtong.com China 998 58
Henan Fengda Chemical Co., Ltd
+8613613820652
info@fdachem.com China 5085 58
hebei hongtan Biotechnology Co., Ltd
+86-86-1913198-3935 +8617331935328
sales03@chemcn.cn China 941 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806
sales@capotchem.com China 29797 60
Dalian Richfortune Chemicals Co., Ltd
0411-84820922 8613904096939
sales@richfortunechem.com China 302 57
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21700 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555 +8617317452075
jack.li@time-chemicals.com China 1807 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714
fandachem@gmail.com China 9354 55

135-19-3(2-Naphthol)Verwandte Suche:


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