2-Nitrophenol

Bezeichnung:2-Nitrophenol

CAS-Nr88-75-5

Englisch Name:2-Nitrophenol

CBNumberCB3854576

SummenformelC6H5NO3

Molgewicht139.11

MOL-Datei88-75-5.mol

Synonyma

2-Nitrophenol

o-Nitrophenol

2-Hydroxynitrobenzol

2-Nitrophenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	43-45 °C
Siedepunkt	214-216 °C
Dichte	1.495
Dampfdruck	1 mm Hg ( 49.3 °C)
Brechungsindex	1.5723
Flammpunkt	108 °C
storage temp.	Store in dark!
Löslichkeit	2 g/L (25°C)
pka	7.17(at 25℃)
Aggregatzustand	Liquid
Farbe	Clear pale yellow
Geruch (Odor)	Aromatic odor
PH	5.0~7.0
Säure-Base-Indikators(pH-Indikatoren)	Colorless (5.0) to yellow (7.0)
Wasserlöslichkeit	2 g/L (25 ºC)
Sensitive	Light Sensitive
Merck	14,6619
BRN	775403
Henry's Law Constant	At 20 °C: 11.1 at pH 8.1, 11.0 at pH 10.2, 8.9 at pH 11.9, 6.7 at pH 13.7 (wetted-wall column-UV, Zhang et al., 2003)
Stabilität	Stable. Incompatible with strong bases, strong oxidizing agents.
Major Application	High voltage capacitors, inks, energetic materials, corrosion inhibitors, fertilizer, food storage, enzyme assays, detecting microorganisms, immunotherapy, drugs
Kosmetik-Inhaltsstoffe Funktionen	HAIR DYEING
InChI	1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H
InChIKey	IQUPABOKLQSFBK-UHFFFAOYSA-N
SMILES	Oc1ccccc1[N+]([O-])=O
LogP	1.77
Dissoziationskonstante	7.23 at 25℃
CAS Datenbank	88-75-5(CAS DataBase Reference)
NIST chemische Informationen	Phenol, 2-nitro-(88-75-5)
EPA chemische Informationen	o-Nitrophenol (88-75-5)

Sicherheit

Kennzeichnung gefährlicher	Xn,T,F
R-Sätze:	22-36/37/38-52/53-33-20/21/22-39/23/24/25-23/24/25-11
S-Sätze:	26-61-45-36/37-16-7-36-28
RIDADR	UN 1663 (NITROPHENOLS (o-, m-, p-))
WGK Germany	2
RTECS-Nr.	SM2100000
Selbstentzündungstemperatur	550 °C
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29089000
Speicherklasse	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1
Giftige Stoffe Daten	88-75-5(Hazardous Substances Data)
Toxizität	LD50 orally in mice, rats: 1.297, 2.828 g/kg, K. C. Back et al., Reclassification of Materials Listed as Transportation Health Hazards (TSA-20-72-3; PB214-270, 1972)

Gefahreninformationscode (GHS)

2-Nitrophenol Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
GELBE KRISTALLE.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger und ätzender Rauche mit Stickstoffoxiden. Reagiert mit starken Säuren, starken Basen und starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Verschlucken.
INHALATIONSGEFAHREN
Eine gesundheitsschädliche Partikelkonzentration in der Luft kann schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt leicht die Augen und die Haut. Beim Verschlucken sind Auswirkungen auf das Blut mit nachfolgender Methämoglobinbildungmöglich.
LECKAGE
Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. NICHT in die Umwelt gelangen lassen. Verschüttetes Material in abgedeckten Behältern sammeln.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R33:Gefahr kumulativer Wirkungen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S7:Behälter dicht geschlossen halten.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
Chemische Eigenschaften
yellow crystalline solid
Verwenden
manufacture of dyes, paint colorings, rubber chemicals, and fungicides. Indicator in 2% alcohol solution. pH: 5.0 colorless, 7.0 yellow, but the color change is not sharp and cannot be used where CO2 is present; as reagent for glucose.
Verwenden
2-Nitrophenol is a building block used as an acid-base indicator and corrosion inhibitor for aluminum-copper alloy. It is also used to make dyes, paint coloring, rubber chemicals, and substances that kill molds.
Verwenden
2-Nitrophenol is an intermediate in dyestuff production and a chemical indicator.
Definition
ChEBI: A member of the class of 2-nitrophenols that is phenol in which one of the hydrogens that is ortho to the hydroxy group has been replaced by a nitro group.
Vorbereitung Methode
2-Chloronitrobenzene in 8.5 % sodium hydroxide solution is heated gradually (exothermic) to 170 ℃ in an autoclave and held there under pressure for 8 h. The resulting solution is cooled and acidified to give the product 2-Nitrophenol in 95 % yield.
Synthesis Reference(s)
Canadian Journal of Chemistry, 67, p. 220, 1989 DOI: 10.1139/v89-037
Tetrahedron, 44, p. 4555, 1988 DOI: 10.1016/S0040-4020(01)86158-5
Allgemeine Beschreibung
Yellow solid. Sinks in and mixes slowly with water.
Air & Water Reaktionen
Water insoluble.
Reaktivität anzeigen
2-Nitrophenol is a yellow, crystalline material, moderately toxic, low melting point (45° C). When heated to decomposition 2-Nitrophenol emits toxic fumes of oxides of nitrogen. In molten form violent reaction with strong alkali (85 % potassium hydroxide) [491 M, 1975, p. 342]. Reaction product with chlorosulfuric acid decomposes violently at room temperature [Vervalin, C. H., Hydrocarbon Proc., 1976, 55(9), p. 321].
Hazard
Toxic by ingestion.
Health Hazard
Inhalation or ingestion causes headache, drowsiness, nausea, and blue color in lips, ears, and fingernails (cyanosis). Contact with eyes causes irritation. Can be absorbed through the intact skin to give same symptoms as for inhalation.
Brandgefahr
Special Hazards of Combustion Products: Toxic and irritating fumes of unburned material and oxides of nitrogen can form in fire.
Environmental Fate
Biological. A microorganism, Pseudomonas putida, isolated from soil degraded 2-nitrophenol to nitrite. Degradation by enzymatic mechanisms produced nitrite and catechol. Catechol subsequently degraded to β-ketoadipic acid (Zeyer and Kearney, 1984). When 2-nitrophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, 100% biodegradation with rapid adaptation was achieved after 7 d (Tabak et al., 1981). In a similar study, 2-nitrophenol degraded rapidly from flooded alluvial and pokkali (organic matter-rich acid sulfate) soils that were inoculated with parathion-enrichment culture containing 5- day-old cultures of Flavobacterium sp. ATCC 27551 and Pseudomonas sp. ATCC 29353 (Sudhaker-Barik and Sethunathan, 1978a). 2-Nitrophenol disappeared completely with the formation of nitrite, particularly in the inoculated soils rather than in the uninoculated soils.
Groundwater. Nielsen et al. (1996) studied the degradation of 2-nitrophenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 2-nitrophenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.05/d and 13.86 d, respectively.
Photolytic. A second-order reaction rate constant of 9 x 10^-13 cm³/moleculesec was reported for the reaction of 2-nitrophenol and OH radicals in the atmosphere (Atkinson, 1985). Chemical/Physical. Oxidation by Fenton’s reagent (hydrogen peroxide and Fe³⁺) produced nitrohydroquinone and 3-nitrocatechol (Andersson et al., 1986). In an aqueous solution (initial pH 5.0), 2-nitrophenol (100 μM) reacted with Fenton’s reagent (35 μM). After 60-min and 4-h, about 50 and 90% of the 2-nitrophenol was destroyed, respectively. The pH of the solution decreased due to the formation of nitric acid (Lipczynska-Kochany, 1991).
läuterung methode
Crystallise 2-nitrophenol from EtOH/water, water, EtOH, *benzene or MeOH/pet ether (b 70-90o). It can be steam distilled. Petrucci and Weygandt [Anal Chem 33 275 1961] crystallised it from hot water (twice), then EtOH (twice), followed by fractional crystallisation from the melt (twice), drying over CaCl2 in a vacuum desiccator and then in a drying pistol. The 4-nitrobenzoate had m 141o (from EtOH). [Beilstein 6 IV 1246.]
Filter für giftige stoffe
The acute Initial Threshold Screening Level (ITSL) for 2-nitrophenol is 18 μg/m3 with 24-hr averaging time.

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