4-Nitrophenol

Bezeichnung:4-Nitrophenol

CAS-Nr100-02-7

Englisch Name:4-Nitrophenol

CBNumberCB7852550

SummenformelC6H5NO3

Molgewicht139.11

MOL-Datei100-02-7.mol

Synonyma

4-Nitrophenol

p-Nitrophenol

4-Hydroxynitrobenzol

4-Nitrophenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	112 °C
Siedepunkt	279 °C(lit.)
Dichte	1,27 g/cm³
Dampfdruck	0.6 mm Hg ( 120 °C)
Brechungsindex	1.5723 (estimate)
Flammpunkt	169 °C
storage temp.	2-8°C
Löslichkeit	ethanol: soluble95%, clear, dark yellow (100 mg/mL)
pka	7.15(at 25℃)
Aggregatzustand	Crystalline Powder, Crystals and/or Chunks
Farbe	Yellow to brown
Wichte	1.479
Geruch (Odor)	Odorless
PH	4.4 (5g/l, H2O, 24℃)(anhydrous substance)
Säure-Base-Indikators(pH-Indikatoren)	5.3(colorless)-7.6(Yellow)
Wasserlöslichkeit	1.6 g/100 mL (25 ºC)
Sensitive	Light Sensitive
maximale Wellenlänge (λmax)	320nm, 405nm
Merck	14,6620
BRN	1281877
Henry's Law Constant	1.63 x 10^-7 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
Stabilität	Stable. Incompatible with strong oxidizing agents, strong bases, organics, combustible material, reducing agents. Combustible.
Major Application	Display device, solar cells, nanoparticles, electrolytic capacitors, lithographic printing plate, leak detection method, falsification-proof security paper, correction fluid, detergent, fertilizer, identifying fresh and stale rice, diapers, detecting lactic acid bacteria, drug delivery, evaluating dental caries activity
CAS Datenbank	100-02-7(CAS DataBase Reference)
NIST chemische Informationen	Phenol, 4-nitro-(100-02-7)
EPA chemische Informationen	p-Nitrophenol (100-02-7)

Sicherheit

Kennzeichnung gefährlicher	Xn,T,F
R-Sätze:	20/21/22-33-39/23/24/25-23/24/25-11
S-Sätze:	28-28A-45-36/37-16-7
RIDADR	UN 1663 6.1/PG 3
WGK Germany	2
RTECS-Nr.	SM2275000
F	8
Selbstentzündungstemperatur	541 °F
TSCA	Yes
HazardClass	6.1
PackingGroup	III
HS Code	29089000
Giftige Stoffe Daten	100-02-7(Hazardous Substances Data)
Toxizität	LD50 orally in mice, rats: 467, 616 mg/kg, K.C. Back et al., Reclassification of Materials Listed as Transportation Health Hazards (TSA-20-72-3; PB214-270, 1972)

Gefahreninformationscode (GHS)

4-Nitrophenol Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE BIS HELLGELBE KRISTALLE
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.
CHEMISCHE GEFAHREN
Kann beim Erhitzen explodieren. Zersetzung beim Erhitzen unter Bildung giftiger Rauche mit Stickstoffoxiden. Mischungen mit Kaliumhydroxid sind explosionsfähig.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20 °C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen, die Haut und die Atmungsorgane. Gelbfärbung der Haut. Möglich sind Auswirkungen auf das Blut mit nachfolgender Methämoglobinbildung. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Hautsensibilisierung führen.
LECKAGE
Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R33:Gefahr kumulativer Wirkungen.
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:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
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.
Beschreibung
4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. Generally, 4-nitrophenol is used in manufacturing of drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes, and to darken leather.
Chemische Eigenschaften
Yellow to tan crystals or powder (mixed α- and β-forms), The (metastable) α-form crystallizes from toluene above 63°C, and the yellow, prismatic β-form crystallizes from toluene below 63°C. 4-Nitrophenol is not steam volatile and is much more soluble in water (30 % at 100°C) than the ortho isomer.
Verwenden
4-Nitrophenol is used in dyestuff and pesticide synthesis, as a fungicide, bactericide, and wood preservative, as a chemical indicator, and as a substrate for experiments on cytochrome P450 2E1.
Application
4-Nitrophenol (4-NP) is used to manufacture pharmaceuticals, fungicides, insecticides, and dyes and to darken leather. Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow. It can be used to prepare 4-aminophenol (4-AP), a key intermediate for the manufacture of analgesic and antipyretic drugs.
Definition
ChEBI: 4-nitrophenol is a member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group. It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate acid of a 4-nitrophenolate.
synthetische
4-Nitrophenol was synthesized from p-nitrochlorobenzene by hydrolysis and acidification. Add 2320-2370L of sodium hydroxide solution with a concentration of 137-140g/L to the hydrolysis pot, and then add 600kg of molten p-nitrochlorobenzene. Heat to 152℃, pressure in the pot is 0.4MPa, then stop heating, the hydrolysis reaction exotherm makes the temperature and pressure rise naturally to 165℃, about 0.6MPa. keep 3h and take sample to check the end point of the reaction, after the reaction is finished, the hydrolysate is cooled to 120℃. Add 600L water and 50L concentrated sulfuric acid to the crystallization pot, press into the above hydrolysis and cool to about 50℃, add concentrated sulfuric acid to make the Congo red test paper purple, continue to cool to 30℃, filter, centrifuge to shake off the water, get more than 90% of 4-nitrophenol about 500kg, 92% yield.
Synthesis Reference(s)
Tetrahedron Letters, 27, p. 1607, 1986 DOI: 10.1016/S0040-4039(00)84326-9
Allgemeine Beschreibung
4-nitrophenol appears as a white to light yellow crystalline solid. Contact may severely irritate skin and eyes. Poisonous by ingestion and moderately toxic by skin contact.
Air & Water Reaktionen
Soluble in hot water and more dense than water.
Reaktivität anzeigen
4-Nitrophenol is a slightly yellow, crystalline material, moderately toxic. Mixtures with diethyl phosphite may explode when heated. Decomposes exothermally, emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Decomposes violently at 279°C and will burn even in absence of air [USCG, 1999]. Solid mixtures of the nitrophenol and potassium hydroxide (1:1.5 mol) readily deflagrate [Bretherick, 5th Ed., 1995].
Hazard
Toxic by ingestion.
Health Hazard
Acute inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis. Contact with the eyes causes irritation.
A study examining the acute effects of 4-nitrophenol from inhalation exposure in rats reported an increase in methemoglobin and corneal opacity.
Tests involving acute exposure of rats and mice have shown 4-nitrophenol to have high toxicity from oral and dermal exposure.
Flammability and Explosibility
Non flammable
Sicherheitsprofil
4-Nitrophenol is used to manufacture drugs, fungicides, insecticides, and dyes and to darken leather. Acute (short-term) inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis (blue color in lips, ears, and fingernails). Contact with eyes causes irritation in humans. No information is available on the chronic (long-term) effects of 4-nitrophenol in humans or animals from inhalation or oral exposure. No information is available on the reproductive, developmental, or carcinogenic effects of 4-nitrophenol in humans. EPA has not classified 4-nitrophenol for potential carcinogenicity.
Stoffwechselwegen
4-[U-14C]Nitrophenol is conjugated as its b-glucoside (ca 22% of applied 14C) and gentiobioside, glc- b(126)-glc-b-4-nitrophenol (ca 64%), while about 7% of the parent remains unchanged in cell suspension cultures of Datura stramonium (L.). Gal-b-4-nitrophenol is found to be a minor metabolite.
läuterung methode
Crystallise 4-nitrophenol from water (which may be acidified, e.g. with N H2SO4 or 0.5N HCl), EtOH, aqueous MeOH, CHCl3, *benzene or pet ether, then dry it in vacuo over P2O5 at 25o. It can be sublimed at 60o/10-4mm. The 4-nitrobenzoate had m 159o (from EtOH). [Beilstein 6 IV 1279.]
Toxicity evaluation
The major hazards has been encountered in the use and handling of 4-nitrophenolstem from its toxicologic properties. 4-Nitrophenol irritates the eyes, skin, and respiratory tract. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methemoglobin which is responsible for methemoglobinemia, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response.

4-Nitrophenol Upstream-Materialien And Downstream Produkte

100-02-7, 4-Nitrophenol Verwandte Suche:

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